Episode 12: Toptal’s Taso Du Val on Finding the Top Distributed Talent

Read more about Taso Du Val in “Inside Toptal’s Distributed Screening Process.”

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When hiring managers interview a candidate for a high-level role, they want to be sure that the person they choose will be productive and able to work well with their prospective team. But what if the hiring process takes place over video chat? A growing number of companies outsource the vetting process to a company like Toptal, a freelance marketplace. Toptal’s CEO Taso Du Val joins us on this episode of the Distributed podcast, with Matt Mullenweg. 

The full episode transcript is below.


Stephen Wolfram on 28 Years of Remote Work

Read more about Stephen Wolfram in “The Machine that Turns Ideas into Real Things.”

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Stephen Wolfram started out on an academic career path, but eventually realized that founding a company would allow him to pursue his scientific work more efficiently. He’s served as a remote CEO of Wolfram Research for the last 28 years. In this episode, Stephen shares with host Matt Mullenweg — another remote CEO — his perspective on the value of geo-distribution, and the processes his partially-distributed company uses to make world-changing software. 

The full episode transcript is below.


Automattic’s Sonal Gupta on Communication and Chaos

Read more about Sonal Gupta in “Welcome to the Chaos.”

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Sonal Gupta leads Automattic’s Other Bets division, a team that builds products that aren’t yet core to Automattic’s business, but keep the company innovating and pushing it to explore new territory. In this episode, Sonal and our host Matt Mullenweg talk about how important communication is in the organized chaos of a fully distributed company.

The full episode transcript is below.


Author Scott Berkun on Managing Distributed Teams with Respect

Read more about Scott Berkun in “Observe, Don’t Surveil: Managing Distributed Teams with Respect.”

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Scott Berkun wrote the book on distributed teams. Literally. He spent a couple of years at Automattic and wrote about his experience as a manager in a distributed company. In this episode, Scott talks about that experience, discusses how things have changed since, and explains how today’s managers can cultivate a shared vision in a distributed team.

The full episode transcript is below.


Matt Mullenweg: I want for you to imagine that you’ve been hired as a manager at a scrappy startup where there are no meetings, no hierarchy — not even an office. How do you make people feel like they’re part of a team? How do you brainstorm, and how do you make sure the work’s getting done? Is it possible to cultivate a shared vision, structure, and goals by only meeting in person twice a year? 

That’s what Scott Berkun faced nine years ago, when I hired him to join a little company called Automattic, which is the parent company of WordPress.com, which I founded in 2005. 

As you know from listening to this podcast, Automattic is fully distributed, with no central office and more than 900 employees working from 68 countries. When Scott joined us, we were quite a bit smaller, we were using IRC instead of Slack, and there was a lot that we were still figuring out.

Scott wrote a book about his experience at Automattic called The Year Without Pants, and since then he’s written a whole bunch of books about management, culture, and how we work. Today he’s a sought-after speaker on creativity and innovation.

I caught up with Scott in Seattle to talk about his experience at Automattic, and everything he’s learned since then. Has the future of work panned out like we first imagined it?

Matt: We used to work together, actually. 

SCOTT BERKUN: We did used to work together. I used to work for you. [laughs]

Matt: Well let’s talk a little bit about how that happened, because that was an interesting arc in the story.

Scott: Yes. That was probably 2009 that you asked me to come to an Automattic Grand Meetup and you wanted me to advise on the team or lack of team structure at the company at the time. That was the first time that we officially were working together. 

Matt: That’s an intriguing hook.

Scott: Yes.

Matt: And I guess that was a point when Automattic was totally flat, right? 

Scott: Yes.

Matt: It was like 50 or 60 people all reporting to me. I don’t know how that worked, actually.

Scott: That’s right, yes. [laughs] 

Matt: I don’t remember.

Scott: We talked a few months later about me joining Automattic as a lead of one of the newly formed teams at the company.

Matt: Before that you had been at Microsoft for a while?

Scott: I was a team lead, a project manager guy for about nine years there and I wrote a book about it, which is — probably how we first knew of each other is that you were on my mailing list that was about project management.

Matt: Oh was that the Art and Science — the Project…

Scott: Yes. That’s how we first titled the book. And then when WordPress launched I used it for my blog and that’s how we got to know each other.

Matt: Can we plug that book really quick? What’s the new title?

Scott: The title is Making Things happen. That’s the title of the book now.

Matt: I highly recommend it. That’s the one with the matches on the cover, right?

Scott: That’s right.

Matt: I really enjoyed that book.

Scott: But that was the beginning of my full-time remote work experience was working for you at Automattic. And I remember one of my biggest reasons for wanting to do it was that it very clear in your mind and in my mind that this was an experiment. Can we bring this experienced manager from a traditional company into a company like Automattic that has all these special things — being remote is one of them — but the high autonomy that every individual employee had — continuous deployment, was another. And then the notion of teams itself was an experiment. And then there was also this other notion that you knew that I was going to write a book about this, which was this other curveball to the whole thing.

Matt: Yeah.

Scott: And that combination of experiments — I love the word experiment, and when you used that word, I felt like no matter how this went, it was going to go well. For one of us, at least.  [laughter]

Matt: Yeah, sometimes those book documentary projects don’t go as well.

Scott: No. The distributed work element wasn’t my greatest concern. I was worried about that but I was more worried about — do my skills as a manager in a traditional company where it’s an open office — you see people everyday. Could those skills transfer well to distributed work and to a far more autonomous culture in terms of the individual’s relationship to their work — how much control they had. I was more concerned about those things than distributed work. 

Matt: I think this is a big concern of a lot of managers who have worked one way their whole career and then might be thinking about joining or starting or working in a distributed fashion. What did you see your superpowers as when you were in these in-person cultures?

Scott: I don’t know that I ever thought I had a superpower. I thought — 

Matt: Well you’re a modest guy so let’s call it “medium-powers,” that made you effective at what you were doing.

Scott: I thought that, and I still think this, that most managers are really not very good at managing. Most people you talk to, when they come home from work, they’re not that happy about how well they’ve been managed — they have complaints. And that may extend out to the way the team is organized or the way the goals for their product has been set. 

I thought that I was a good team manager in that I remembered all of my bad experiences as an employee and I tried to work really hard not to repeat those mistakes. And I gave a lot of autonomy to employees because I was one of those employees who liked a lot of control. Once I’ve earned some trust I wanted to be able to run and go at full speed. And the best managers I had are ones who are comfortable giving me that much control. And I tried to rely on that as a strength coming to Automattic. Because everyone was already independent. I have to start out by saying I may not actually add any value at all. I need to observe first to see how things are going before I have any reason to change anything. 

And that’s a common mistake that new managers make everywhere, that they come in and they’ve got this new salary, this new job title, and it kicks their ego in and now it’s about them — How am I going to change the team, how am I going to change the organization? But you don’t know anything, you don’t know these people, you don’t know what their strengths or weaknesses are, you have no data. 

So the best thing you can do — and this comes up in the book that that was what my strategy was for two months — I’m just a note taker. When we have meetings, I’m just going to take notes. I’m going to observe, I’m going to reflect back. And then little by little, once I have something useful to say, I’ll put it into — well it was IRC then but it’d be Slack now — little by little I’ll just try to show, A, I’m not stupid, B, I’m not trying to get in your way, and C, I may actually have some insight that will help you be more productive or successful or happier. And you have to earn that even if you’re the most senior person on the team or the company or whatever.

Matt: How do those meetings happen?

Scott: Well obviously there weren’t teams yet so there were no meetings. [laughter] So what we agreed to do was — 

Matt: Were those Skype calls? 

Scott: It was all text.

Matt: Everyone would be there at the same time, once a week?

Scott: Yeah. And we would chat about whatever everyone was working on. And it started off really short and little by little we added more structure, then we moved to Skype and then eventually the big breakthrough was we switched to audio! Woohoo! It was a big deal because everyone was fully paying attention.

Matt: We’ve had different experiences on audio meetings.

Scott: Yes…

Matt: Just to define some of those terms…

Scott: Yeah.

Matt: IRC is a text-only chat. 

Scott: Correct.

Matt: Think of it like Slack but with a really old school version, like almost terminal-like interface.

Scott: Old school, yes, old school Slack.

Matt: Skype is a messaging platform plus voice.

Scott: Yup.

Matt: And is that what you did the voice meetings on?

Scott: Yeah. We agreed we’d keep the meetings really short but every communication tool is good for some things and bad for others. And text has the advantage that you have time to think but the downside is that written language takes away a lot of data. You can’t hear someone’s inflection in their voice, or pick up on how loud or quiet they are. There’s a lot of data that you lose. 

And having a moment every week where we were on audio, even if it was just for five minutes or ten minutes, emotionally, in terms of your relationship, in terms of understanding people’s nuances and sense of humor, their sarcasm — you could only get that through audio. And you don’t need that much, you don’t need to have two-hour meetings, but ten minutes a week to hear everyone, what they’re talking about, what they’re excited about — you get more data. And I think that helped us throughout the rest of the week.

Matt: That was enough for you to get what you needed to be an effective manager to this team?

Scott: That was enough to help prove that I had some value. Because people would leave those meetings when they were run well saying “Yeah that took 25 minutes but now I understand what Andy is working on, and I see now that’s going to help me later.” That was 25 good minutes as opposed to the typical way people feel about most meetings, which is [that] it’s about other people, it’s all just FYI, stuff that doesn’t go anywhere and it seems that the person running the meeting cares a lot about having them, even though no one else really is engaged. 

And then little by little it became natural for the team to look to me to set the goals and to help decide what features should be next or what things should be built. But you can’t do that as a leader without having some forum for those things to happen. And that’s what the weekly meeting was for us.

Matt: Is that how you saw managers come up in Microsoft as well or was this a unique approach you created for this opportunity?

Scott: I saw a wide range of styles at Microsoft. And this was more like the style that I preferred. I wanted to start off by trusting everyone and extending trust before I ask them to trust me. That’s just good —  

Matt: That’s a really powerful concept, yeah. 

Scott: That’s good relationship management. But I knew there has to be cadence. That’s the fancy word. There has to be a rhythm. If you’re on a team there’s a rhythm. You think of people who are competitive rowers, and there’s that person at the front of the boat who’s just — their job is just to yell out the rhythm, that’s all that they’re doing, the coxswain, right?

Matt: Yeah. 

Scott: They’re taking up weight on the boat simply to be the person who’s controlling the rhythm. And any team, even if people are working individually for the most part but there’s some things that overlap, someone has to be setting the rhythm for the week, the rhythm for the month, and to help people set their own rhythm for the day. And that’s what I thought my job was.

Matt: One thing I hear a lot about people who have had a lot of experience in a physical office is they get so much value from the kind of drop-in or walking around because you get — what you said you get with just a little bit of audio is an even higher bandwidth, right? If we go text, a little bit, audio better, video more — you can see faces — and then in person. Let’s call that the best. How do you deal with not having that?

Scott: All the claims people make about serendipity, you’ll lose all the serendipity of meeting people in the hallway or — you can replicate all that. That’s what the group chat rooms are for where you jump in and you’re bored and you see all the other people who are procrastinating on something. You don’t see them but you can chat with them. There’s randomness and surprise that can happen in any group situation. 

And all the one-on-one direct, more intimate communication, you have now fifty different tools to do that. You can send someone a private text message. “Hey, it seemed like you were upset in that meeting, should we talk?” Or you can make a Skype call. You have all of these tools to make the equivalent of what I would do at Microsoft, which is to go down to someone’s office and say “Hey, can I talk to you?” and close the door.

Matt: What about when that trust gets broken [and] someone doesn’t follow up on what they say they’re going to do? How does your approach there vary when you were an in-person manager versus being a distributed one?

Scott: I really have become a universalist about this, that as the manager — not even the manager — as a person, if someone has made a commitment to me and they’re not honoring it, part of my first thing to do is check in. “Hey, how’s it going, are you still on track for this thing on Friday?” I’m just checking, is my sense of the world in line with your sense of the world? If you do that periodically, especially when you don’t see them posting on Slack or giving any visible — you have no passive indicators that they’re following up on this…

Matt: So is quietness a warning flag?

Scott: It is a warning. And this is one of the things that I learned from you about Automattic was that if you don’t make your work visible it’s invisible. No one can see it. And if you’re not over — what feels at first like over-sharing — or making sure that your code commits show up in the team channel, [or] whatever you’ve agreed on, then that puts someone who is the manager and the responsibility now going, “Well that person’s been quiet for four days, I have to reach out.”

So my first thing is just to check in. Do we still have the same expectations and view of the world? Yes. That sets me up then to come back two days later and go “Hey, we talked a couple days ago, we have a problem here because if you don’t get this done then Sally can’t get her thing done and now it’s going to cascade. So what’s going on?”

90 percent of the time, there is a reason. “Oh, this other issue came up that was more important, I forgot to mention it to you.” I’m like, “OK, great, now I understand, I can recalibrate.” But someone has to be that check-in maintainer that is driven by whoever is in the leadership role. The hard part is when you check in on someone and they keep — there’s something broken still. They’re not getting their work done, they’re frustrated —  

Matt: Or there are broken things in the past. It was due on Friday and now it’s Tuesday.

Scott: Right. You really want to avoid having deep, personal conflict conversations over text.

Matt: Why? It seems so efficient.

Scott: It’s efficient until it’s only making things worse.

Matt: Ping, Berkun. 

Scott: [laughs] It’s what I mentioned before about what you lose, that you don’t get the nuance that is so important to empathizing and understanding what someone is trying to say. And if I have an employee who [has] some issue that’s going on that’s personal that’s got nothing to do with work, they’re less likely to type that in. 

But if I can get them on the phone and they hear my voice, and I can offer them my true empathy for — “I want you to do well, my job is to see you do well.” They get that empathy. Our brains respond to that more directly through voice and eye contact and facial expression. They’re more likely to respond back and share a little bit more about what’s really going on, which could turn out to be something simple, that the way that I assign work or the way that I make decisions bothers them in some way, but I didn’t know that. And they were afraid to offer that to me before.

Matt: So you created that safe space for that to be communicated.

Scott: Yes. I also think that even if you don’t agree with my point about intimacy, I think that every medium has strengths and weaknesses. And just by switching the medium it changes now what the strengths and weaknesses are going to be. To switch from Slack to SMS, although they both seem like text, there are subtle differences in the way people think and translate what’s in their head into communication. And so whenever I am stuck, I will always try to — and I feel like I don’t really know what’s going on here — try to switch the medium. The one that I always feel is the go-to one if I’m confused is voice. And often it’s faster.

Matt: I think that’s great advice and it’s a cool feature of the new tools, like Slack. They have audio built in so you can initiate a call right there. 

Scott: I have this experience with my friends. We’ll be going back and forth on SMS on something we’re not agreeing about and I know from all my experience at Automattic, I know that sometimes a 30-second phone call — 

Matt: Would fix everything.

Scott: Instead of a 20-minute — yes, we are asynchronous, I’m half watching TV while I’m doing it. But it is 20 minutes of time spent arguing about something that’s a nuance that would be completely obvious if we spoke on the phone for 30 seconds.

Matt: It was interesting, we just had a leadership summit at Automattic. It was a training one, and we decided that the focus for the week would actually be feedback. And in my mind going in, it was more about how to give good feedback, some of what we just talked about. But the facilitators, who were quite good, ended up focusing probably the bulk of it on receiving feedback. Let’s say you’re on the other side of things and you’re getting some feedback over text or something like that, what have you found works well or poorly for that?

Scott: I think that you have to start from separating out your personal identity with the work that you’ve done. 

Matt: Hmm. What does that mean? 

Scott: Well I’m a writer, so that’s the easiest place to start. I’m a writer, I write books. And people write reviews of books and a lot of them are really mean. Making Things Happen has a two star review on Amazon where someone says it was about as useful as a piece of toilet paper or something like that.

Matt: By the way, toilet paper is super useful.

Scott: It is super useful. [laughter] It’s all context-dependent though, right?

Matt: It’s interesting though, every author I know has this where at some point, even if they know they shouldn’t, they’ve read the bad reviews and they can usually quote it word for word.

Scott: Yeah. Oh yeah.

Matt: But maybe you can also quote a really good review but they typically don’t have that same vividness to the probably 10 times more good reviews that it’s gotten.

Scott: Yeah. I read every review. 

Matt: Yeah?

Scott: I think every review… not all the GoodReads ones but every Amazon review, every magazine review, and I feel like that’s part of my job. So I write a book and I do work knowing that there are going to be people who have valid criticisms of what I have made. And it doesn’t necessarily mean that what I did was bad, it just means that there’s many ways to decide what good is. That’s part of the job. 

And I feel like that’s part of the job as a manager, that’s part of the job as a developer, that’s part of the job as a designer. You are making stuff and putting it out into the world. That’s what I mean by splitting out my personal identity as Scott from “I made some thing that someone might not like”, or in the management case, “I made a decision that someone really is upset about.” 

Matt: So if I were to rephrase that — you created something that someone thought was worthy of two stars but that does not mean you, Scott Berkun, are a two-star person.

Scott:  Correct. I might be a two-star person but not just because of — 

Matt: Of this one review.

Scott: Right. Not just because of that book that I wrote or a thing that I did.

Matt: Or a thousand two-star reviews, ya know?

Scott: Sure, yeah.

Matt: That sounds hard though. You even started with saying, “I am a writer.”

Scott: That’s why feedback is hard because we, especially people who are passionate about their work, they don’t have much psychological separation between their identity as a worker and their identity as a human being, and that is a kind of maturity that you need to have. 

The helpful thing [is], I have a curious mind to ask clarifying questions. I’m not going to defend anything. I’m going to run with the assumption that they are correct. There’s something flawed in the decision that I made. But I have to be an investigator now. I have to — “OK, when you say this, do you mean that or that? When you say that you thought the decision was unfair, did you mean it was unfair just to you or to the team or to — ” I have to go into that —  

Matt: That’s a tough one because it can feel aggressive.

Scott: Yes.

Matt: Because on the receiving end it’s like, “Oh I’m doing all this extra work to justify my feedback I’m giving you.”

Scott: Yes. I think you’re pointing out how much trust is required to be a good leader, that I have to somehow convince someone who thinks I have done a lousy job that I genuinely want to learn more about why they feel that way and how they think about it. They have to trust me and I have to have earned that trust, that they’re willing to make themselves vulnerable and telling me more about this very uncomfortable thing.

Matt: So how do you build trust besides giving it? Or is that the only way?

Scott: The last therapist that I saw, she said that that’s the only way. [laughter] 

Matt: Oh! 

Scott: She told me and my wife, we were in marriage counseling, that that is the way. If you want to trust someone, the only way to do that is to give them something that you’re entirely sure you should trust them with. There’s no other way.

Matt: Hmm. That’s powerful and terrifying and everything all at the same time.

Scott: It is, it is. But if I have a dog and I need someone to watch it and you’re the only friend I have around — I’m not sure how good you are with dogs, I can’t half-have you watch the dog. Like, either you’re going to watch the dog or you’re not. Or either I’m going to let you cook a meal for me or not. Or I’m going to let you drive my car or not. There’s no — you can do things to insure and mitigate the dangers but either I am trusting you to do something or I am not.

Matt: I will say also that’s something I learned a lot when you joined because as one of the first middle managers, it was a lot of letting go for me.

Scott: Mhm.

Matt: The book is so interesting, especially looking back at it now, because it was a vignette in time and so much has changed since then. In fact, some things in the book quite embarrass me now. I was like, wow, I can’t believe we did that or like, we were so early in our journey in a lot of ways that the company in a ton of ways is unrecognizable in a way I think is really positive. 

You mentioned earlier that people still ask you about the book, you still get questions about it, so I guess people are still reading it, which is cool. How have those questions changed or what have you seen as the things that you look back and are like, “Oh, I’m glad that that’s better now,” or that we know more now?

Scott: I get asked a fair amount about the genderedness of my point of view. And it’s a regret.

Matt: I think it’s also a mistake I made when creating that team.

Scott: Well, maybe. That’s for you to —  [laughter] I know that — I thought about it in writing the book and I knew the culture of our team was a particular way because of its makeup. I should have put that in some kind of context and I didn’t. And part of that was — the book was supposed to be this insider view and I don’t do that much context-setting about these wider issues in not just tech culture but culture at large. I totally understand that perception and I’ve tried to explain it. I don’t think that was an accurate reflection of the whole company. I was trying to reflect what was going on in my team and I didn’t do enough to set that in some kind of context. I regret that.

But people ask me about the book because they’re switching to a remote company or they’re thinking about going to work for a remote company and they want to understand [what it’s] like. A lot of my answer is I don’t think remote work is that big a deal. I don’t understand why people obsess about it. I was at the gym today walking around the gym, I see people who are on their phones, people who are talking to their friends, they’re not necessarily doing remote work, they’re doing remote interaction with other people. 

Remote is such a part of our culture now. Anytime you’re on your phone, interacting with another person through a screen, and it could be an iPad or a laptop, you’re doing remote work. People do remote work at their non-remote jobs all the time and in some cases it’s 50 or 60 percent of their time at work. 

Matt: They’re not always talking to people presently, they’re often chatting or emailing with them.

Scott: Exactly, yeah.

Matt: They just happen to be in the same building.

Scott: Just email alone, ask people how much time of [their] day is spent on email. Guess what, that’s remote work. Remote work! But somehow there is this phobia and stigma around it that is really still strange to me. There’s this fear of it being this completely different way to work. Now it could be if you took a centralized team and one day just said everyone you’re going to go to different countries on the planet, that would be a radical difference because people’s lives would change. But in terms of how work gets done, we’re already remote workers. Everybody. 

If you do email, if you’re on the — you send text messages, Skype meetings, Zoom calls — to me it’s all remote work. And I try to tell people that and they still think there’s some other magical secret. And I’m like, no, I don’t think your problem with remote work is about the remoteness of it. Your problem with remote work is probably you don’t trust your team, your boss is a micromanager, you don’t have clear roles, you don’t have a good way to define who does what projects or to track them. And that’s got nothing to do with remoteness, that’s just basic competence as a team. 

Matt: I think part of it is it’s tied in with a bunch of other things. I like to say any organization over 25 or 50 is distributed already, they’re just maybe not conscious of it. But people, when they hear remote, they also think “Oh I’m working from home.” And their context of what they do at home is very different from what they do at work and sometimes it’s hard to bridge that. Like, how could I work at home with my cat bugging me all the time, or my kids knocking on the door and wanting to play? So that all gets bundled in with some of that. And some of those are real challenges.

Scott: Sure. Part of the stigma around this topic, it’s there is a totality to it that people feel that somehow they’re going to be forced to do things they don’t want to do. I have friends who commute to work and it takes them an hour and a half to go each way to work. I would never do that. There are so many different styles and formats and the demands on you as a person, what you have to wear as a dress code — No job is perfect for everybody. And so I’m an advocate for remote work, I think there are so many advantages to it, but I would never say that everyone is going to love working remotely all the time. I know this is true at Automattic, that some people join and after they’re there for six months — or any distributed company — they discover some things about their own needs they didn’t know before. They need more social interaction, they need more this or that.

Matt: Yeah. In-office work bundles a lot of things and for many people it also becomes, like you said, part of social — people you get lunch with everyday. It’s your connections outside of your normal circles. It’s maybe, depending on where you work, who you play volleyball with or who you exercise with or all these number of things. I think that’s actually one way that companies draw people in quite a bit. I frequently give the advice when someone joins to get some hobbies, go to some meetup groups, find some things where you can interact with other homo sapiens outside of this remote, computer-mediated interactions. 

Scott: Yeah.

Matt: The people who often have the most trouble with it are [the ones] where it’s their first job out of college.

Scott: Interesting.

Matt: You probably remember some of this. You wind up with this thing where someone is not being as productive after a little while and you’re like — I mean it’s a little silly but like, “Are you leaving the house?” [laughter] “Are you showering in the morning, are you eating things other than pizza?” You do need a level of discipline and an approach to healthy habits.

Scott: That is true.

Matt: Another key point and a prominent feature in the book and your experience at Automattic that you helped create was meetups. So we’re distributed, why do we need to get together?

Scott: That’s a bigger version of the voice comment that I said before about how our brains have old programming, we respond in certain ways regarding intimacy by being around people. Facial expression, body language, sharing a meal together.

Matt: Breaking bread, yeah.

Scott: Breaking bread, yeah, there’s a real power to that that you can’t quite replicate it, not in the same way. And so the meetup thing was something that you offered as a policy. It just so happened that me and my team decided to be the — [laughs]

Matt: To really take off on it.

Scott: To run with it. But I thought it made total sense to me, that at least a couple times a year, get everyone in a room together, and then we could flip the way we work and we could work more like a traditional team and take on a bigger project where we all have to be working on the same thing together for two days. 

There’s a different way you learn to work with each other when you have that kind of commitment. I think that helped us a lot as a team because then we’d go back to our regular style of working but now we just spent two days really working hard on something that stretched our relationship and our working styles in a very important way for us.

Matt: How was your trust before and after those meetups?

Scott: Probably better. This gets back to human psychology again. When you share a house with someone, you share a meal with someone, you trust someone to go get the groceries or pick up the car or do a dozen logistical things that happen to be required. It’s a little bit different than this person that you work with but it’s all through digital and virtual stuff. And I don’t know that a team needed to meet up as often as we did. We probably met three times a year and then there’d always be the grand meetups. That’d be the fourth, but we all really enjoyed it and we were all mostly — we didn’t have kids or families so it just fit our team style for the most part. That would change more as the team got bigger. 

Matt: I think this is probably an independent variable from being distributed or not but I’m a big believer in it, that if you give teams autonomy to try things out, hopefully the best practices then spread organically. And then occasionally you might come down from on high and say okay, everyone must do this. 

Actually the last time I remember that was with Slack because we had portions of the company on IRC and Slack and the network effects of having everyone on the same communication tool was too big, too important to let that be too balkanized. But the initial adoption of Slack was just on a team here or there. 

Scott: Yeah, that’s smart how you’ve managed that. I think the autonomy is really important to creative people and not in a superficial way. I think that their tools are so important. A big corporation that hires programmers and tells them you have to use this old computer or something, that’s a lack of respect for what you hired them to do. They’re going to be really tuned in to what tools are going to make them most efficient. Continuing to have that flexibility as Automattic has grown — that’s a cool thing. A lot of companies struggle with that as they grow.

Matt: One thing that comes up a lot is people not sure how to do — is like, “OK. my team is in five different countries, how do we brainstorm? How do we do that sort of creative frisson that seems much easier to spark when you’re in person and have that white board on the wall?”

Scott: For me, I didn’t struggle with that that much. I felt that if I have good people, and there’s a clear goal, then there will be an abundance of fodder. As long as stuff is being offered, as long as there’s that loop of feedback: idea, opinion, critique, new idea. You’re doing above the bar for most teams at most organizations.

Matt: Similar to one of your earlier answers that maybe it’s not as big a deal as people worry about.

Scott: I don’t think so.

Matt: So they should just try it. 

Scott: I think they should try it. But again the things I mentioned are not common. Talented people? Not common. People who are comfortable offering an idea and getting feedback on it? Not that common. People who are good at giving critique? Those kind of conversations? Most organizations don’t do that well. That’s really the problem to me. And no tool is going to solve that. It’s these other factors that are harder to deal with and probably have a lot to do with you as the boss. 

Matt: I’m a new manager at a distributed company. What should I do every day?

Scott: Lurk where your team communicates. Just lurk, just hang out. Spend an hour not jumping in. It’s very easy to jump in. Just observe. Because you may observe the team is just fine without you jumping in.

Matt: And then do you stack something on top of that later?

Scott: The thing that’s coming to mind is whatever feedback loop you have with each individual person on your team — and there is a set of questions that I developed. It’s in the book. I think the four questions were: what’s going well, what could be going better, what do you want me to do more of, and what do you want me to do less of as a manager? That’s how very one-on-one conversation I’d have — which would be like a half an hour, whatever, once a month or so — would be framed in those four questions. 

Matt: Twenty years from now what percentage of jobs do you think will be distributed?

Scott: Well, so I spent a fair amount of time, not recently, with some of these statistics because I get asked a lot and it’s weird how they measure these things. This will be my way that I dodge the question is to talk about survey design instead.

Matt: Telecommute.

Scott: A lot of the surveys are designed, they ask the question in the sense of you being a hundred percent remote or days where you’re a hundred percent remote. So it’s really weird because there are some companies that have liberal policies for you taking one day a week to telecommute. Is that remote work? Well it is but how does that fit into a percentage, like what you’re asking? It’s a weird thing.

Matt: We can make our own definition here. If you were to pick an integer that was a percentage and let’s say people who work not in an office the vast majority of the time, the plurality of the time…

Scott: Yeah I think all the numbers will go up, to cut to the chase. I think it has to. The tools — I’ve already made the joke that most people are already doing remote work even though they don’t call it that. That’s just continued to grow. The tools will get better and better and all the things that can be done digitally, which is the cliff to get over, the curve to get over before you can do it on your phone or your tablet, will continue to grow as technology gets better.

Matt: So a hundred percent? Wow. 

Scott: Well it can’t be a hundred percent because you don’t want your brain surgeon working remotely or your —  

Matt: There was famously the doctor that wheeled in on one of these iPads-on-a-wheel thing and delivered a terminal diagnosis and the person was upset.

Scott: Yeah. I see. Yeah that’s a tricky one. That’s a whole other case though where —  

Matt: It’s a good chance to switch mediums.

Scott: Yes, that is a good chance to switch mediums. Someone else should’ve given the diagnosis I think. Yeah. But I’m very positive just because I think that more worker autonomy just makes for better work. I really believe that.

Matt: Just pick a number off the top of your head.

Scott: What do you think, this is five percent now? Of jobs that are distributed?

Matt: Sure.

Scott: I don’t know, ten percent? I don’t know, twice that, maybe three times that. 

Matt: So somewhere like 25 to 35 percent?

Scott: Yeah. I think it’d be. And that’s enough for it to be normal.

Matt: All right, we’ll get you on Episode 15,000 of the podcast and we can check it out.

Scott: [laughs] Reserve my slot for that.

Matt: Where can people find you if they want to hear more?

Scott: I am ScottBerkun.com and I’m @Berkun on Twitter.

Matt: Scott, it’s always inspiring. Thank you so much for talking with me.

Scott: Thanks for having me.

Matt: That was Scott Berkun. His latest book is The Dance of the Possible: The Mostly Honest Completely Irreverent Guide to Creativity. You can find him at scottberkun.com. 

Thank you so much for joining us and see you next time.

Automattic’s Cate Huston on Building Distributed Engineering Teams

Read more about Cate Huston in “How to Build and Strengthen Distributed Engineering Teams.”

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

Cate Huston is the Head of Developer Experience at Automattic, where her team is responsible for hiring, onboarding, and retaining some of the best software engineers in the world. In this episode, Cate talks with Matt about what kinds of people thrive on distributed engineering teams, and how team leads can keep their engineers happy, productive, and connected to their colleagues. 

The full episode transcript is below.


MATT MULLENWEG: There are all sorts of approaches to distributed work. Some people work from home or at a café in their neighborhood. Others are digital nomads. I’m Matt Mullenweg, the CEO of Automattic and co-founder of WordPress, and I travel around 300 days out of the year. I appreciate that I get to spend time with my family in Texas, but I love life on the road too, and being able to hang out with friends and colleagues all over the world, and meet WordPress users wherever they might be. One of the nice things about running a fully-distributed company is that even the CEO gets to be just as remote as everyone else. 

Today’s guest is Cate Huston, who is a true digital nomad. All she needs is a cup of tea and a place to set up her laptop and she’s ready to go. Her home base is the city of Cork, in Ireland, but you’re just as likely to find her in any other corner of the globe.

Just because Cate is always moving doesn’t mean she has trouble staying connected. Her role at Automattic requires her to be in close contact with her team, and it’s her job to help make sure that all of her fellow engineers stay connected, too. 

After leading several engineering teams at places like Google and others, Cate became the Head of Developer Experience at Automattic, a team responsible for helping all our engineers at Automattic stay engaged, productive, and professionally fulfilled. 

I knew we had to talk to Cate on this podcast because she lives out the distributed model so fully. She also has a comprehensive point of view on what kinds of engineers excel in distributed environments, and how companies can create the conditions that help engineers thrive.

Alrighty, let’s get started with Cate. 

MATT: Hello Cate, thanks for joining today.

CATE HUSTON: Hi Matt. I’m ready for a one-on-one.

MATT: [laughs] Ahh I forgot to tell you we’re recording it. 

CATE: [laughs] You should warn people about these things.

MATT: For the audience, can you catch us up a little bit on some of your experience that led you to Automattic?

CATE: I worked at Google as a software developer and then spent a year roaming the world and doing my own thing, and then joined a startup and was a questionably-legal migrant in Colombia for a while, and then that startup kind of imploded. And around that time, you sent me a GIF of a raccoon being adorable and I was like, “Okay, he can be my new boss.”

MATT: [laughs] You joined to lead the Mobile Team at Automattic.

CATE: Yeah.

MATT: But that has grown. So talk a little bit about that. 

CATE: I joined towards the end of 2017 to lead the Mobile team, which was amazing. And then after about 18 months I went on rotation to the Jetpack Engineering team, which was also super interesting because, as you know, I’ve been using Jetpack for a long time too. But when that came to an end it was clear that I was more needed elsewhere. So I didn’t back to the Mobile team, and I got to work with you, and rolling out Gutenberg. And now I lead our Developer Experience team. So we work to support our entire developer organization, and that includes owning the engineering-hiring process. 

MATT: What is developer experience at Automattic? I’ve heard of user experience but what does developer experience mean?

CATE: I mean: “What does it mean to be a developer at Automattic, what are the challenges of development at Automattic, what are the challenges of development in a distributed, remote context, how can developers learn from other developers, how can they have the support that they need to chart out their own career path?”

We have a lot of autonomy at Automattic, which I think is amazing, but that autonomy can be a bit overwhelming. So can we turn it for people [from] “Write your own MadLib,” into “Choose your own adventure,” [giving] people that kind of support. Also a critical part of the developer experience is the hiring experience going through into the onboarding experience. So how do we give people in our hiring process a good experience so that they can see if this is the right fit for them and we can see if they are the right fit for us, and how do we carry that through into them joining their team and becoming successful?

So one of the ways that we think about developer experience is — our engineering organization is quite big and we’re only so many people. So what we talk about is, “How do we find the pivot points for individuals in teams so that we can be present at those pivot points and try and make them accelerants where possible?” An example of that is when the team gets a new lead, that’s a pivot point. So we want to be there supporting that new lead, bringing them into the kind of support that we have for dev leads, helping them develop and iterate on their process so that that new lead can take that team to new levels. 

MATT: There are probably some engineers listening right now who would love to be hired at Automattic or another distributed company. What advice would you give to them?

CATE: The first thing I would say is, “Be patient, because I think all distributed hiring processes take a little longer.” I think people feel — I don’t know if it’s true — that they get a stronger signal in a day of face-to-face interviews but I think people feel like they have a stronger signal in a day of face-to-face interviews. 

And distributed companies, you can’t tell really if someone doesn’t show up to work. I mean, you can eventually tell, but it’s much easier to disappear. The level of trust required is much higher. And so there is a portion of the process that is earning that trust. We really believe that people can be successful and we’re looking to make people successful. There is no “prove it again” after you get hired. I think that’s really important.

So the first thing is patience and just understanding that the processes take longer. The other thing is that these jobs tend to be more competitive, especially for more specialist roles. There’s not always as many of them as you might want. So you want to craft what you’re doing a little better. Tell a good story in your cover letter, get excited about that company specifically, not just remote work in general. I’m sure all remote companies get a lot of the kind of applications that we get, which is like “Yeah, I just want a remote job so that I can travel around the world.” And it’s like, “Okay, it’s cool to travel around the world, I do it, you do it, but it’s not easy to do that on top of a full time job.”

MATT: So what’s the key for maintaining high performance, as you do, in all these far-flung locations?

CATE: I get pretty rigid about certain things. Like breakfast, I’m very rigid about. So every morning there’s breakfast and then I – 

MATT: That’s very British.

CATE: [laughs] Very British. British being rigid or breakfast being important?

MATT: I think breakfast.

CATE: [laughs] So I try and carve my day into two four-hour blocks. And I just don’t expect to do anything fun during the week, so I do my tourist-ing on the weekends. I really just go and spend a month in a place and try to live there. And honestly I live like that most of the time. When I’m in Cork, because I live in Cork, I try to do things on the weekend, get away from the computer, go out and see things. So if I’m doing that in a different place, it’s fine.

I have my certain needs, which are pretty minimal, like breakfast and some form of exercise and that’s it. And so I just orient myself on “This is breakfast and here is a place to work, there is tea, and this is how I’m going to get regular exercise,” and then, honestly, that’s fine, that’s all I need. 

I’ve probably paired down these needs over time. I don’t know if I started that way, and it is quite hard if you need more stuff. I think sometimes people want peace and quiet, for example, or they need more social contact or whatever, and things that take more time to build, but for me, a laptop, a pair of headphones, a good amount of tea, everything’s fine.

MATT: When you’re hiring engineers, what are you looking for as part of this process besides obviously some base technical-level skill?

CATE: Probably two really big things. One is the ability to work with the kind of code base that we have. WordPress has been around for a long time, there’s probably still code you wrote floating around in it, and that’s quite hard. Not everybody has the experience, the desire to work with truly legacy code. 

And it is a very complex system. It’s not just about technical capability but it’s also being able to grok the complexity of what we had. And this is something that we saw in the mobile apps as well. We would have people on trial for that. There would be three networking stacks because the mobile apps have to speak to WordPress.com, they have to speak to Jetpack, and they have to speak to every other WordPress site too via XML-RPC. 

There’s just a huge amount of complexity that comes with that. And if somebody has not worked on something that is really complex before then they’re going to have quite a bad time with that. And we want to see how they can adapt to that complexity, how they can work with it, and how they can deliver things. 

The second thing that we pay a lot of attention to is how well do people respond to feedback. We are not really hiring people just for what they’re capable of today, but we see it as a long-term commitment. These people, we want them to stay with us for a long time, right? So we’re also hiring them for their growth and the growth that we believe that they can do. And the best predictor of that is that they respond well to feedback. So if we give people feedback and they take it and multiply it and do a lot better, then we feel way more excited about hiring those people than the people who take the feedback and they’re okay with it. And then of course the people who don’t take the feedback well at all, we reject them.

MATT: How have you grown in learning how to take feedback well?

CATE: The first thing is working on self-awareness. When people are not self-aware, you can’t really connect with them because you are always being indirected by their ego. And so developing your self-awareness is super important, something that I work a lot on.

MATT: What does it mean to be self-aware and how do you develop that?

CATE: Do you tell stories about yourself? Do you have things about yourself that you really need to believe are true but might not be?

MATT: What’s an example?

CATE: Some people want to be seen as really nice or really caring, for example, but they might not be very caring. And so they’ll talk a lot about how caring they are but they’re actually not. And so this gap between the way that somebody talks about themselves and their actions will show you this gap in self-awareness.

MATT: How do you cultivate self-awareness?

CATE: Just disabuse yourself of all your illusions. 

MATT: You make it sound easy.

CATE: No, it’s horrible, it’s a lot of therapy and coaching and just being willing to confront the pieces of yourself where you know you’re not as good as you would like to be. Second thing, broadening your perspective, being more open to possibilities outside your worldview. So reading fiction is demonstrated to make people more empathetic, but then reading a broader variety of fiction written by people who are not like you can also broaden your self-awareness. Cultivating a broader network of people, making sure that you’re connected to diverse voices and people who are not like you. And then traveling outside your comfort zone. We talk about the digital bubbles we live in, but a lot of us also live in physical bubbles. And for me, I spent a lot of time living in Medellin, and existing in my third language was a profound exercise in human limitation and empathy.

MATT: Totally. I’d also say you can travel outside your comfort zone without leaving your city.

CATE: One hundred percent.

MATT: There’s probably parts of your city or places that you haven’t been to, buildings you haven’t gone into, places of worship, neighborhoods, stores, barbershops, that can be a journey as well.

CATE: Totally. I am right now in a part of Cork that I had never been to before today. I did not know it was here. So shedding defensiveness, you know? I think people’s first reaction to feedback is to be defensive. It creates conflict, it means you don’t really learn what’s happening, and it shuts the conversation down or it makes the conversation about your feelings rather than what this person is trying to tell you.

Something my coach always tells me is “get curious.” So learning to be — if something makes you uncomfortable not to shut down but to lean into it and to ask questions and really try and understand it is super helpful. Something that people do here is offer context. So people give you feedback and what you give them back is context. And to a certain extent that’s fair enough but too much context is just a polite way to defend yourself. 

MATT: Someone says, “You need to improve X, Y, and Z.” And you say, “Well this and that and this was going on.” Is that what you mean by context?

CATE: Yes, or maybe like, “Oh, you know, I didn’t like how you responded to X.” And then it’s like, “Okay, but for context this set of things was happening.” It’s not really helpful. It’s also getting ahead of that, right? If you say, “Cate, you’re missing your goals.” And I say, “Now let me give all the reasons why this is hard,” that’s not a healthy conversation between us. Right? 

So I’m always trying to get ahead of that with you and be like, “Okay this is where we’re at, this is what’s going on, this is what I’m worried about, this is what I need your help with,” so that you know that you’re not finding problems and giving to me because I know my own problems, and I am on top of them, and I’m telling you what’s going on and what I need from you, so that you should know that you can trust me.

MATT: Got it.

CATE: Asking for advice is also very helpful in self-awareness. Often people are afraid to give feedback because they don’t want to upset you and they are particularly unwilling to give you feedback if they think you’re doing a good job. It’s like, “No, no, no you’re good, you’re good.” But they might have some advice for you.

MATT: So just changing the word you’re using can change how people respond?

CATE: Totally. We have all these negative connotations about feedback, but feedback is really just your own being-in-the-world and being-at-work, for example, being reflected back to you. And it’s neutral really, or it should be. When I’m writing feedback for somebody, the question that I will ask them when I give it to them is, “Did you feel seen when you read this, did you feel like I see everything that you’re doing that’s great and everything that you’re capable of, and how you can do better?”

MATT: Something I try to remind myself, especially when I’m receiving feedback that might be tough, is that good feedback, and by good I mean it’s thoughtful, is a gift — feedback is a gift. And when you receive that you can use it well or you can use it poorly. And I love what you said around getting curious. That is a nice way to reframe something that might be challenging. 

CATE: Yes. If somebody cares about you enough to tell you that they think you should do better then it means that they believe that you could do better.

MATT: What else is on the list?

CATE: There’s two more. The other one is stop giving advice. [laughter]

MATT: That seems incompatible with receiving advice.

CATE: Most people are way too willing to just give advice without context and often without even understanding what someone is trying to achieve. Declaring a moratorium on advice can at least make us pause and ask questions and get context and reflect back to someone what they’re saying to you. 

And the last one is to own up. If you can admit what’s not going well then it’s much less scary for people to talk about the details of how that didn’t go well or what’s not going well. So again you can just make it easier for people to give you information that you wouldn’t otherwise get. 

So my team doubled in size recently. I put up a post on our P2 and I was like, “Okay, so our team has doubled in size and clearly my job is going to change too, and these are the ways where I currently see myself not doing as well, and what do you think? What do you need from me?” And I asked these structured questions to get feedback around what’s the most useful thing that I do for you or what do you think I should stop doing. 

And I got all this amazing input from my team. And if I hadn’t just straight-up admitted it in public, maybe they would be in private being like, “Ohh, Cate seems really frazzled, I don’t know what I can expect from her, I guess I understand that the team is bigger now…” But they might be afraid to tell me what they were experiencing. Whereas instead, putting it out there and having that conversation together made it a team change and a — My job is just the piece of how our team works and we are all deciding and designing that together.

MATT: I know you’re passionate about engineering management. One area where engineers do this a lot is in code review.

CATE: Right.

MATT: Pull requests, etcetera. So what do you see there and what are you working on or want Automattic to work on there?

CATE: I think code review is a core function of a healthy engineering team. Code review done well is such a powerful collaboration tool because both people, or anybody involved in the code review, is learning what the person who wrote the code did, the questions the other person asked, and the reviewer asked. It’s a structured way to have a conversation about the task itself and also the long-term [project] of the code base.

MATT: What else makes a great engineering culture?

CATE: Something that we used to talk about on the mobile team was that a senior engineer makes the whole team better, but we don’t want to be prescriptive about how people made the team better. That was up to them. There were options, but that was the expectation for everyone on the team. It’s like, you come in, you’re an experienced engineer, we expect you to be making the whole team better in some way, and what that looks like is up to you. 

That captures my aspiration for a great engineering culture because one, it suggests that everybody is additive and two, it suggests that everybody is allowed to be unique. And three, it suggests that everybody has the autonomy and the support to operate from a place of strength.

MATT: How much of this is specific to being distributed? How much of this was true when you were at Google versus what might be different now in a distributed company like Automattic?

CATE: The thing I think about distributed is that it makes the things that are hard explicitly hard. I don’t think it really changes anything.

MATT: Tell me more about that.

CATE: You might say that getting a team to be coherent and inclusive and what have you, is just intrinsically hard. And if you are collocated, then you might say, “Oh no, my team is very coherent, we have lunch together everyday, and we do stand-up together every morning, and every so often we do some group activity together. Our team is very good.” 

Whereas if you’re distributed you’ll be much more intentional about it. You’ll say, “Okay, well now I have a new team, and I want that team to be coherent, so how do I make it coherent? How do I make sure that the team understands what their mandate is? How do I make sure they understand what their priorities are? So how do we really maximize the value of a meetup so that people come away the most aligned that they can be?”

MATT: I think it’s helpful for us to be very real on this and talk about the downsides of distributed as well as some of the upsides, which we cover pretty extensively. So to be real and candid about Automattic, what do you think are our biggest challenges and weak points right now?

CATE: I think that we have not always done a great job of hiring and onboarding senior leadership especially into the distributed context. Sometimes we hire people who see distributed as a thing that needs to be mitigated or worked around, rather than a thing that you work with. I don’t think we’re delivering particularly well right now. I don’t think we’re shipping enough and I don’t think we’re shipping enough user value. 

MATT: Totally.

CATE: And I think we’ve evolved our org chart in ways that have been more disruptive than we realize, and have created a lot of gaps that it’s not clear how we should fill or if we’re going to fill. The way that I think about org charts is that they’re really just our chosen optimization, and we can choose what it is, but we have to manage it. 

And I think the thing about a distributed context is that sometimes you can choose your new optimization but if you don’t do the change management it’s not always as obvious what’s going on. Like if you’re in an office and morale is low, you feel it. But in a distributed context it feels different.

MATT: Cate, those are definitely some good challenges. One that has been on my mind recently is I’ve noticed a lot of negativity in some of the teams and some of the feedback. What are your thoughts on that and where does it come from? What can you do to address it?

CATE: I think people get increasingly negative when they don’t feel heard and when they don’t feel hopeful. And so I have spent a lot of time listening to people be negative, and have them not see the value of things that I’m doing. Hearing them out has always been really important and some people will never come around, and some people just need to feel like they’re heard, and to get some of the context that they may be missing, and to have a reason to hope.

In one of my Quartz articles I wrote about how, in any kind of period of change, the people who struggle most are the low performers and the high performers. And the low performers struggle for very obvious reasons, like, change is difficult for them because it’s potentially threatening. They know they’re not amazing. And so for those people, often you can make change good for them, because hopefully you can help them level up. I don’t believe anybody thinks, “Oh I want to be mediocre at work today.”

But then for the high performers, the things that they struggle with, is that they have found a way to succeed in the system as it is, and so any change seems unnecessary to them because really, the problem is that other people haven’t figured it out the way they have. And so those are people where — they’re to some extent right and to some extent wrong. And so helping them have the context, see the empathy, experience the empathy and see some reason for the change and helping them see a sense of improvement is really, really important, because you need to bring those people with you. 

If your high performers are not bought into what you’re doing, then other people won’t be bought into what you’re doing either. So you spend a lot of time, or I personally have spent a lot of time on the high performers who are like, ‘Yeah but really other people just need to be better.” It’s like, “Well, yeah, they do, and so we’re going to help them be better now by doing these things,” and eventually they’ve seen the value of it. And that has generally brought me a disproportionate amount of credibility with other people on the team. 

MATT: Who might distributed work be excluding that might be more included in an office environment?

CATE: Extroverts. Offices give people a certain amount of structure and community, and in the absence of that you have to create your own, and not everybody can or wants to. Work is really just one part of life. When you talk about distributed work, that’s great, there’s all these things that we can do. But when I onboard people into a distributed context, especially for developers, they don’t tend to struggle with the work aspect of it. 

But what they do struggle with is the life aspect, especially people who have not worked in a distributed context before, or a remote context. They struggle to give themselves the structure in their day. They can start work whenever and so they do, and then they finish work at 2:00 in the morning. And at some point, some people are genuinely nocturnal and — fair play, but most people are not actually nocturnal. And starting your day at 4:00 in the afternoon and working until 2:00 in the morning is maybe not that good for you. It’s normally quite bad for your social life unless you are friends mainly with bats. 

So there’s a bunch of knock-on effects to that, which affects your social life, it affects their life-life, it affects their health, because they’re not getting enough sunlight, exercise, what have you. So as someone’s manager, I care about them as a human being, but I’m not their mom. And so that can be quite hard because often it affects their personal well-being more than it affects their work, but it will ultimately affect their work too.

MATT: How can managers encourage inclusion, especially when they might have people across normal categories that we talk about, but also across countries and everything?

CATE: You have to be explicit and talk about it and measure it. In all our reporting on hiring, you will find the same words, which is “Diversity is more than gender, and gender is not binary.” But this is what we can measure and so we measure it, but then we do almost nothing that is just targeted at women. We just use it as a metric and as an indicator of diversity. And we talk about it very explicitly, constantly. 

And I think being explicit like that is really, really helpful. I think being very vocal that it matters — in tech now, I feel like we have talked about diversity maybe too much, inclusion — not enough. And now if you’re not saying, “Oh inclusion is very important,” then you’re clearly a terrible person. So we’re all saying inclusion is really important, but what are we doing?

And then the final thing is building that human connection and checking in with people. I think there are a lot of things that we miss when we don’t see people in person, and you have to notice when people are quiet. And that actually is something that requires a lot more attention.

MATT: Cate Huston, thank you so much for sharing both the good and the bad about distributed work. I think there’s a lot of wisdom in the things we’ve covered.

CATE: Thank you, Matt. I appreciate you.

MATT: That was Cate Huston. You can follow her on Twitter at @ C-A-T-E-H-S-T-N.

I mentioned earlier that there are different approaches to distributed work. And that’s not just true for travel habits. People with different personality types prefer different levels of socialization, communication styles, and leadership styles. Some managers love to have lots of meetings and others would rather keep things moving in the Slack channel. This diversity of styles can make Cate’s job challenging, and as a leader of distributed teams, it can make mine pretty challenging too. 

But I also think this is one of the things that makes the distributed model so exciting. It’s easier for us to meet people where they’re at and give them a custom work experience that suits their personal style. This ideally makes for happier employees and better work. 

Next time on the Distributed podcast, we’ll be talking to author Scott Berkun, who once worked at Automattic and wrote a book about the experience called The Year Without Pants. I’m going to talk to him about his time as our first Team Lead, and about how the distributed-work landscape has changed in the last seven years. 

Thanks so much for joining us and see you next time. 

Leadership Coach Leo Widrich on Emotional Wellness for Distributed Workers

Read more about Leo Widrich in “How to Stay Connected in a Distributed World.”

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

Leo Widrich co-founded Buffer, the social media management software company, in 2010. But like many founders, the frantic pace and daily stresses of startup life caught up to him. After spending a couple of years in a Buddhist monastery studying mindfulness and learning to build emotional resilience, Leo now coaches other business leaders. In this episode, Leo shares tips for distributed workers on how to build healthy habits and avoid the “loneliness spiral.” 

The full episode transcript is below.


Matt Mullenweg: Imagine starting a company with your buddy, turning it into a multibillion dollar business, and offering a service used by brands all over the world, and then walking away from it all to live in a monastery. That’s exactly what this week’s guest did. We’re going to hear all about why he did it. With the startup Buffer, Leo Widrich has achieved success by any measure. But something was missing. His dissatisfaction with the lifestyle led him to pursue deeper truths that he came to realize cannot be found in the pursuit of material success.

Leo studied Buddhism. He spent some time living with monks, and learned to appreciate an intentionally slow lifestyle. Now, he coaches entrepreneurs and even other coaches with the goal of helping them manage the stresses of their careers with a combination of ancient wisdom and a sprinkling of modern neuroscience. He wants people to learn how to build emotional resilience, and the ability to self-regulate their emotions so they can deal with their issues and avoid the full-scale burnout that he suffered.

Buffer is a remote company, so it’s clear that Leo has a passion for unconventional work arrangements. However, he’s extremely sensitive to potential emotional and psychological pitfalls associated with working from home. In this episode, I learn about the loneliness spiral, what can happen if you don’t exercise your social engagement circuits through regular social contact, and Leo shares a few tools that we can use to care better for ourselves and the people we work with.

Leo Widrich: I started a company called Buffer close to a decade ago with a friend and we worked completely remotely.

Matt: Where were you both when it started?

Leo: We both first lived in Birmingham, U.K., so in England, we both studied there. And then we flew out to San Francisco and said hey, Silicon Valley is the spot. That’s how we got started. And we went through all the startup struggles and ups and downs and a couple of the things that were really wonderful as we built the social media management software. And we did it eventually fully remote also, to a level of transparency where I really wanted to put everything on the table about what was going well and what wasn’t going so well in the business. 

Matt: An unheard of level of transparency. So Buffer publishes its revenues, its salaries, its options. Everything, right?

Leo: Right. That was a real desire for us to bring that level of transparency to the business world to reduce some of the sense of secrecy and some of the sense that this is a fight and make it a little more collaborative. 

Matt: Tell me about the why there. Why were you distributed if you started in the same place? And then why the transparency? And are they related at all?

Leo: I think that the distributed part — we were in San Francisco and the team was growing and I’m sure you know that as the team grows in San Francisco, your office space needs to grow. And we were in the middle of — should we expand and get a new office? And I remember even meeting with some brokers, and the prices, they seemed incredible. And we were like, huh… And some of us were barely even coming to the office. 

And I think that was a moment where we all thought, “Well why don’t we try not being in the same office.” And we had tried that before because of visa problems. So at first that was totally not a choice, we just had to be all over the world because we couldn’t stay in the U.S. My partner, Joel, he was from England, and we had a third cofounder, he was also from England. I was from Austria. So it was really hard for us to actually be in the country, so we had to be distributed.

But eventually it was a question of cost and a question of joy and ease too, right? Like, “Oh, why don’t we get to work from wherever we want to?”

Matt: Great. And when was this?

Leo: It must have been 2013, over six years ago, that we decided — before it was unclear, more like an unwritten rule, because we were so small. But then we decided, no, I think we will allow people to be wherever they want to be and then make that a more official commitment, so to speak. And that was also the time when we did start to be more transparent because we wrote down our values, we were very inspired by a company called Zappos at the time.

Matt: Yeah, of course.

Leo: Right? Tony Hsieh is a real mentor in that space of really defining your values and having your purpose. And that was also one of the things that came out of that. So committing to working remotely and committing to being transparent as a way to share with the world what we are learning and to foster a sense of collaboration and openness.

Matt: What was your biggest lesson from being distributed like that?

Leo: At first it was so wonderful. We were traveling around the world, we got to really live a life as well as we were working. So we weren’t deferring enjoying life, so to speak. But over time for me personally what started to creep in a little more was this sense of loneliness, this sense that I feel not as connected. I don’t need to have a base so I’m not committing to a base, that untethered-ness, the longer it went on, the less enjoyable it became, the more almost-painful it became, I would say.

Matt: When you left Buffer, what was next for you?

Leo: I started to feel like I was hitting a wall. This thing that I always dreamt of, to have a profitable company, to be financially secure, to have a team, like a lot of things that I started to aspire to when I got in touch with this idea of startups early on — I felt that having that success, having some of that financial security — it left me unfulfilled in a lot of other areas. In the sense of deep lasting connection and also just a lack of emotional resilience to deal with the ups and downs that startup life comes with. 

So I felt exhausted and we weren’t quite fully in agreement anymore with my cofounder. And I took that as a sign and said “Maybe this is just no longer the right thing for me.” And I took my hat and I left and it started this really interesting journey from outwardly doing stuff and accomplishing stuff — which was the only thing I knew at the time — to go inward. And I started to go and live in Buddhist monasteries and do some therapy training and really start to understand — “Okay, there is so much I was externally striving for but what’s actually here? What’s this foundation, this house that is my body and my psyche?”

Matt: Wow, that’s a big step. Tell us about this Buddhist monastery.

Leo: It’s a big step and a lot of people at the time, they looked at me and they said, “Oh, you’re crazy.”

Matt: I’m so curious, is there an Uber for monasteries? How do you find where you go? Where did you end up? Just walk me through the whole thing if you don’t mind.

Leo: [laughs] Right, for sure. I started to become very interested and soothed by the writing of a Buddhist monk called Thích Nhất Hạnh, and that is really the person that I think brought me into this world. And he wrote this book called Peace Is Every Step. That was the first book I read. It really touched me. It set something off in me. 

He talked about a sense of living in the world and being in the world without that constant striving. And here I was finding myself striving so much, trying so hard to make something successful, to be successful, and he was challenging that idea. And so I saw him speak in 2013. That was when that was more on the sidelines. I was just learning about this stuff. 

And I was living in New York and there is a monastery called Blue Cliff Monastery in upstate New York that I wanted to check out. And I went there for a few retreats, to see what is this life like that seems the exact opposite from the rapid fire startup life, where these Buddhist monks and nuns were living, going so slowly, barely any agenda on the day, every day. And so it was this very different life, very slow. There was very little content, other than what was bubbling up from within me, right? So it was really making a lot of space.

Matt: So you went from startup founder to — I don’t know if you’d call it a monk but you were at a monastery for several years.

Leo: Right.

Matt: And now you’re like a coach. So you work with clients.

Leo: Yup. I call it emotional resilience training, that’s the tagline I have.

Matt: So assuming that you can’t tell your clients to also go away for two years…

Leo: [laughs] Right.

Matt: What’s a middle ground?

Leo: Yeah, you don’t need to go off for two years. But there needs to be some sense of regularity to coming inward, to coming internal. And that is what allows us to build that muscle of emotional resilience where we can not be so cut off from ourselves in the face of difficulty that happens to us and instead to flow with it, to surf the wave of pain, of anger, of sadness, whatever it is. 

And I started to incorporate that with executive coaching, with a framework that — yeah, and you want to also keep contributing to the world. A lot of people don’t want to just step away. Often times, they can’t, right? They have a family to support, they need to keep working or to have a startup to run. And so it became and it is still becoming this combination of offering this deeper emotional work alongside more dialed-in direction-setting for where you want to take your company or your career or your life.

Matt: Give me an example. You say you need this daily habit. What would be something I could do to start to connect and avoid that burnout?

Leo: If it’s possible to you, I would recommend to find something that is not solitary.

Matt: So not self-meditation?

Leo: Yeah, not self-meditation. I would recommend against that unless that’s the only thing available to you. I would recommend that, if you can, to find a therapist or find a coach or find a mentor in your company that you can have regular conversations. Or even a trusted friend — there is a beautiful practice that people can google, it’s called Empathy Buddy Calls. And if there’s a framework for this — how to have these deeper conversations with a friend because often they — even though we might trust someone or have a great friendship they don’t always go to these deeper levels and it’s a great framework. 

That would be my suggestion, to have some support. And the reason I think this is important is because the very idea to do things alone, especially for the likes of me, are only further perpetuating the way I see the world, that I need to be hyper-independent, that I need to pull myself [up] by my own bootstraps, that it’s about strength and doing things alone. And I find that again, back to an evolutionary science, is not really how we evolved, it’s not how our brains are wired, and it’s not as effective as doing it with another person.

Even when I lived at the monastery, it was so interesting that none of these monks meditate alone. Every meditation is together. And this monk, Thich Nhat Hanh, he emphasizes sangha so much. He says if you don’t have a sangha, which is a Buddhist word for “community,” it’s almost impossible to really go to the depth that you need to go to, to deeply transform within yourself.

Matt: That’s so interesting because I’ve definitely read also — I want to say it was Naval Ravikant who sort of made fun of how Westerners turn solitary things like yoga, meditation, into group activities and team sports.

Leo: Interesting, interesting. Yeah.

Matt: And I forget the exact tweet but I took it to heart a little bit because I do often like to exercise or meditate with at least one friend, if not more, and I was like, “Oh am I doing it wrong?” Maybe I need to be more comfortable being alone. 

Leo: Right. And I can see the point of that too. I can see the point of that. 

Matt: But your advice is different for your clients.

Leo: Absolutely. It has become different. If you had asked me four years ago, I’d been meditating on my own for years and years before going to the monastery. And I agree on the point that if it becomes a sport or if it becomes a co-exercise — that is not what I’m talking about. What I’m talking about is to enter spaces together that have a certain depth where you and I say, “If we were to do this together, I might still have a solitary experience, by you holding space for my experience.”

But from a nervous system perspective, the charge that is needed to allow some of these deeper things to come up through the vagus nerve and through my amygdala — in order for that to be held — the amygdala is the fear center in our brains. For that to be not going all over the place, having a second nervous system there to create a sense of safety, I believe is so extremely vital. 

Matt: So that would be your advice to someone starting out, say, find a buddy and do some of this more mindful activity together?

Leo: Absolutely. If that’s possible then I think it’s — and talk about it. 

Matt: We’ve used the word burnout already. What does that mean to you?

Leo: In the same way that the word stress — I like to use it less so. Because it doesn’t really give us a sense of what underlying thing that is happening. I think I even like to use the word PTSD better. 

Matt: That’s a heavy one.

Leo: Right, for most people that would sound heavy but most of — 

Matt: And it has stress in it.

Leo: And it has stress in it, right. But the interesting thing, when we talk about PTSD, and I don’t talk about the way it’s defined for psychologists, I talk about posttraumatic stress. And maybe we can leave off the “D” of disorder because I don’t really think it’s a disorder. But I think it’s anything that when we feel tense in our bodies, it’s because it’s posttraumatic stress. There has been a certain event in our lives and there may have been in our childhood or there may have been, you know, in a meeting or a presentation, and our brains weren’t able to integrate fully what was going on. 

So I’ll give you a common example. Maybe you’re a founder. You have a meeting with your board, and there is a very heated debate. You’re not getting the buy-in, you’re not getting the agreement for something that you really wished you could do. And you leave this meeting feeling quite distraught, feeling quite activated. Your nervous system is charged, you feel angry or you feel sad or there is something — you’re no longer regulated.

Now most people don’t have a way to resolve that. They have a way to auto-regulate and it’s different from self-regulation. And I’m bringing in a few terms here. But most people then auto-regulate. They have a glass of wine or they have a drink or maybe they watch something on TV to soothe themselves.

Matt: What does auto-regulate mean?

Leo: The way it’s defined in neuroscience terms is our natural, unconscious coping mechanisms to deal with deregulated states. And deregulated states means when we are not relaxed, in a relaxed alertness. So that means eating sweets, right? That’s a common auto-regulation pattern that I have. When things get tough, my mind sometimes goes to the ice cream tub in the freezer. 

Matt: For me it’s a matcha latte. 

Leo: Right, right. [laughs] 

Matt: If I’m tired from the day before I just like — you know, the afternoon comes along and I’m like mmm, matcha latte.

Leo: Right.

Matt: I deserve this.

Leo: Right.

Matt: And I get addicted a little bit to that. I don’t have very much caffeine usually. So it does have a big effect on me.

Leo: Right. And that’s a wonderful example. Auto-regulation doesn’t mean it’s bad. We all have that. It can have extremes, like heroin is auto-regulation in the same way that going for a walk in the forest is auto-regulation, right? It’s things that we don’t think about too much that just come to us that have been ingrained patterns and habits and we do them.

Matt: Is burnout avoidable?

Leo: I think so, when we have self-regulation. So self-regulation is a way to deal with the actual effects of what happened in the meeting and to fully process it, for example, if you go back to the example of the board meeting. The body always keeps the score of whatever we haven’t fully processed. 

And so the more of these episodes you have, and in a startup very quickly you might have a lot of meetings where things don’t go well and if you don’t have the time to self-regulate, to talk through this with a friend or with a therapist or with a coach or somebody or with a partner — some people have very healthy self-regulation coping strategies there, you’re actually getting to the root. 

After the meeting, say I had a hard meeting and you’re my good friend Matt, and we sit down and you ask me, “Hey Leo, how are you doing? You look a little upset, you look a little tired.” And I get to say, “Yeah, I’m so upset, this just sucked, this meeting.” And you reflect that back to me, you help me, and say, “Yeah it just sounds like you weren’t heard and you didn’t feel seen and that sounds like it was very painful,” and you just keep holding space for me. And I might cry because it just makes me so sad and I might shake my fist because I’m so angry, letting the bodily states come in. I can’t shake my fist at the investor in the meeting. 

If I have a chance to self-regulate with someone I trust later on, then something magical happens, then this stuff doesn’t build up and five, ten years in you don’t feel like all of a sudden your body is tense from so many different things, you don’t even know why, and you just need to lie down. And we call it — when really if you looked closely, we could trace it back — that it’s all these individual episodes of moments that haven’t been processed.

Matt: Let’s say that I had a friend who had been through something tough. How can I best hold space for them? 

Leo: The most important thing that you can do to a friend that’s going through a hard time is to offer what neuroscience calls warm accompaniment. It used to be called empathy but empathy has — it’s got a little — empathy is feeling what someone else feels, it doesn’t really encompass anymore what is meant or what makes it understandable.

So warm accompaniment means that you refrain from giving any advice, you’re not trying to fix anything. You’re not trying to tell them about your experience, you’re not saying, “Oh this reminds me of my time when I was sick,” you’re not trying to do anything but ideally — and this is from a practice that I also really enjoy called non-violent communication — you just offer back what you are hearing and that can be as simple as reflecting back the exact words. 

And that’s not always the right thing for people but if you’re just getting started, just saying — if you were doing this with me, Matt, if you said, “I had such a hard day at work,” for me to just say, “Wow, it sounds like it’s been a really hard day for you,” that is the warm accompaniment to be I am right there with you without being carried away by your experience. And so, reflecting back what you heard somebody say, noticing whether you can be present. 

You know, if you get carried away and you might say, “I also had such a hard day at work” and your day was so hard, now we’re not co-regulating. 

Matt: So I shouldn’t try to match it.

Leo: Right.

Matt: Should I say “I know how you feel?”

Leo: “I know how you feel” is sympathizing with another person, it is not warmly accompanying their experience. When someone is having a hard time, what is important to them is to understand, for their nervous system to understand that what they are feeling is okay. And I think that’s what you’re trying to say when you say “I know how you feel.” But more important is to offer up the reflection with warmth so that they can see “Yes, that’s what I’m feeling and this person is not triggered by this so I guess it must be okay and my body can relax a little bit.”

Matt: What are some other examples of warm reflection?

Leo: The main way we use to communicate as mammals is through the tone of voice. And there is a term in neuroscience called prosody that means the emotional content that your voice carries. And there’s thousands of nuances that we have in our voices to communicate how we are feeling without the information or the data of the words we are saying. So the most important thing that you can do is just to — the way you say, “Mmm,” or the way you say “Uh huh,” or the way you say “I get it,” — the emotional content of your voice is the most important signal of safety, and we want to do that with the resonance of our voice. 

And the best way I know how to do this is purely by understanding that you can stay present to cultivate that yourself, right? It’s hard, it’s gonna be hard for you. If you don’t know how to — 

Matt: It’s hard to listen.

Leo: Right? It’s hard to listen if you haven’t had enough listening from yourself for yourself or from somebody else for yourself so you can hold space. So that is the long-term practice. But looking into needs and feelings, guesses from the non-violent communication framework is a really wonderful, specific thing you can do. 

To say, “Are you feeling really upset because there wasn’t enough understanding in this meeting?” So that now the person has a chance to either say, “Yeah, you’re getting me,” and can expand, or can clarify what their experience is and accompany that warmly, and can say, “No, I’m not upset because I wanted understanding, I’m really upset because there is no harmony in this company.” A-ha, it’s not about understanding, it’s about harmony, right? And so now the closer — the more precise we can get to experiences, the more likely our nervous system can discharge this and let go of it.

Matt: The classic book on non-violent communication is by… is it Marshall Rosenberg?

Leo: Marshall Rosenberg, yeah, exactly.

Matt: I would particularly recommend it to anyone who is a manager because I think one of the most important things you can do as a manager is listen to people and really hear them.

Leo: Right, mhm.

Matt: And that’s very difficult. I think especially if you’re a new manager there is a temptation to make it about you.

Leo: Right. When you’re a manager and you haven’t done — All the sudden you work with people and you haven’t done your own inner work and your own inner training, it’s gonna be hard to hold space for people, which to a lot of people is a first when they first become managers. 

Matt: And that’s a lot of what I’ve been thinking about as well, is people who are becoming managers for the first time in distributed organizations. There’s lots of people who are freelancers but when you start to get to managing fifty, a hundred people, in a distributed fashion, there’s just not that much out there about it.

Leo: Totally. 

Matt: You’ve written about something called the loneliness spiral. Can you introduce that for the audience?

Leo: The loneliness spiral is associated with the fact that we have — as mammals evolved to be in groups, we are very unfit to survive alone. When we are alone for too long of a stretch of time many people report to feel a feeling that they name “I feel lonely.” And that feeling is simply our nervous system’s alarm system to say “Hey, if you spend too much time alone you’re not gonna survive in this world. Go make some friends, go be with family, go be with other humans.” And we need that physical touch, really in the same-room interaction for that, often for that feeling to dissipate. 

The problem with the loneliness spiral is not that we feel lonely, the problem is that often times when we feel lonely we feel scared at the same time. And actually even if I feel lonely, what I want to do is go out and meet friends, but if I feel scared now I start doing things, because I’m not able to hold that emotion very well in my body, I end up maybe sitting on the couch, eating more potato chips because that fills me up, and then watching some YouTube videos. 

Matt: It can distract you.

Leo: Exactly. So that can distract you but it’s not taking care of the underlying root cause. The thing that happens over time, if it’s not being acted on, parts of our brain — an author called Stephen Porges, who wrote a book called The Polyvagal Theory — he calls this heart of our nervous system the social engagement circuits. If they are not exercised through a muscle, through regular social engagements, through regular social contact — and this is one of my concerns with remote work — if that’s not exercised it atrophies.

Matt: So we’re talking right now.

Leo: Yeah.

Matt: It sounds pretty good, like you could be right next to me.

Leo: Right.

Matt: Does this also get activated by video calls, by phone calls, those sorts of things, Facetime?

Leo: It does, it does. That is good news for remote work.

Matt: That’s good. Because then I can connect with someone anywhere in the world.

Leo: It’s good news and, and I wonder if you’ve noticed this with remote work, is that most calls are scheduled, right? We are not here to just catch up, you know? We are not here to just tap me on the shoulder and say, “Hey Leo, how are you doing?” by the water cooler, “How was that concert you went to last night?” So the sort of social engagement that I’m talking about, that almost intimacy that can develop that happens most likely when things are unscheduled and spontaneous are much [less likely] to happen.

We have experimented with this at Buffer. We tried to have book clubs and social hangouts on Zoom and what not to create that. And I think that’s often what’s needed beyond the scheduled meetings where there is an agenda and you work through, and the informational content really is a thing, what it’s all about and not the emotional content that really is a thing that trains our nervous systems to know, “Okay, I’m not alone, there’s other humans that care about me, I care about them.” That thing.

Matt: How about if I’m in a crowd? I know personally sometimes I can feel very lonely even though I’m around a lot of people.

Leo: Right, yeah.

Matt: Just going to a coffee shop. But is that gonna help anyway?

Leo: It’s something. [laughs] It’s something but you can still feel very lonely. And my view on that from what I’ve learned about our inner states is that often that social engagement is activated only when we reveal something about ourselves, when we show something about our truth and about who we are. And that’s sometimes not very likely to happen in a coffee shop. You may walk around a lot of other humans but there is no heart to heart or there is no emotional connection. 

I think of the CTO at Product Hunt. His name is Andreas Klinger. He had a great suggestion. He said, “I think it’s a good idea for remote workers, wherever they live, to find other remote workers and to start small offices together so they could develop a group cohesion, even though they don’t really work together.” I love that.

Matt: A lot of folks listening to this are probably on one side or another of a one-on-one with a direct report or a manager. So what would be some good questions or things for people to do when they are in those meetings?

Leo: The most important question I think for a manager is to ask the person how they are doing. It’s colloquially so common to answer that with “fine.” 

Matt: It’s almost reflexive. If you said, “How are you doing?” I’d be like, “Yeah, good” or “Fine.” I wouldn’t even think about it really.

Leo: Right. Exactly.

Matt: Because it’s very vulnerable to answer something not — 

Leo: Right. So it becomes a question [of] how can you give people a chance to open up. The number one way I know how to do that is to give space to the other person to resolve things themselves. As a manager, the best thing you can do is train yourself to hold space for yourself so you are not having a million things that you need to unload onto your employee, to keep making more room, to keep letting more things bubble up that can be resolved. How do you feel about this? What do you — To keep it with open-ended questions and to let advice maybe only come in at the very end.

Matt: You cofounded one of the more prominent distributed companies. If you did another company, would you make it distributed again or do you think the in-person is more important?

Leo: I would probably not start distributed. For a sapling to grow I have this feeling that being in the same room together could be really, really vital, at least the first two people. 

Matt: I would actually — I think I would probably agree with that. WordPress, we were always distributed because it was open source. But for Automatic, the early folks, myself and Toni [Schneider], who joined as the CEO a few months after it started, we would see each other quite frequently in San Francisco. I was more based there at the time.

Leo: Right. So I think that early time, being together could be just extremely vital. And over time I think I feel I would be still excited to open that up and to make it fully remote as you go beyond ten people. And I would — remote work is a little bit like the Wild West. It has so many benefits, but there’s so much that’s not understood about the dynamics. 

I would probably be even more conscious about, first and foremost, my own coping strategies to working alone a lot and setting myself up much better. Often times the people that joined later, they were way better set up than people that were wanting to have a job at the company, they already had their families set up, they were happy to spend more time with their kids and at home. Often times they were better set up than me as one of the founders to like — that’s all over the place all the time. 

Matt: Let’s say we are doing a distributed company, we talked about some of the advice you’d have. Any other tips or things that you think from your experience folks in a distributed company, managers or founders, should think about?

Leo: Cultivating human-to-human connections as much as you can within the company. I had this one idea, I think what would be great is to have for these distributed companies in particular, to have a resident stress therapist that people could just go to and sit with for an hour and pour their heart out in relation to what is going on in the company so that they have some context. 

And then to meddle with the less productivity-related things when I believe — productivity is always about emotional states anyways. When we are not productive it’s because the task at hand has some emotional charge that stops us from doing it. You know, we are scared because of how people might receive this. A lot of people are scared of being successful and being seen because there is a lot of underlying trauma around actually being seen for what people do. 

So I think the reason when someone doesn’t want to do a task, there is some underlying emotional charge that’s not being taken care of and finding a way to get to that within a company through maybe a group activity, a regular structured or unstructured time where people can interact with each other, and to work with a manager, or to have a stress therapist or something like that, so that those aspects of your life that are often where you get stuck, they can get unstuck.

Matt: I’ve been asking everyone if you could imagine twenty years in the future, what percentage of jobs do you think are distributed or not in the office?

Leo: I would maybe say thirty percent. 

Matt: Thirty percent. All right, I appreciate it. Well, Leo, thank you again so much for joining me today. A lot of good tips. And you’ve given me a lot to think about.

Leo: Thank you so much for having me on, Matt, it’s been a real pleasure.

Matt: That was Leo Widrich, and you can find him on Twitter @LeoWid, or his personal site, powered by WordPress, leowid.com. If remote work is going to become the rule rather than the exception, we’re going to need to come up with ways to cope emotionally with our new social environments. Maybe it looks like regular team meetups, maybe it’s a hangout in virtual reality, maybe it’s co-working spaces with happy hours. Maybe if people feel less pressure to leave their hometowns to go work at employment hubs, they’d be able to maintain stronger ties with friends and family.

The solution is going to look like all these things and more. Whatever the future of work looks like, I’m glad that people like Leo are thinking about the psychological traps that might be easier to fall into when working from home. I know that the next time I start to feel a little lonely, I might plan to go grab a matcha latte with a friend, so my vagus nerve gets some exercise.

Design leader John Maeda on how to foster creative collaboration on distributed teams

Read more about John Maeda in “Helping Creativity Happen from a Distance.”

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

John Maeda has spent the last three years leading Automattic’s design team, and on this episode of the Distributed podcast, he reflects on what he’s learned with our host, Matt Mullenweg. John shares how to facilitate collaborative creativity across a distributed team, explains why smart managers blog (and vlog) prolifically, and discusses how giving and receiving feedback with a spirit of gratitude, humility, and empathy is essential for managers, especially in a distributed context. 

The full episode transcript is below.


MATT MULLENWEG: What did real-time remote collaboration look like 30 years ago, in the primitive era before Slack and Zoom? My guest on this episode of the Distributed podcast knows, because he was there. 

Designer, author, and Automattician John Maeda spent the latter half of the 90s pioneering a new field called computational design at the MIT Media Lab, a legendary sandbox for researchers who wanted to explore and create the future of tech. Computational design was a bold new approach that applied design principles to the creation of hardware, software, and computer networks, and John helped define it from the beginning.

By 1999, John had developed enough of a reputation for Esquire magazine to name him one of the 21 most important people of the 21st century. Wired magazine once said that “Maeda is to design what Warren Buffett is to finance.” 

My company, Automattic, has been lucky to have John working with us for the last few years, and he will be moving to Publicis soon. He’s been leading a team of 70 designers scattered all over the world, and before he left, I wanted to talk to him about what that’s like, so I’m thrilled that he’s able to join me for a discussion about creative collaboration at a distance. 

We are here today with John Maeda, who leads what might be the largest all-distributed design teams, or at least that we know of. He is the author of three books, The Laws of Simplicity, which is actually what introduced me to John’s work, Creative Code, and Redesigning Leadership. And I believe there is a fourth book on the way, is that correct?

JOHN MAEDA: There is. It’s How To Speak Machine. And thanks for having me on.

MATT: Oh, no problem. So your title is Global Head of Computational Design & Inclusion.

JOHN: Mhm, mhm.

MATT: Computational design might be a concept that not that many people are familiar with as well. Tell us about that.

JOHN: Well actually, people ask me about that. That’s why I thought that How To Speak Machine is the first primer on that because when we think about the value of design right now, because of the technologies we use today, it isn’t a picture, it isn’t a clever drawing. If it’s computational, if it’s driven by code, or it’s tied to code, it can achieve scale, it can achieve behavior, it can be interactive. 

If you think of an early computational design system, that would be WordPress. It’s interactive, I can use it as a tool, it’s not like a poster in the MoMA collection, but it’s a usable system that is running with computation. It never gets tired. Want to add a post again? Okay. Want to add another post? Okay. 

So the computational system never gets tired. Whereas we’re in a room with a beautiful wooden table. This table, if we — we wouldn’t want to hurt this table, we don’t own this table, I know — but if we kept hitting at it, it would eventually fracture. It has physical laws. But computational systems behave differently because they are built out of programs.

MATT: Where do humans fit into this?

JOHN: Originally humans and computers interacted, like Hiroshi Ishii’s human-computer interface world.

MATT: Yeah.

JOHN: But now computers and computers interact, as you well know. They’re hanging out together without us, especially with AI. They’re hanging out. Like, “What do you got?” “I got this” or “I got that” “Well give me some of that.” So — 

MATT: I love the concept of the AIs that train against themselves. 

JOHN: Oh those are really cool.

MATT: Like the Alpha Go, [or] the other things where they have this adversarial learning against itself. So it can play hundreds of millions of games in a day.

JOHN: That concept you described used to be science fiction but now, because of the resources we have available to us by the cloud or everything we can buy now, that’s a normal thing. If our raw material has changed then design should have changed too vis-a-vis computer-based systems.

MATT: And has it?

JOHN: It’s trying to. That’s the one thing I’ve realized is so hard — this is across the tech ecosystem — is that there are a lot of designers who came from the past. And so when we look in this room, the person who designed the texture on that wall over there, that’s a kind of design, but it’s less relevant to the design of a new release of a new feature that needs something that actually has to ship right now. 

And the distance between that design and a design that once it’s shipped now has to iterate and improve at a rapid velocity — that’s a different kind of design. I think most of the design, maybe over 90%, is stuck in the old design, not in computational design. So that’s why I wanted to highlight that when I joined your merry band. 

MATT: Let’s say someone is listening to this, a younger person who is not currently in design and wants to go into it, and wants to be in this kind of present or future you’re describing. What should they work on?

JOHN: They should use WordPress. [laughter]

MATT: Okay, so that’s a good start.

JOHN: No, no actually not in that way. I have been using WordPress intensely, over two years now, getting on three, and it has really reminded me how the internet works. It has exposed the messiness of how information is transmitted, how it’s displayed on multiple platforms. 

It’s like people who really love WordPress will hate hearing this but it’s kind of like infants, for them to walk, there is this baby walker thing, I’m not sure if it’s legal anymore, but there’s this thing where the baby can stand up in this walker thing and they can move, they can move around the room and it’s like, “Wow the baby is moving around.”

MATT: It’s like a little circular thing with wheels?

JOHN: A circular thing with wheels on the bottom, exactly.

MATT: I haven’t seen one of those recently but I know what you’re talking about. 

JOHN: They must be illegal now for some dangerous reason. But to me it’s been like a baby walker because — I know a lot of the high tech stuff but I lost sense of the basics in many ways. 

MATT: What are some of those basics that people should be familiar with?

JOHN: The basics are, first of all, collaboration.

MATT: That’s not a basic. That’s hard!

JOHN: Well I mean that’s a basic that comes — if you build software yourself you don’t have to collaborate, right? But by having a distributed system you have to collaborate. So just to get in touch with that, that’s been great.

MATT: What makes you good at collaboration?

JOHN: Listening. I think it’s the number one important thing is listening. What is the saying, two ears, one mouth? So two-to-one? [laughs] 

MATT: But everyone can’t do that at the same time.

JOHN: Oh yeah. 

MATT: Sometimes it’s going to be impossible?

JOHN: Yeah. The collaboration thing is key, the listening part. The second thing is being technically facile. Being able to write poetry in code. I think for a long time, because I was in the classical design world where coding is bad, like coming back into, via Kleiner Perkins and eBay and Automattic, I’m like, “Oh, coding is good.” And why is it good? It’s because you have agency. What does “creative” mean? It means I’m creating. And if you can code you can do so many things. 

So collaboration is important and to be able to make code is great. The thing I love is how I think of what I’ve learned with WordPress — it’s like Lego. And people will say, “Oh it’s just Lego, it’s not like real wood, real marble, real concrete, it’s just Lego.” But in this world of having an idea, an MVP or an MLVP, you want Lego to be able to make ideas spun up quickly. 

MATT: You brought it full circle. You said community-made platforms win or lose. Some people say that WordPress is not the best CMS, but it does have one of the largest communities and has been the most successful.

JOHN: Yeah.

MATT: You also said that the first thing that designers need to know is collaboration. 

JOHN: Yes.

MATT: So it came to people.

JOHN: Yeah.

MATT: As we said in the intro, you lead definitely one of the larger all-distributed design teams. So if collaboration is important for design and you can’t have everyone in the same room around a whiteboard, what do you do? What are the challenges? And what are some of the benefits?

JOHN: You just reminded me how in the early 2000s or late ’90s I had made this system called Design By Numbers, and it was a system to teach anyone how to code. It was very limited. You could only draw in a 100 by 100 square in black and white. Super constrained system, super easy to teach anyone computation. And then two people on the research team, Casey Reas and Ben Fry, who were involved with this system, said, “I think this system should be less constrained. It should be color. And why is it limited to 100 by 100?” 

And so they built this system called Processing and they did two things. The first is they built a community center portal around it and the second thing they did was they open-sourced it. And at the time I’m like, “That’s never going to take off. That’s just sort of a — what is this? It’s never going to happen. You should be working on something else.” And that’s why I never really believe anything I say because I could be wrong. I was so glad they didn’t listen to me and they went off and made this Processing thing. And I think there’s a gazillion books about it, there’s communities around it.

MATT: It’s extremely popular, yes.

JOHN: I had to learn from them the power of community because I spent most of my career making software by myself. Everything I made by myself, I designed every book by myself because that’s what I thought people did. The great creators made things by themselves.

MATT: Which is also amazing because, as you know, so many great artists had workshops, architects…

JOHN:  I know, I didn’t know that. I didn’t know that Michelangelo didn’t paint all those. 

MATT: Leonardo da Vinci… 

JOHN: I didn’t know that.

MATT: Raphael. Yeah.

JOHN: Well, you know, I grew up with —  

MATT: Today, Jeff Koons.

JOHN: — my family had no education, we had no books, there wasn’t internet, I had no idea.

MATT: The myth of a solo creator might be one of the most corrosive to creativity in general actually.

JOHN: Ohh totally. Oh my gosh. I almost died doing that. I got sick, overworked, I was in the hospital for three weeks. I went over the line, you know?

MATT: You told me about that before to caution me against it.

JOHN: Oh yeah, it happens, it happens. It goes past… 

MATT: I appreciate those cautionary tales. It’s worth noting on this podcast itself is not a solo endeavor.  

JOHN: I agree 100% and I think that the solo creator myth is something that I strive to break through sharing my own embarrassing failures around this. And then when working with teams the number one important thing that I found is respect.

MATT: In working together over these past few years you seem to exhibit an incredible amount of empathy, which is also important for design. Maybe we’ll add that to the list. Or I’ll put it on my list, you don’t have to put it on yours. How do you balance that empathy with that, [so you’re] able to get through these tough things?

JOHN: One of my favorite artworks I’ve made in my life — I don’t have many things I like that I did, but I was in a meeting at MIT where I was having this feeling of, “Whoa, this is feeling really ugh, you know?” I calligraphed on a piece of paper “thicker skin” 75 times. And it’s entitled “Thicker Skin 75 Times.” And it was sold at an auction for charity for UNICEF in Paris. But it’s my proudest piece of artwork because all of my feeling went into that simple drawing to remind myself that it really isn’t about them, it’s about me: Can I have thicker skin?

MATT: It’s a powerful concept.

JOHN: Yes. But it hurts still. It hurts. If there is someone that you really respect and doesn’t respect you, sometimes it works, sometimes it doesn’t. Does it hurt? Of course. Every time it hurts. Like, “Oh wow.” You let someone down and you don’t forget it.

MATT: But does that close you off to the full range of human emotions?

JOHN: That’s more a combination of thicker skin and gratitude.

MATT: Gratitude, okay, that’s one we haven’t talked about yet.

JOHN: Yes, thicker skin is there if you’re feeling bad and then the gratitude is there because it’s like, “This is an awesome world, like, this is so amazing.” Or you’ll feel gratitude for someone in your past and that activates something good in you. I always think about how I would not be where I am today if it wasn’t for my 11th grade high school chemistry teacher, Mr. Wakefield, who took an interest in me as being the number two smart kid in his class. 

The number one kid was so much smarter but came from a really good background whereas I came from a background where I knew nothing. My parents had no education, we didn’t know what the future should be like. I was working after school at my parents’ shop, on the weekends. I hated summers because I had to work there all the time. And so Mr. Wakefield said to me, “You want to go to a good school, you’ve got to have stuff on your application that makes you credible.”

MATT: The extracurriculars?

JOHN: And I was like, “What’s that?” So he said, “We’ll make a science club,” and whatever, so we did that. And then he said, “You need to take a class at the local university over the summer.” And I said, “Oh my parents won’t let me do that because I have to work at the store.” And then Mr. Wakefield came to the store on Saturday, on the weekend, to talk to my parents. 

MATT: Wow.

JOHN: He didn’t have to do that. He was a retired Boeing engineer, he never would venture into the Chinatown area. I mean he didn’t quite fit the whole thing. [laughs] He came and talked to my parents and said, “You want your son to go to a great university, let him take the summer off and do this, give it to him.” And they did. 

MATT: And they did. What did you study that summer?

JOHN: Organic chemistry. I loved chemistry. I was going to become a chemist. I was almost going to be — at MIT the only class I didn’t fail out of in the first year — it was a really bad year — was solid state chemistry. I got one of these rainbow stickers on my tests. Oh it’s the one moment of “Ohh, I’m not an imposter. Should I be here?” I got the golden sticker that one time.

I think of Mr. Wakefield, I think of other people like that who gave me a chance and I feel gratitude towards them. And then it gets easy, like how can I serve you, how can I help you? It’s easier.

MATT: One area we didn’t fully cover was that chemistry for teams or the collaboration for design teams. In a remote setting does anything stand out?

JOHN: Oh my gosh, so this is all about distributed collaboration so I know — exchanges around commentary on code and ASCII text, etcetera, some images, some pull request is initiated, it goes through the shipping — I think of GitHub or GitLab or any of these systems, like a big ship construction site where the ship is going through this gigantic tunnel about to launch out there.

For developers it is highly developed but for designers it’s not developed. That’s why I think things like Figma are so popular because they closely emulate high-network collaborative spaces that remove the abstraction between storage and actual application. [It’s] super reliable, it runs fast and is social to the extent that it’s not actually annoying like Slack can be sometimes. [laughs]

MATT: Why can Slack be annoying?

JOHN: Slack? Oh my gosh. Slack can be annoying for so many reasons. And some people say to me, oh well you’re not Gen Z or Millennial so you don’t get it. I’m sorry, but I think I have been able to Slack with the best of them. 

MATT: I’d say you’re a pretty big Slacker.

JOHN: I know, I try. I try to be a good Slacker. But the feeling I have around a system like Slack is that it moves things so quickly that you can’t think fast enough. And a quanta is so small, the message size is so small. And if the organization is a six-person start up — I think Slack is fantastic, but anything larger — it isn’t about the message, it’s about the feeling. Like, how are you feeling for yourself as a leader of all these people? You need to get a sense of how they feel. And from a Slack instance you can’t get that sense of feeling unless someone is really good at choosing the right emoji, you have no idea, is this the real reaction? You can’t tell. 

MATT: I know creative work — I think creative work requires uninterrupted periods of time, of focus.

JOHN: That’s a good hypothesis. I think you’re right. Yes, you’re right because one of my favorite metaphors is by the late Gordon MacKenzie, and it’s about how he draws a graph — a graph across the — a horizontal line, and then the majority of the line is called “making milk time,” and the end point of the line is “expressing the milk.” 

So a cow is sitting there eating, and you’re like, “Come on, cow, give me milk. Give me milk, cow, give me milk.” And then, “Where’s the milk, cow?” And the cow is just sitting there, chewing the grass. And it’s like, “This cow is not working.” But actually the cow is making the milk but the cow is only rewarded when they express the milk. The example is about how creative work takes eating-grass time and sitting in the sun, otherwise all you get is barely made milk.

MATT: And you’re leading 75-80 people around the world, 24/7. 

JOHN: Mhm.

MATT: How do you find that making-milk time?

JOHN: Because we’re distributed and because we have all kinds of teams that work with designers, I think it’s up to the local zone of leadership to be able to create that time. The best that I can do is a round robin, asking, “What’s up, what are you doing, what are you doing outside of work?” And then someone will say to me, “But that’s not work.” And I’ll say, “It’s your work as a creative person to express yourself.”

So one thing I’m really happy about is our blog, Automatic.design. You may remember in the beginning it was hard to get off the ground because some designers felt like, “Well why am I going to blog? What is the point of blogging? What’s that for?” And my point is blogging is good for you. It’s mental health, it’s expression, it’s sharing your process with the world. And when you relate to the world, your standard of quality floats to that value of the world. It’s a market economy of ideas and by putting ourselves out there, you become relevant.

MATT: I’ve noticed, talking about that low-bandwidth communication of text, downsize to Slack.

JOHN: Yeah.

MATT: You internally and now externally are on your YouTube channel.

JOHN: I’m doing YouTube, I’m a YouTuber now. Oh my gosh, I love it.

MATT: Yeah, you create a lot of these videos.

JOHN: I do. 

MATT: And I also perceive that you’ve literally created a lot of videos. You edit a lot, you insert emojis.

JOHN: I make the whole — It is the classical “I make it by myself thank you very much.” [laughs] 

MATT: Yes, so why are you using video to communicate? 

JOHN: Oh my gosh.

MATT: Internally as well. We have so many different tools.

JOHN: Look at you. You’re a WordPress-world person, you’re speaking into a metal thing, holding it with your hand, you’re not typing, you’re audio casting. So you see the diversity of the ecosystem. So YouTube to me represents really what the younger generation has figured out, is [it’s] so much more convenient.

MATT: Should managers at distributed companies or leaders learn video editing?

JOHN: A thousand, thousand percent yes. Because editing skills are ways to communicate in the same way that blogging is, but be careful to add a closed-caption, subtitled track because that makes it even more inclusive for those who have problems understanding spoken English, or for a language barrier.

MATT: One thing that’s cool, and actually one of the features I’m most excited about, is just launching. Our internal video player just launched — 

JOHN: Oh yeah, congrats, yeah that was good.

MATT:  — the speed thing.

JOHN: That’s important.

MATT: Which YouTube has had forever. So you can speed things up or slow them down.

JOHN: Yes.

MATT: I’ve found it’s interesting for meetings. What might be a synchronous status meeting that might take 15 minutes  —

JOHN: Yeah, you could  

MATT: You can get through in ten minutes or eight minutes depending on your speed of processing.

JOHN: Whoa. You can express it.

MATT: Especially people who listen to the podcast, I imagine more than half, if not more, are listening to this sped up right now.

JOHN: That is wild.

MATT: So you actually train yourselves to be able to listen faster. 

JOHN: Oh that’s so interesting.

MATT: And I wonder if I can improve efficiency.

JOHN: Well one thing I’m doing with the team around me is my direct reports, on Monday, and you don’t know this, but Monday what we do is I have a one-minute video requirement. On Monday you post your one-minute video and that’s your stand-up, but it’s async. And that way you can comment on the video. Any extra comment can happen by text. But you can also hear it in full fidelity how someone is experiencing their life and their work.

MATT: That’s really interesting.

JOHN: It’s an async stand-up.

MATT: What are some other things you do in leading the team? I know you have a Monday, Tuesday, Wednesday publishing schedule.

JOHN: Yes I do, yes.

MATT: Tell us about that and more. 

JOHN: Okay. One thing I’m really excited about is learning the distributed universe and how hard it is to have a point of reference. If you work at a physical place, you walk in, you can tell the seasons, there is a Monday, there is a Friday. Monday feels so different than a Friday on-prem. So you lose your sense of gravity. There is that Sandra Bullock film — was it Gravity? Where she’s floating in outer space and it’s “Which way is up, which way is down?”

So one thing that I developed after a lot of feedback — I love feedback — every negative or positive feedback I’ll share internally, just with everyone, because it’s easier that way. If people want to talk about me, they have already talked about me because I’ve shared it and it’s easy. But one of the feedback points I got was that I was posting or sharing too much information. And then I realized, well maybe it’s because I haven’t given it structure. So I gave it structure. 

But then I realized that structure isn’t as good as time structure. Because time creates gravity in a distributed organization. So Monday’s post is about the external world, the external realities, Tuesday’s post is about business, and Wednesday’s post is about organization. And I limit myself to posting in that cadence. People expect Monday to be a certain thing, Tuesday, Wednesday. 

The other practice I developed in the team around me is I borrowed a technique developed by Joel Califa, he’s a designer I used to mentor, but now these people who I mentored are like my teacher[s]. It’s a spreadsheet where everyone posts what they’re going to do that week and then they rate how that goal has been achieved during the week. It’s like an old-style Japanese office-memo thing. And the reason I use a Google Sheet and not a special tool is because everyone authenticates. There’s no “Hey can I get a login, can I get a login?”

MATT: Yeah. At our company everyone has a Google account.

JOHN: Yeah, and that Sheet is open to everyone in the company too. I love the idea of transparency that you brought into the Automattic culture or created with your team members over these years. And I think transparency is so important but clarity also is key.

MATT: You said that you love feedback. Positive, negative, you love sharing it.

JOHN: Yes, I do. It’s good.

MATT: What do you think engenders a healthy culture? Does everyone on your team take that same approach? And how do you judge a healthy culture of feedback?

JOHN: I’m laughing because the best feedback is delivered non-anonymously.

MATT: I know you feel very strongly about that.

JOHN: For me I feel strongly about this because when you deliver it non-anonymously you can understand it better. I have two favorite sayings and they’re too long so I can’t memorize them. But one of them is by Coach Pat Summitt, and paraphrasing, “When you’re able to give someone straight feedback you’re showing them the compliment that they will be able to take it.” 

And so when people give me feedback, does it sting that I am no good at something? Yes. I’m like whoa, I thought I was good at that. And I might think they’re wrong. But then when they say how I didn’t achieve something I’m like, “No, you’re right, I could improve there.” If you get it anonymously you don’t know the smell or taste of it. It’s like if I gave you —  

MATT: It’s missing context, for sure, yeah.

JOHN: It’s missing — You have to fill in the rest of the story 80 percent.

MATT: It also seems you can’t get any anonymous follow-up on it?

JOHN: Well you can tell everyone “I got anonymous feedback, this is what I’m doing.” And then you give more power to anonymous people and those who actually give you the — 

MATT: But you share all the feedback, anonymous or not, right?

JOHN: I do, yes. And one of my proudest achievements is the anonymous feedback and the in-name feedback is just as bad. [laughter] 

MATT: So people are comfortable saying it either way.

JOHN: Right, right. 

MATT: You also work a lot on inclusion.

JOHN: Mhm.

MATT: That’s from a position of privilege as well.

JOHN: Absolutely and I —  

MATT: You’re very powerful and you’re John Maeda. 

JOHN: People think that I’m something. An octopus, like, whatever. But that’s why a lot of what I do is reiterate that I’m only as good as what I do now.

MATT: How do you make people who might feel that they don’t have that privilege to give things to you directly, how do you make them comfortable with that? 

JOHN: I haven’t cracked that one yet but it’s on my list of… how do I invite them into the fact that my only goal is to serve others and I cannot do that unless — think of all the user research. Unless I have high-fidelity user research, how am I going to improve? Maybe my goal is to center on that concept with more people that I do believe in agile development, I’m a computational system, organic, [laughter] and how am I going to iterate and improve if I don’t get really high-fidelity feedback? 

Maybe I might become much more open to delegation of that. Because there are some people who feel that I’m in a privileged position and some people feel privileged enough to go straight with me. Like if you don’t feel comfortable with me, talk to them and I could just anoint that role —  

MATT: But then you lose the fidelity.

JOHN: I do. And then I also do recognize that there are those who will always feel something. And it’s often not about me, it’s someone like me that in their past [with whom] they had a bad experience. So I totally understand why there would be no reason that they feel that they could be candid with me, because something bad happened in the past.

MATT: Are you also that candid with everyone you work with?

JOHN: Am I that candid? It depends. 

MATT: Can everyone handle that kind of raw — 

JOHN: That’s the challenge of getting older for me. When I was younger, I would tell everyone everything I thought. Oh my gosh, people couldn’t stand me, for good reason. I mean it was okay, I forgive them. Actually I hope that they forgive me. I would just tell them what I think and I was direct all the time. 

And then I realized wow, this is not working. This is not working. I believe in the “I’ll show you respect by telling you what I think.” But it’s like, “No, actually he doesn’t want to hear what I had to say. Whoops.” So I changed. 

MATT: Why is it bad if people are doing the same to you, not giving you the direct feedback?

JOHN: With people who I develop a strong working relationship with, then they are the ones who ask me, “Can I get your feedback.”

MATT: So conversely they feel more comfortable with the raw feedback from you?

JOHN: Yeah. And some instances, some people want that, some people can, quote, “handle it,” which means that they were privileged in some way where that became — where that’s doable. But there are some who just had a really difficult life that they just don’t want to handle that and it just hurts them in a way, it doesn’t help them. And so I’ve become much more conscious of “Huh, how do I adapt to what you need?”

MATT: In design you are also overseeing everything that goes out to all of our users.

JOHN: Mhm.

MATT: Everything we’ve been saying about feedback is pretty universal. Is there anything specific to distributed [work] that you want to throw in there? 

JOHN: In a distributed organization I think that the value of it is that you can now control your life differently. I know so many people [for whom] distributed work has been able to make them better parents, better children to their parents as caregivers. Them coming from that point of view is the beginning of recognizing that this is an amazing job to have. And do you enjoy that aspect of those jobs? Yes. Great. Now what kind of work are we doing and how can we safeguard that wonderful thing that you are able to do because of this paradigm. 

That’s what interests me the most, is that it’s a really special thing to be able to work distributed, and if you can start from the respect of that versus the wonder of it, then you have hard conversations about, “Now what should we do with the work to safeguard that?”

MATT: Tell me about your ideal work space.

JOHN: My ideal work space — I’m still QWERTY, we’re talking typewriter-speak. How do you say the other one?

MATT: Dvorak?

JOHN: Thank you. I don’t know how to pronounce it. Dvorak. I love a Kinesis keyboard because it has helped me I think —  

MATT: Those are the curved ones, right?

JOHN: It’s the curved one. In my late twenties I had really bad RSI. It’s the way I hold my body, but that really helps. I like to have that nearby. I like it super quiet. I don’t like to put headphones on, it’s a bit constraining.

MATT: Do you put music on?

JOHN: No music, no music, but hopefully art around to distract me.

MATT: Besides the Kinesis, any must-have equipment? I think you use a custom camera, right?

JOHN: Oh my gosh, I have fallen in love with this new thing. You know how headset experimentation is so important for distributed? It’s almost like a hairstyle problem. I found that in-ear musician-quality microphone monitor headphones, they’re great because they —  

MATT: Did you do the custom?

JOHN: There is this memory tip cushion thing that you can get that is super comfortable, sound-isolating. For audio quality it’s fantastic. 

MATT: That’s amazing.

JOHN: I love good microphones. Podcast-quality microphones, the sound quality is so much better. I do love the Sennheiser headset for sound-isolation quality. Like, we can be talking and I’d be in the airport, and you’re like, I don’t hear anything.

MATT: Oh yeah. 

JOHN: That’s bizarre how well that works.

MATT: Noise-cancelling not for you ears, for the mic. A noise-cancelling mic.

JOHN: That’s bizarre how good that is. But I do always feel a little embarrassed wearing it. You have no problem being in a restaurant wearing it. [laughter]

MATT: No, you look like you’re in a call center or something.

JOHN: I can’t go there. You wear it all the — I can’t do that. Yeah.

MATT: Zoom, Hangouts, Skype? What’s your go-to?

JOHN: Oh my gosh I can’t stand all of them. I like audio-only if I can. I like phone, yeah. 

MATT: Hmm. So you make phone calls?

JOHN: I make phone calls, yeah. It feels good. 

MATT: What’s your number-one tip for getting things done?

JOHN: Is if you’re lucky to have a good assistant, and if you are less lucky, having any good to-do note system, they always work. So the competency of making a list, oh, so good.

MATT: One thing I love about working with you is you’re go, go, go. 

JOHN: Aww.

MATT: What is your drive there?

JOHN: My parents worked so hard all their lives. I think about my father. He’s 84 years old, he’s hunched over, he can’t stand up straight, because he was carrying so many heavy things all his life. My mother, because of the cold water involved in tofu — her hands — she can’t feel anything. They worked extraordinarily hard. They are an example that was set that tells me I should do more. 

MATT: What are some of your habits that contribute to that, good and bad habits?

JOHN: I’m not good at vacationing. As you know, it’s not my forte. 

MATT: That was a goal for the year. 

JOHN: You gave me feedback and I took it, and I was like, “Okay, I’ll do this vacation thing.”

MATT: Although I think you worked the whole time.

JOHN: I had to get stuff done. [laughter] But vacation, not good at. I don’t read enough. You read a lot. You’re always reading. I don’t read enough.

MATT: You probably read all day. Do you mean books?

JOHN: Books, books. I’m consuming information. But I want to get good at reading books.

MATT: And finally, 20 years from now, what percentage of jobs do you think will be distributed?

JOHN: I think for developers, I think it will become a norm. I think for whatever we think of for designers it will be 50/50. Fifty for designers who are doing much more of the traditional creative, emotional type of work that requires more high-bandwidth collaboration, but it’s going to be expensive, that work. But the other half is all going to be computational.

MATT: Well, thank you so much, John.

JOHN: Thank you. This was fun.

MATT: That was John Maeda. You can follow him on Twitter at @johnmaeda. That’s J-O-H-N M-A-E-D-A. 

Slack is a tool that’s so widely used it feels ubiquitous in the tech world. And when everyone uses a tool, sometimes it can be difficult to imagine how it might be improved, or how a different tool might be better. It’s a privilege to hear someone like John Maeda — someone who has spent much of his long career thinking about digital interfaces — dissect the technology and talk about the way that it works, and where it falls short.

Hearing about the live-video-chat-meets-virtual-whiteboard tool John helped create in the 90s makes me think about how distributed design teams might use that today. It’s a great reminder that devices and interfaces can always be iterated on, which is both a great lesson from computational design and one of the great pleasures of building digital tools.

John has a humble, thoughtful approach to distributed collaboration, and thinks about how humans operate as much as how computers do. When you’re working with people across the globe, sometimes the best collaborative tools are the oldest, like listening, gratitude, and empathy. 

John’s time with Automattic will be coming to a close soon — he’s accepted an exciting new role with consulting firm Publicis Sapient — but I hope that his thoughtful and humble approach to distributed collaboration will live on in our design team, and I look forward to him contributing to Automattic as an adviser.

Next time on the Distributed podcast, we’ll be talking with Leo Widrich. Leo helped build a successful distributed startup called Buffer, and was living the Bay Area dream. But he felt something was missing from his life, so he quit his job and turned to ancient wisdom and mindfulness to achieve emotional resilience. We’ll hear Leo’s story, and learn how distributed workers can avoid the psychological pitfalls that are unique to working remotely.

Thanks for joining us. 

Upwork’s Zoe Harte and Han Yuan on Managing People and Products in a Distributed Company

Read more about Zoe Harte in “How to do HR in a Blended Company” and about Han Yuan in “Engineering with Empathy.”

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

On today’s episode, two leaders at Upwork share how they do distributed. First up is Zoe Harte, Upwork’s Head of Human Resources and Talent Innovation, who speaks about her experience of overseeing a blended team of full-time and freelance employees. Then, I talk to Han Yuan, Upwork’s Senior VP of Engineering, who shares insights on the “soft” skills engineers need to work effectively in a distributed world.

The full episode transcript is below.


MATT MULLENWEG: Back in June we had the pleasure of speaking with Stephane Kasriel, the CEO of Upwork, the world’s largest freelance marketplace. Stephane laid out a compelling case for the distributed model as a way for talent-starved companies in expensive, crowded cities to do business with workers who live in places with comparatively sluggish economies.

But Upwork’s not just thinking about this in theoretical terms: they practice what they preach, with a distributed workforce of their own. In this episode, we’ll talk to two Upwork employees from two very different practice areas who give us glimpses of how their company does distributed. 

First up is Zoe Harte, Upwork’s Head of Human Resources and Talent Innovation. Upwork’s legal, finance, and even HR departments are a blended mix of full-time and freelance employees scattered across dozens of countries and cultures. Zoe helped to grow the company’s workforce by 75 percent over the last six years, giving her a world-class perspective on how to expand and maintain fluid, flexible teams. 

After a great conversation with Zoe, I speak with Han Yuan, Upwork’s Senior VP of Engineering. Han gives us an inside look at how his team’s diversity of culture and thought becomes a powerful asset. He says this diversity fosters curiosity and allows the company to tap into a wide array of perspectives and experiences. 

OK, let’s get started with Zoe Harte. 

ZOE HARTE: My name is Zoe Harte. I look after human resources and talent innovation here at Upwork. I’ve been here six years now. I started when we were oDesk, prior to the merger of Elance and oDesk, and have seen everything transform. I’ve been doing HR for almost 20 years at this point.

MATT: Wow.

ZOE: Yes. And I spent almost a decade at Yahoo.

MATT: Tell me a little bit about your HR team. 

ZOE: There’s the traditional side of the house, which is — we have recruiting, we have the HR business partners.

MATT: How many people?

ZOE: We’re about 20 in that world. And then we have — there is another group of people who help do the onboarding for the talent innovation team — is what we call the freelancers, who work directly for us, and they help them with the onboarding, getting access to the Upwork systems in a compliant fashion and provisioning them, making sure their business documents and all of that are done in an appropriate way.

There are also people in our organization who partner with freelancers, who are working for our enterprise clients to help make sure that they are onboarded successfully onto the platform, getting access to those companies’ data or whatever it is that they need. That’s where making sure all the documentation, the independent business license and all those things are done. So it’s pretty varied in terms of what HR encompasses for us.

MATT: So about 20 for the full-time?

ZOE: Mhm.

MATT: So 450 full-time Upworkers. 

ZOE: Yup.

MATT: About how many for that broader talent group?

ZOE: That’s about four.

MATT: Oh, so that’s pretty leveraged.

ZOE: It’s really leveraged. Yes. They would like to have a little more help there. But we also then use freelancers ourselves back to supplement the team too. Our team — 

MATT: What sort of things do you use freelancers for in HR?

ZOE: For everything. We use freelancers to help us design learning programs. We’re moving some of our compensation to a different philosophy. We worked with a freelancer to do a video explaining the why and the how that impacts everybody. We work with freelancers when we’re looking to bring in different skills or scale in our organization. 

So for example, when we were building out our Chicago presence and we were hiring a lot of sales people, we needed to do a big hiring push all at once. I knew we didn’t need a ton of recruiters full-time focused on that, but we needed a lot of sources to really dig deep into the talent network within Chicago. And so we did that with bringing people on in the platform. So that’s just a scale issue. And then for skills, like video design. I can’t do that. But this person made this video that’s amazing, and it makes it a complex thing that’s coming out of our department easily digestible and clear.

MATT: I definitely live in the distributed work world and until you started talking about that I had never thought about parts of HR being something that could be freelance.

ZOE: It all can. And that’s one of the things that is so great about how Stephane has set us up here, is that the expectation is every single organization within Upwork is a blended organization that relies on freelancers as well as full-time employees. So legal, finance, all of us, even the organizations that you’d be like, “That’s hard,” there’s always additional stuff that can be done.

MATT: Yeah. And the third bucket you talked about was enterprise. You might need to define enterprise just quickly.

ZOE: Mm, sorry.

MATT: And what that means in your business and then how many people work on that.

ZOE: So for our enterprise business, that is out of our sales function and so that’s working with our largest accounts. So the biggest companies with whom we work, Fortune 500 and Fortune 50. 

MATT: So I might come to you say “Hey I need 1000 folks to do X, Y, Z.”

ZOE: Precisely. I need to translate these medical documents.

MATT: “And I want you to manage it for me.”

ZOE: So we do both. We have some where it is “I want you to give me just the output, you figure out how to do it,” and then we have others where they are more involved in the guidance themselves and so they’ll say for the marketing organization “We want a design initiative that’s X, Y, and Z and we’ll do it this way.” So Microsoft is a shining example of a company that’s partnered really extensively with us and knows how to utilize freelancers in a wide variety of projects.

MATT: Are there other big clients you can talk about like that?

ZOE: Companies like Dropbox and Pinterest are using us for a variety of different things as well. And then most of the bigger companies — we’ve got GE and other people like that — who are really digging in within different functions organizationally, be it marketing or some of the writing organization, or particularly web design. And the technology pieces — obviously a lot of engineers can really be scaled. We do that here, I’m sure.

MATT: HR is so critical to being a distributed company. How should companies be thinking about this if they’re starting to hire? Let’s say right now I have all my people in one office in Houston, Texas, and now I want to start to engage and hire people in other places, what do I need to think about?

ZOE: You need to think about a lot of things, like, “Is this going to be — I’m going to do this for one set of expansion, so I’m going to go to these three additional states and then I know that’s going to be pretty steady for X period of time.” If that’s the case then I would argue, depending on how many people it is, it may be worth setting up [a] nexus in those places and so then you’re beholden to pay the taxes there and set up all those legal and financial things that you need to do. 

If not and you’re interested in saying “I’m going to need three people in this place for the next three months and then I want to explore the opportunity to have local translators in Brazil for X, Y and Z reasons,” then I think you may benefit by exploring a freelance relationship with those people where you can dial it up or dial it down. 

And it allows both parties to really engage in a way that’s very clear and communicative about [how] these are the objectives of why we’re doing it this way, communication and transparency in terms of what the goals are, the deadlines, etcetera. But you’re not then in a place where you need to manage all the tax implications and all the financial and all the legal ramifications of setting up businesses in a myriad of different countries, which can be hugely taxing, pardon the pun. But in terms of what you need to do organizationally, it can be such a distraction and so much overhead that arguably freelancers in that way can be much more efficient for a business.

MATT: [Are] there ways to manage some of this complexity? Because even in the U.S. you have different worker’s comp laws, you have different tax rates, you have so much stuff.

ZOE: You do. Firstly I would say, have a really good tax person that you can use as a resource, whether that’s somebody you contract with or otherwise. You can, obviously if you’re doing it the freelance way — I would be wrong to not say Upwork will do a lot of this for you, right? We can help with a lot of that. 

But I think in general it’s about being mindful and intentional about it. I think sometimes what happens is we fall in love with a person and a candidate and we think this person is perfect and you’ve already made some kind of oral commitment to them, like “I really want you to work with us on X, Y project,” and then you’re like, “Oh, but man, they’re in Massachusetts and the taxes in Massachusetts are a nightmare.” Or it’s whichever state it is where you realize, “Oh, one of our biggest customers is there and if we set up a nexus there, then we may have to look at our taxes differently because they’re also there. So what do we trigger for both our customers and for ourselves?”

So I think the biggest advantage you have — we have some great tax people here and it really helps us. And we have been very intentional about the places that we have full-time employees versus the places where we’re open to partnering with freelancers — which is worldwide, versus the places where we’ll engage with leased employees — because that makes it a lot easier for us.

MATT: And had you been at a distributed organization before?

ZOE: Personally I’ve always had a distributed team so I never have worked with a team that was solely in one place. And it’s funny, I hadn’t actually reflected and made that connection that I had never done it until I was thinking about talking with you about it. But I have always had that.

MATT: People probably think of a Yahoo as being almost famously all in one place.

ZOE: Well now, yes.

MATT: Help people understand how maybe that org was really large and… 

ZOE: It was. It was sort of ginormous. I was there from ’99 to 2008. And so the company was about 14,000 at its biggest during that time, but certainly grew and contracted at various times.

MATT: That’s a wild time to be at Yahoo, by the way.

ZOE: You know what, I can’t say enough good things about it. We had various offices. So there was a large campus in Sunnyvale but there [were] also offices — we moved our customer service organization up to Hillsboro, Oregon. We had Broadcast.com, Mark Cuban’s thing, in Dallas. We were in LA and New York as well, and then of course all over the world there were Yahoo offices.

So even when I was just managing one person as an HR manager, she was based in Oregon, I was based in California. The other thing, towards the end of my time there, when I had left HR for a while, I was looking after the international customer care organization, and that was in 20 plus countries.

MATT: Wow, how many people was that?

ZOE: That was about 300 people at that time.

MATT: Wow.

ZOE: That was a really great learning opportunity and it also makes you mindful of time zones and different customs and different expectations about availability and responses over the weekend, or what it all looks like and how different it is in different places. 

MATT: In the taxonomy of distributed versus all being in the same room, I guess I would call Yahoo or companies like that as multi-office.

ZOE: Precisely.

MATT: There’s offices all over the world, across all time zones. People would go into that office the majority of the time and — 

ZOE: Yes, there was a lot less actual remote work. Like I’m in my home, you’re in your home, somebody’s in a co-working space. 

MATT: So we just built a time machine. You can go back 20 years and talk to Zoe in 1999 at Yahoo.

ZOE: I know, she could be on it.

MATT: What would you tell her about what you’ve learned at Upwork, a massively distributed organization, that you think would help maybe someone listening to this who is in a multi-office type place?

ZOE: I think being precise and intentional about your communication cadence is probably the number one thing that you can do.

MATT: What does the cadence mean there?

ZOE: So to me that means saying, okay, our entire organization will connect this many times a year in this many ways. And so there will be an all-department meeting once a month, once a quarter, whatever is appropriate, and that we will cover these three priorities and in broad progress and how it’s impacting the business overall. And then the expectation would be that the smaller subsets of teams are meeting in this way. The leadership team is meeting in this way, and you as the overall leader are connecting with your direct reports on this regular basis, and then making sure that you connect with every single person in your organization at least once every *blank* months.

MATT: Are there some things you think are unique to how Upwork is structured or some processes you have like that, cadences that you have, that you’d want to share, like best practices? 

ZOE: One of the things that is actually one of our greatest tools, which is a tool that I — everybody has got their own variation of it. Internally we use Upwork Messenger, the Dash Team. And there is just constantly the ongoing conversation that people have. So there is obviously a lot of work that gets done in that way. But there is also the check-in about like, “Hey I know your daughter should be hearing back from colleges she applied to, is everything going okay? Did she get into the one she wanted to get into?” And just building that camaraderie and that understanding. That’s not something that’s unique to us, it’s something that is drilled into us that we will continually make sure that we are connecting on a personal level as well as a professional level with individuals.

MATT: Just from the culture? Or the tool does that?

ZOE: From the culture as much as anything, and the tool really facilitates that for us. So for most of us that’s the first thing we do that’s work-related every day. So for my organization, we have a room for the leadership team and the first thing we do every morning is check in, say good morning — any personal updates, anything like “The kids are fighting so I’m going to be late to school and then late to work,” or whatever it is, right? 

And then it’s, “Here are the three things I’m going to do this day, and I need your help in this thing. And, oh my gosh, the meeting we thought was a fortnight away is now next week! Can you help me get those metrics that I need earlier?” And it just allows us to constantly be recalibrating the work that our teams are doing and connecting them back to the bigger, broader picture of what we’re doing.

It’s really simple. I feel like I should have [these] massive words of wisdom for you and I don’t. I think it’s just, talk more, communicate more, be clear about what you’re asking and clear about when you need help.

MATT: Just because it’s simple doesn’t mean it’s easy though.

ZOE: No, that’s true. I mean it’s really hard, right? And if everybody could communicate well I think a lot of things could be different.

MATT: Is there something different you would look for when hiring someone to work in this kind of environment than you would if they were going to come into an office everyday?

ZOE: Obviously it won’t surprise you: Are they a good communicator, do they ask quickly for help and self-identify and see that as a strength that they’re asking for help versus a threat or a weakness. 

MATT: But how do you screen for that? 

ZOE: I’m a big believer in behavioral interviewing and asking for really specific examples and then walking people through scenarios and saying, “Hey, this happens” — and often it’s something that’s literally happened the day before — “What do you do in this situation?”

MATT: I know that one thing that Upwork does is these meetups.

ZOE: Yes.

MATT: From an HR point of view, what are the pluses and minuses of these meetups?

ZOE: [laughs] That is a great question. The pluses are getting together. Nine out of ten times that is really fantastic. It’s an opportunity to put a face to a name, it’s an opportunity to share more personal stories, connect, to see how the work that you’ve done has made life easier for me and vice versa and all those things. And to brainstorm and just have more synergy. Sitting around, talking over a cup of coffee, you do tend to come up with different ideas than if you’re in an official meeting. 

Challenges can — it can sometimes be easier to relate to somebody via a screen. When you’re in person maybe there is just something you guys don’t like about each other, right? That can be hard. It also sometimes can feel forced, or like it has to be absolutely brilliant or it’s been a failure because they happen infrequently. They cost a lot of money, there is a big opportunity cost.

MATT: And yours are longer, right?

ZOE: Yes, right.

MATT: I’ve heard 10 to 14 days?

ZOE: They do tend to be long. So you’re also going deep for a long time with a group of people that you’re used to one very specific type of interaction with. And as much as we have hangouts that celebrate people’s birthdays, or whatever it is — 

MATT: Wait, say that again. You’ll have a virtual hangout on someone’s birthday?

ZOE: Yes, absolutely. We love a virtual hang out. Probably not the greatest HR example but there are definitely virtual happy hours that happen with distributed teams around here.

MATT: Sure. [Being] in the same time zone helps that.

ZOE: Yes it really does. That’s when you’re like, “Ugh it’s 6:00 in the morning, no can do.” The challenge is that it’s a group of people. And you get any group of people together for X period of time — think about Thanksgiving. Lots of pros for Thanksgiving, also some cons when a family that’s not always together is together for an extended period of time.

MATT: I think much like Automattic, some Upwork meetups often happen and people stay at Airbnbs and stuff.

ZOE: Yes.

MATT: So that co-living is an additional variable. And by the way, you have to check the Airbnbs sometimes. We’ve definitely had it where something they listed as a bedroom was actually — you had to walk through another bedroom to get through and things like that.

ZOE: Oh yeah, no, no one wants that. One of the big things that I personally advocate for a lot is making sure that all employees, but in particular women, when they’re traveling, never have to be at a place that has — their bedroom door is a door to the outside. Just from a safety perspective, like an emotional safety perspective. I want you to have a hallway, I want you to have somewhere that feels safer than that. 

And just making sure that physical safety is something that you’ve been really clear about with everybody, like here are the expectations around that. And being flexible. If somebody gets somewhere and is like, “I just can’t,” then you’ve gotta have some wiggle room around that. And so that may mean a buffer in your budget, which hopefully you don’t need it.

MATT: To get a hotel room or something.

ZOE: Yeah, like you need a separate hotel room? Totally fine, I get it.

MATT: You probably want to avoid cross-gender sharing of those…?

ZOE:  Yes, yes.

MATT: Dishes and clean up.

ZOE: Ohhh dishes, yes. 

MATT: I feel like you have something to say there.

ZOE: Sorry, I can — apparently that just hits a sore spot personally. It brings back bad roommate situations.

MATT: Tell me about dishes.

ZOE: Yeah, right? Who’s going to clean up the mess? Is there a rotation, is that clear, is that part of it? And this certainly, I heard a story about this, like an expectation about who was doing the keynote was based on gender, or there were two people with the same name, one was a woman who was a very senior leader, one was a relatively junior team man, who was a man. And it was first name only on the thing, and one of them was doing the keynote. And one of the remote attendees was like, “Oh I just assumed it was him.” 

MATT: Hmm.

ZOE: Okay. Well A, whoops, you should know more about the organization to understand who is the leader in this situation. So I just think understanding that but also understanding specific — especially gender roles in different cultures. You don’t want to get into a situation where the expectation is that the woman is doing the dishes or whatever it is, or the men are taking out the rubbish all the time. You’ve got to just be intentional.

MATT: You just said something really key as well, which is “across different cultures.”

ZOE: Yeah.

MATT: If you’re distributed and coming together, there might be people from — ten people from ten different countries — 

ZOE: Absolutely, right.

MATT: — and it’s easy to forget that. People live different in different countries. So you almost need that defined for your company. What are those expectations and the habits and culture of how you want to operate?

ZOE: Yes. Again the more proactive communication you have about this, the better off you are. Because it’s not just things about gender. Does everybody eat meat? Are there religious ramifications for how meat is prepared? All of those different things. Are there people who pray before dinner? What are the expectations of this? Do you have somebody who is a nursing mother who is going to need time to pump in between the schedules?

MATT: How about mentorship and learning and training? How do you do that particularly across your full-time versus freelancers? 

ZOE: We have tended to focus on our full-time employees in terms of learning and development initiatives. One of the things about freelancers is, by the nature of their work they are re-skilling at a higher level than the rest of us who are in these corporate jobs. 

MATT: It’s almost more Darwinian, being in the open market.

ZOE: Yes, they’re doing it constantly. They are much more aware of what is going on in terms of the influx of need for skills and things such as that. The research that we have done shows that the half life of a skill is about five years right now. So if you are an independent business who is working to garner your next project and the next client, you are much more mindful, and as such I should learn X new thing. So often we learn from that part of our community, “Oh goodness, we should be training on blank.”

MATT: Diversity and inclusion is something that usually is covered by HR. How do you think about that in a distributed organization and a global organization like you all?

ZOE: We’ve done frankly a lot of self-reflection. We worked with Paradigm, who is a consultancy who have a lot of attention right now, to re-evaluate every single full-time-people process in the company last year, which is not a small thing in terms of scope but also not a small thing when you really think you’re doing very well, and you care a lot, and you’re trying your best to realize all the places you’re flawed and can do better. By the nature of how our organization is structured, and the fact that it is a small portion of the people who are working to make Upwork “Upwork” that are full-time, we have a huge amount of diversity already due to the nature of the freelancers who are working with us at any given time. 

MATT: As we close out, your biggest tips. Let’s say someone new is joining and they haven’t worked in a distributed manner before. What do you point them to?

ZOE: I point them to learning as much as they can about how our business works and the different roles that people have organizationally. I point them to not being shy and just proactively communicating. Like, “These are the four things I’ve been asked to work on, I understand these two really well, this one I think is like this — can you help me figure that out? And this fourth one, I’ve got no idea, I’ve never even heard of this before, who can help me?” 

And then really making sure that they understand how their piece of the puzzle is impacting this incredible mission. I think every person who is associated with Upwork believes in our mission and our vision. And you feel it when you work here. And hopefully you feel it coming in and visiting us. 

MATT: What is that mission?

ZOE: Our mission is to create economic opportunity so people have better lives. I’ve worked at many different places and you see values on the walls and you see a mission, and people talk about it. But I’ve never been in a place where the values are used to make business decisions at the executive staff level. It’s really inspiring and I think that makes everybody eager to do the very best that they can do while they’re here, because it’s not just for us.

MATT: As we look forward, from your HR point of view you’ve seen how work has changed. Twenty years from now, what percentage of jobs do you think are distributed?

ZOE: Gosh.. 70? I think a vast majority are going to be.

MATT: Wow.

ZOE: Because real estate is so phenomenally expensive, the things that are just happening to make it easier even than it is already, and I would say it’s really easy right now to do it. It’s going to be a non-issue. It’s going to feel like I’m here with you if you’re in Singapore and I’m in Sydney. It’s not going to matter.

I think the beauty of that is the world gets smaller and we learn more and we understand more, we have more diversity of experience in our day-to-day lives. I look at my grandparents who traveled a fair amount, but the people that my children know versus the people that they know — their circle will be so much broader and they will have so many more inputs. So that can only be positive for business, right?

MATT: That sounds like an amazing world for our current or future children to grow up in.

ZOE: It does. I hope so.

MATT: Thank you for [being] part of helping to create that at Upwork and also with sharing your stories for the listeners here. 

ZOE: Thank you very much for having me, I appreciate it.


HAN YUAN: My name is Han Yuan. I’m the head of engineering for Upwork. I have been at the company for three-and-a-half years.

MATT: Had you worked distributed before joining Upwork? And how is engineering from a distributed or non-distributed view?

HAN: I have under multiple contexts. I think both from a, “I’m at a company and we have multiple offices around the world,” and also in situations where we had one or more agencies that we worked with directly and we collaborated in more of a — I would not say black box but more like a white box way. So really engaging with agencies in a staff augmentation way.

What’s fascinating about Upwork is that we’re pretty distributed. When we look at the engineering team they hail from over 40 countries around the world.

MATT: Wow, like currently living in 40 countries?

HAN: Right.

MATT: And that’s of the 350.

HAN: Right.

MATT: But we’re in an office right now in Mountain View. 

HAN: Mhm.

MATT: Tell me about that.

HAN: Typically we try to make sure that all of the key meetings happen between nine to five West Coast time. 

MATT: Do you have many people in the Asia Pacific time zones?

HAN: We do not.

MATT: That makes sense because those core hours would be tough to keep there.

HAN: Most of our personnel is somewhere between South America, Europe and Eastern Europe. We also find that because we have an agile organization, the leads of those agile teams are oftentimes not here in Mountain View. And in a sense they do have the authority or they’re expected to recruit and hire for their own teams. There is a tendency to hire within one or two time zones of wherever they happen to be. Geographic dispersion of our team is probably partially organic in that sense.

MATT: You come into this Mountain View office about how often?

HAN: I come in about four to five days a week.

MATT: Oh yeah, that’s pretty good.

HAN: I still come in pretty regularly.

MATT: What do you like about it?

HAN: I think I like the routine a little bit. And some of it is just my own personal situation where it’s harder for me to work at home. We also happen to have most of our product managers on premise. And so collaborating face-to-face with the product managers [and] designers is a key part of my job, and so I do tend to come to the office pretty regularly.

MATT: How do you keep the folks who aren’t here as in sync?

HAN: I think that’s a really good question and that’s probably one of the greatest challenges of leading a distributed team. And it breaks down to a couple of things. One is, “How do you maintain a consistent culture?” That’s a very difficult problem. 

MATT: What does culture mean to you right then?

HAN: In a lot of cases it has a lot to do with how both the big and small things regarding how people interact and communicate with each other on a day-to-day basis and what their expectations are. So for me, it’s being very, very explicit in certain cases what people expect from each other. 

So for example, how long can you sit on a pull request? Can you sit on it forever, can you sit on it for one day, three days? Without that code in place, different engineers from different parts of the world have potentially different points of view on what is being responsive to a colleague.

And so we spend quite a bit of time documenting and being very explicit about what we expect in terms of behavior from our engineers. And hopefully to the extent that we’re consistent, we reward and we also give feedback for behavior when it’s inconsistent. But I think that’s a key part of it.

MATT: Yeah.

HAN: The second thing I think is more of a practical thing, which is we generally bias towards hiring people who have strong written communication because we want to do things as asynchronously as possible. In order to do that, being able to write well is very important. I think chat is less interesting to us in general because it’s a little bit synchronous in nature. And so we want to encourage our engineers and our team to really put things down thoughtfully and clearly.

And then along those lines, as an organization, we spend a lot of time trying to create transparency within this working operating system of how we build the site. And so a big part of that is making sure that when there are issues everybody understands it, even from the executive standpoint — the engineering executives — and then also having the ability for teams to propose and communicate innovation at all levels of the organization or recognize people at all levels of the organization. And so we have various mechanisms to achieve that. 

MATT: You mentioned if I were going to make a proposal you’d want me to write it out and really present it. How about when there are those technical agreements? Two great engineers, maybe on different teams, or maybe the same team, have a difference of opinion for which way they should go. How do you work that out, especially when you can’t get people around the white board or in the same room? 

HAN: In a distributed organization there is a tendency, and rightfully so — you have to have some structure where you say, “Hey you are the CEO of this problem.” And so there are times when I may come to an engineer or engineers come to each other and say, “Hey can you make this change” or “I’m really worried about this thing that you built, you should make this change,” and as the owner, of course, you could say no. But in that sense the decision making is very clear and absolute. But we have seen situations where the decision was the wrong decision or multiple people came to that decision maker and said, “I really think you guys are doing a bad idea,” and they said no multiple times. 

And so over time, in order to flag these issues, what we encourage teams to do is, as soon as you have come to a place where you disagree, you follow our proposal process, which is the same format: State your problem, state each other’s point of view, and then bring it to the adjudicating body, which in this case would either be an architecture review, or we have a different body called eng staff, which is the top 30 senior people in the engineering organization, to adjudicate over this.

MATT: You had something really key in there I wanted to ask about. You said “make the other side’s arguments.” Tell me about that. Because that’s not a normal thing to do. Normally if I’m proposing something I would just make my argument.

HAN: We really want to encourage empathy in general. And so a key part of empathy is being able to try to see the other person’s point of view. And in an organization as distributed as ours where people come from all around the world, we view it as an essential ingredient to developing deep and meaningful collaboration.

MATT: What do you think is the main benefit of what you do that couldn’t be accomplished if you had a traditional office approach like you did in prior jobs?

HAN: I think there’s a bunch of practical things that people would often say, like, “Oh, we can do 24-7 development” or “you can have access to talent.” And I think those are valid. But if you were to ask me, the most important thing is diversity of thought. And I think that has a lot to do with different people from different backgrounds and different parts of the world who have experienced different things and have worked on different things, and that is quite powerful. I think when nurtured well it creates the conditions for things like creativity, empathy, collaboration, and things like that, and I think that’s very valuable.

MATT: Can you share an example where that came into play or you felt like that improved the outcome?

HAN: It happens oftentimes in big and small ways. For example, because people are very aware that they come from different places, they tend to ask more questions, which I think does elicit a little bit more thought from other people and it also forces people to normalize their communication, their language, and their reaction to things, that’s a little bit more neutral. But these are very subtle things. Diversity of thought comes from the place of actually interacting with somebody who isn’t very familiar with how you do things.

MATT: Are there any commonalities or practices of the highest performing engineering teams? Do they do daily stand ups? What sort of things do they adopt?

HAN: The highest performing teams actually have much smoother communication between the product team and them. There is context setting that — the transmission of context is just cleaner because when that happens, the engineers are brought into the solution space, not just in the implementation space.

MATT: Yeah. So let’s say I was leading an engineering team that you perceived [to be] bottom quartile at the company, wasn’t doing as well. How would you coach me to have a better context setting or connect better with my colleagues to be more effective?

HAN: For all of our groups we have them document what their vision and values are for that team and align around what’s important to them. So for some organizations, for example, if you’re on a platform team, you may value very, very clean code, maintainable code, and you may value doing things very well over speed. For teams that are working on things that don’t have product-market fit yet, we encourage them to break things, write things a little bit on the side, and that’s fine. And they can go ahead and say, “Hey this is what we’re going to do,” and explain why we’re going to do it.

MATT: How about in-person versus remote? Let’s say I was this engineering manager in Houston and I was like, “Hey there’s this product person in Mountain View I’m just not connecting with.” Would you encourage us to get together physically or are there meetups? How does that work across the full-time and non-full-time people?

HAN: In almost every case team performance has improved after they’ve met face to face. Once. [laughter] Now the gains that you get from meeting up twice, three times, four times, a hundred times, tends to fall off quite a bit. 

MATT: Diminishing marginal utility.

HAN: Exactly. But the first time the gains are huge. So we typically fly groups of 30 or 40 folks on meetups. And since we’re so distributed it tends to be some kind of random city on the planet that is more or less geographically accessible to those teams.

MATT: Those would be freelancers and full-timers?

HAN: Yes. 

MATT: Cool.

HAN: And then these meetups can last for a week to two weeks. So that’s usually enough facetime for people to get a feel for how they work.

MATT: Yeah. You mentioned you find it hard to work from home when we started. Tell me a bit more about what you find challenging working from home or not?

HAN: I think this is a personal quirk apropos of nobody else. But I really like to partition when I’m working and when I’m not. And to your point about isolated time, even during the work day, I have not had this in six weeks but historically I try to block off at least three hours. When I write code, and I still do from time to time at home, not at work, I’ve done a bunch of performance studies on myself and I know that I can only generate about four and a half hours of solid code. I’m very —

MATT: I’m curious how you knew when it started to drop off.

HAN: So if you really want to know…

MATT: Yeah.

HAN: This is what I did to myself. I would measure blocks of time of 30 minutes and then set a timer and every 30 minutes I would tick on a scale of one to three whether or not I did what I thought I was going to do in those blocks. When I start the next block I tell myself what I want to accomplish and then — 

MATT: Very Pomodoro-like.

HAN: It’s very Pomodoro-like. This was back when I was, I would argue, gainfully unemployed, where I was working on my own thing. I ran this over ten hours a day, seven days a week for about 12 to 18 months. And so I had significant data on how I work and I found out that, generally speaking, my prime hours are somewhere between 11:00 and 3:00. And so once I figured that out I —  

MATT: Morning or night?

HAN: During the day. And once I figured that out I was like okay, in the afternoon I’m going to go hang out, work out, do other things. As a result I feel like, at least for myself, I have a few hours that are good and most of it’s not so great. 

MATT: That is utterly fascinating, first. What other variables did you find?

HAN: Sleep was really important too. So when I started to correlate the number of hours that I slept, that was really important.

MATT: How much do you need there?

HAN: I typically need six and a half to seven hours. 

MATT: I do want to talk about tools a little bit. What are the tools that you use when you share this writing or these proposals? What do you rely on there, particularly on the engineering?

HAN: Day-to-day collaboration — I would say our most important tool is actually the G Suite. Being able to co-author documents in real time, comment, assign action items, it is a game-changer for us, especially when it comes to assembling information very quickly. When we have site incidents, for example, we really need to make sure that a document is written quickly so that it’s fresh on the top of people’s minds, and then we run the post mortem. That level of tooling is critical.

We have a messaging client on our platform which we use for day-to-day business but the challenge is that when the site is down, oftentimes our messaging system is also down, because it’s part of the same platform.

MATT: Oh yeah. What’s your fallback?

HAN: Yeah, so our fallback is typically Slack. And so Slack is still very important. In order to reduce mean time to response our tech ops team and site reliability teams always collaborate on Slack, and so they’re basically online on Slack. We also use Hangouts quite extensively just for video collaboration. But also during site incidents, Hangouts are important because usually —  

MATT: You’ll spin one up?

HAN: We will spin them up just because we have found that chatting back and forth is usually not fast enough. Hangouts also give us the ability to see what’s on each other’s screens. And so during those kinds of events it’s actually more important to watch an engineer type instead of look at their face, their panicked face. [laughs] So I think that level of collaboration is very, very critical and that’s when we need to go full real-time but remain distributed. Everything else is probably standard tech text stuff, like Git’s important, things like that.

MATT: Jira, Github, what’s the — 

HAN: We use Jira, and then, essentially all the Atlassian stuff like Bitbucket and so on and so forth. We don’t dictate what the engineers do on their own machines. We have a “bring your own device” policy and so people use different kinds of tools.

MATT: Favorite thing about distributed work?

HAN: The people you meet.

MATT: Least favorite thing?

HAN: Miscommunication.

MATT: Especially across cultures and languages, right?

HAN: Yeah.

MATT: Final one. Twenty years from now what percentage of jobs do you think will be distributed? 

HAN: I think almost all cognitive labor can be distributed. I don’t know how many companies or what percentage of companies will be fully distributed and I think there will probably be a spectrum of fully distributed companies, like Automattic, and partially distributed companies. 

MATT: Pick a number over all and we can check it in 20 years.

HAN: I would say most companies will be partially distributed. And that maybe 20 percent of companies will be fully distributed.

MATT: So that would be 35% of jobs?

HAN: Yeah.

MATT: Cool. I really appreciate it.

MATT: That was Han Yuan from Upwork, and before that you heard Zoe Harte, also from Upwork. You can follow Zoe on Twitter at @ZoeSHarte, that’s Z-O-E-S-H-A-R-T-E. Han’s not on Twitter, but he’s pretty active on LinkedIn — just search for Han-Shen Yuan, that’s H-A-N-S-H-E-N-Y-U-A-N, and you’ll find him. 

As the world’s largest network of freelancers, Upwork has a big opportunity to define what distributed work looks like in a big, blended company. I’m glad that they have such thoughtful people throughout the organization who are thinking hard about how to create economic opportunity and great work experiences. 

Next time on the Distributed podcast, we’ll be speaking with someone I’ve been working with for a few years now. John Maeda is an author and a certified design guru, if there is such a thing. He also happens to be the Global Head of Computational Design and Inclusion at Automattic. We’re going to talk about how the distributed model impacts design teams, and about the tools and processes he’s using to foster creativity among them. 

Thanks for joining us. 

Automattic CEO Matt Mullenweg on building a fully distributed company

Read Matt’s history of Automattic: “On Building Automattic.”

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

On today’s episode, Automattic editor Mark Armstrong interviews our usual host Matt Mullenweg to discuss the history of the company and how its distributed culture emerged from conditions that many startups face. They go deep on the tools and processes Automattic has developed to keep everyone connected, even if they’re scattered across the globe.

The full episode transcript is below.


Mark Armstrong: Hi everybody. Thanks for joining the Distributed podcast. I’m not Matt Mullenweg, I’m Mark Armstrong. I’m the founder of Longreads, which is part of Automattic, and I’m on the editorial team working with Matt on the Distributed Podcast.

So today I wanted to take a step back from the interviews Matt’s been doing and find some context for how Matt got here in the first place, how he became interested in distributed work, and it all starts with the history of Automattic. So that’s what we’re going to talk about today. We’re going to talk to Matt about how he got here, how he actually decided to build a company that had no offices, and what worked and what didn’t. Thanks for listening.

Now where are you right now?

Matt Mullenweg: I’m actually in San Francisco, California.

Mark: And I am in Seattle. This is basically how we record this podcast for people who are remote. We have a Zoom connection, we use GarageBand, a tool called Zencastr, and we put it all together and it sounds like we are having this intimate conversation right next to each other. But this is a very good symbol of how distributed work has changed and the technology has changed.

Matt: Yes. 

Mark: So take me through the very beginnings of Automattic and how you ended up with a distributed work model in the first place.

Matt: Well at the very beginning I had moved from Houston to San Francisco, actually, to take a job with CNET Networks. And they were actually an early adopter of WordPress. So they offered me a job as a product manager to drop out of college in Houston. I drove across the country with my mom and got a little apartment in San Francisco.

Mark:  Did you apply for the job?

Matt: So what had happened was, I had said if I hit number one on Google for the search term “Matt” I would shut down my site and go out on top, like MJ. So that happened. Partially because most WordPresses included a link to the main developers, of which I was one. And they all said “Matt” and so those links started helping me rank first for Matt. So I just replaced my site with a little black screen that said this happened and I came out to San Francisco. Because this got some news when this happened. A bunch of people reached out.

Mark:  So at this point, you had already started WordPress. Did you already have in the back of your head the idea of building a company around WordPress or were you thinking, well this CNET thing will work out for a couple of years and see how it goes?

Matt: I’m guessing this was probably 2004. At the time, there was no indication that anything related to WordPress could ever make money. [laughs] It was very much a voluntary project. And there weren’t really examples, certainly not as there are now, of consumer open source becoming a commercial thing. But what I did know was I was already collaborating with folks all around the world having a blast and using basically all my free time to get online, hang out in IRC, which was kind of like an early pre-Slack chat system, and basically code with these people who were also passionate about making publishing easier.

Mark: So you’re doing all this work on something that you love and then you’re commuting into an office in San Francisco. What was the office experience like? Was this the moment where you were like, “I never want to work in an office again so I will never do that?”

Matt: No, the opposite. It was amazing. [laughs] CNET was one of the first companies to actually set up a headquarters in San Francisco. Most of the major companies were and are down in Mountain View or Cupertino or some place else in the Bay Area… San Jose… But I looked very, very close to the CNET office and then when I moved in, my patron there, a guy named Mike Tatum, got me this really cool office right above the door, like a corner office. 

And I remember this VP came by and in the course of the conversation, “Hey, where are you from, how are you doing, what you going to do here,” etcetera, he started to look around and be like, “Man, this is a nice office.” You can guess what happened next. Two weeks later I come to the office and there’s a note on my door. “Oh we’re doing an office move.” And I got moved to an interior office in the same section, still on the third floor, but more of an interior, non-window office. 

But then there was a general re-org in the group I was in, and that whole floor got taken over by GameSpot. That was doing really well. And they literally moved my group into the basement, [laughter] the very, very first area. So now I was not just no-window, I was in this very small area and that was around the time I think I started to think this might not be for me.

Mark: So you’re putting together the idea for Automattic as a for-profit company that then would contribute to the WordPress open source project. So you’re viewing this as an opportunity to merge the two ideas of the non-profit, open-source side and a for-profit company that feeds into it. Is that the original idea?

Matt: So the original idea I actually pitched at CNET. They had a lot of cool domains, famously com.com, download.com. And one day I got a list of all their domains. They had probably a thousand from different acquisitions and stuff. And I went through them and I was like “All right, well, could be cool.” And I came across one called Online.com. 

So the idea in the pitch I made to them was let’s make a version of WordPress that anyone can start with. So instead of having to know PHP and configure a database in FTP and all these things, let’s make it self-serve, where you can just click a few buttons and get one. That could be Mark.online.com. It could be your online home and you could have a blog and a profile and all this cool stuff. So I really pitched that quite vigorously.

But at the time what was going on was this colossal battle between blogs and traditional publications and two, every single internet giant had a blogging system but they were scared to call it blogging. So Yahoo had one called 360, AOL had Journals, Microsoft had something called Live Spaces, and then of course Google had Blogger. And so it appeared that all the internet giants — and those were the internet giants at the time — all had something in this space and CNET, one, thought they couldn’t compete, and two, thought that blogs were just gonna be like noise and politics and mess and junk and they were really going to bet on professional publications. 

They were at the time locked in — News.com, which was a tech publication, was battling — or ZDnet was battling with Gizmodo, which was one of the early blogs started by Nick Denton and the Gawker Network, and Engadget from Jason Calcanis and Pete Rojas and those folks were also just getting started. So they saw themselves locked in this epic battle of professional versus amateur and didn’t want to do with anything related to blogging. 

So I said “Well, I have to do this. I’m going to leave and start this.” And CNET very graciously invested in what became Automattic but asked if I could stay a few months to finish up some of the projects I was working on. So I did. But in those few months, I went ahead and started Automattic. I already knew the people I was working with as the other lead developers of WordPress and started trying to convince them to leave their jobs. [laughs] 

And the first one actually was a fellow named Donncha Ó Caoimh, who was over in Blarney, Ireland. And he had started a different fork of the software that became WordPress. His was called B2++, I believe. And we decided to merge that with WordPress and make that WordPress Multiuser, which later became WordPress Multisite — basically a version of WordPress that was multitenant, that could have lots of people clicking a few buttons and starting a blog. And I want to say the second was either Ryan Boren or Andy Skelton. And I was technically the third because I stayed a few extra months to finish up things at CNET, and then we started Automattic.

Mark: Already you’ve built the beginnings of this company and you’ve already got employees that are spread out all over the world. So was that simply, “Okay well, these are the people I trust and want to work with and so we’re going to build a company that way,” or was there more deliberation around that?

Matt: One aspect was definitely having no money. [laughs] I was just paying Donncha and these other folks out of my CNET salary basically, and for servers and things, starting to rack up some credit card bills. So it was very much like — well, moving is really expensive [laughs] and we’re already working together, and, in fact, those were the days when we’d all work very, very long hours. So if you’re working 10 to 16 hours a day, you’re overlapping quite a bit with someone who is, say, in Ireland. And we had this awesome, almost relay thing where I’d work until night and then he would wake up and start working. And then I’d sleep, wake up, and there’d have been a whole cycle of things done to the software. It actually allowed us to iterate very quickly and brought in some asynchronicity very early on to our interactions.

Mark: At this point, how are you communicating with each other?

Matt: Probably we used AIM. AOL Instant Messenger, which is now shut down, IRC, and we were either still on SourceForge, which was kind of like an early GitLab or maybe at this point had switched to hosting the code on WordPress.org.

Mark: So this is a lot of baseline foundational communication that sounds very familiar to me even in current day Automattic.

Matt: We actually still run IRC servers to this very day. [laughs] And some people like to use them.

Mark: Yes.

Matt: But the evolution at the time, AIM was definitely the most popular chatting platform. At some point we switched to Skype again for chat, not really for voice. But I do remember some of those early voice calls where we, for the first time, would talk to each other and have what maybe [were] our first meetings. And the average meeting cadence at that time was probably three per year. We didn’t do a lot of them. It was really very much a written communication style.

Mark: And you hadn’t met in person yet.

Matt: None of us had met in person. Around that time was when I hosted the very first WordPress meetup in the world, which ended up being eight people at an Indian place, which is still there on Third Street, called Chaat Cafe. Those eight people ended up being pretty interesting. There was Chris Messina, who at the time was involved with Drupal Project, and would later go on to invent the hashtag. Scott Beale of Laughing Squid, which is now a large WordPress webhost. Om Malik, who was a journalist at Business 2.0 and later started GigaOm, became one of the earliest WordPress users. And someone who I met for the first time, which was Ryan Boren, who was one of the first major contributors to the core of WordPress. And he was, I want to say, an embedded systems engineer at Cisco. 

Mark: There is a point though where you are going to then bring Automattic to investors and raise some money. How did they react to this idea that you didn’t have an office, [where] everyone was all over the place?

Matt: We didn’t really plan to raise investment in the beginning, we were just focused on making money to be honest. So we thought that we could have add-ons for WordPress.com. I think some of our early ones were custom CSS for customization and domain names, so this would allow people to be a business model. This idea of ringtones for blogs so you could buy customizations or add ons, actually not dissimilar to what we do today. And then we started to also do partnerships with different hosting companies who provided hosting and then could pay us for essentially new customers.

So that was the early business model and that started to make a bit of money, enough where we could each take a modest salary of a few thousand a month. And that was the plan. We didn’t have a ton in the bank, there was enough for a few of us to work on WordPress full time. And that was really just a dream. I mean, the company was created to have a place where we could be paid to contribute to open source and so we were all happy as clams.

Mark: It seems like you had gotten far enough along with the growing group of contributors and employees that you were already proving that distributed work was working. So by the time you ended up bringing in outside investors or other partners, that wasn’t really a question anymore. Is that right?

Matt: I met some different investors, folks like Tony Conrad and others, but I was at this point 21, [laughs] so, pretty young. And that was the era, pre-Zuckerberg, pre-all these other things, where you brought in adult supervision. So the model was really Eric Schmidt. Adult comes in and professionalizes the business. 

And I didn’t really want that until Om Malik introduced me to a fellow named Tony Schneider, who had sold a company called Oddpost to Yahoo It was the original Ajax Gmail predecessor that allowed you to have a very web-application feel in the browser. They were the first to do that, that I had seen. But he wasn’t going to stay at Yahoo. So Om had done a cover story on the company for Business 2.0, and he said, “Hey you’ve got to meet this kid from Texas.” And he told me, “Hey you’ve got to meet this guy Tony, he’s not going to stay at Yahoo too long.” 

So we met and really, really hit it off. Tony is an amazing individual. He came from Switzerland, moved to California, ended up going to Stanford, had a few start ups under his belt, including this very successful exit at the time to Yahoo, and was a CEO. And I was like, “Ah, this guy is my business soulmate.” If this is the adult, [laughs] I can totally bring in an adult — this guy is amazing. And I learned so much from him.

That was with the expectation, that Tony would join the following year when he was able to leave Yahoo. [He] ended up raising the first round for Automattic, which was about $1.1 million from folks who we actually still work with today, like Phil Black at True Ventures, Doug Mackenzie, Kevin Compton at Radar — so that first early round. And I was the CEO for I forget how long, the first however many months before Tony joined, and then we started working together.

Mark: Was there ever any pressure to eventually — “Okay, this is great, I love distributed work but we also need some physical offices?” How much pressure had come in, in those early days?

Matt: Well first we’d just use our investor’s offices. So at the time Blacksmith, which was the predecessor to True Ventures, had a space in the Presidio. So Tony and I would just get together at restaurants and coffee shops and then, if we ever needed to have a meeting or something like that, we’d go to this awesome office in the Presidio. 

Later True, when they formed, moved to this awesome pier called Pier 38. They very presciently were like, “Okay, we’re a VC, we’re only this many people, but we can get this office space that’s a few thousand square feet. Let’s just put a few tables at it.” So one table was GigaOm, one table was Automattic. Upstairs was Bourbon, which later became Instagram. So there was a cool center of early startups that would have a little desk here.

Tony and I would go in there and meet or work from there but there was no reason to try to move the rest of the company there, because they were perfectly happy being where they were. I think Donncha was just about or had just gotten married. Immigration seemed really tough; there were a lot of barriers. So I was like, “Well, this is working, so let’s just continue to hire people wherever they are.”

However at the time it wasn’t clear that that was the thing we were always going to do. A lot of investors said, “This will work when you’re 10 people or 15 people, but at some point you need to get an office or you need to bring everyone to one place.” So we always kept that in the back of our mind as something that we might need to do. And [we] always had this small headquarters, first a desk, in the True Ventures space. And then we moved across the hall to a bigger space where we hosted lots of events and meetups. 

This idea that we needed something to be the official address of the company persisted really until… gosh, when did we shut down our office? Was that 2016?

Mark: It was a couple years ago, mhm.

Matt: We actually continued having a headquarters really until then. Partly this idea that on average, as we started to scale, about ten percent of the people we hired were in the Bay Area, and the ones who did like to go into the office in San Francisco. We assumed as we got bigger and bigger that the ratio would continue at 10 to 15 percent. And it turns out it mostly did. 

But what changed was that traffic and everything got so bad, parking got so bad in San Francisco, that even the people we’d hire in the Bay Area didn’t really want to commute. And then the tools for collaboration got better and better and so they didn’t really need to.

Mark: It’s interesting because there is a lot of this early Automattic history that you’re in San Francisco and you need to be in San Francisco physically in terms of the existing power and money, I guess, to be able to get a foothold for the company.

Matt: I think I felt like that as the leaders of the company we needed to be in San Francisco but the rest of the company didn’t. So it was great for Tony and I. We actually didn’t really have any new funders until 2013, 2014. And we were relatively unique at the time in that we had one West Coast VC, Blacksmith, later True, but our other investor was on the East Coast, called Polaris. So we were already distributed from our initial funding and that was unusual for an East Coast VC at the time, to invest outside of their geography.

Mark: Will we ever get an office back in San Francisco?

Matt: Yes, we probably will. [laughs] If something really interesting comes back up we’ll get a small space but it will probably be a secret. It will probably be just for board meetings and investor stuff, not something that is really an office like we have had in the past.

Mark: I want to switch over to some of the culture inside of Automattic since the early days. Automattic has its own creed. For those of you who have not read it before, you can go to Automattic.com/creed. But one key line from that is “I will communicate as much as possible because it’s the oxygen of a distributed company.” 

I know how it is today, and we can talk about that in a second, but in the early days did that mean that every single conversation was public, and there were no private conversations? What was transparency and communication like in those early days?

Matt: Yeah it really was, because there wasn’t really any reason to not have everything be open. The whole company was in one chat room. We had no teams, we had no managers, it was totally flat. We just organized around projects and code really. And there was such an advantage to knowing everything else that was going on. And we were doing enough things that you could know everything else that was going on and there was a lot of information sharing, or seeing the flow of code commits and code changes and conversations.

You got a shared collective intelligence of everyone at the company pitching in on every idea. So although we didn’t have formal product managers or a ton of designers or things like that, because everyone was using everything. We use WordPress ourselves, and seeing things that went through, you got a lot of real time feedback, almost like real time user testing with your colleagues, that ended up speeding up the iteration cycle and leading to some very usable products, even in the early iterations. 

Mark: That probably brings us to P2, [which] I believe was introduced in 2008. So for those who don’t know, P2 is essentially a WordPress theme for groups to share status updates with each other. I personally still see it as the foundational tool of all communication inside of Automattic to this day. But I went back and looked up your first post on Update-A-Matic, which is the all-company blog inside of Automattic, and I can see that you wrote the quote “Finishing up meetings.” That was the entirety of your P2 post.

Matt: [laughs] Well it was pre-P2. We just had an internal blog and we used it much like Twitter, which at the time was called TWTTR. The idea was just that — originally the prompt on Twitter, which is “What are you doing?” or “What’s going on?” or something like that. And so you would post literally whatever you were doing at that second. [laughs] So, finishing up meetings… 

Mark: This is like people tweeting what they had for breakfast or whatever?

Matt: That was the goal, actually. So a way for us to put things on there. And then we started to see that it was useful to have a place that you could have comments on or could do threads. We used it for keeping data. 

Mark: So P2 was not introduced yet as an actual thing, this was still just the internal blog?

Matt: It didn’t come until many years later. So it was really just this internal blog in IRC. What was, from the very beginning of Automattic, was this concept of meetups. Actually early on we did two ,I think, in one of those early years with five to 15 people. 

One that stands out in my memory, because it was an utter disaster, [laughs] was Stinson Beach, which is a place where I think we all fit in one, maybe two homes. We went on Stinson Beach, which is north of San Francisco, and we didn’t really know what to do at a meetup. So I think we assumed that we should just have all day long meetings and debates. [laughs] This drove, I won’t name who, but it drove someone crazy and it ended up being — I think there was a walk out of one or two people. [laughs] Voices may have been raised. It did not go well. 

At the time the valid feedback was, “Why are we sitting around, just arguing about things for hours and hours, not getting anywhere, not driving to decisions? And, by the way, we could do some of this written. Why does it need to be in real time, people reacting to information versus considering it, thinking about it and writing a response in a deliberate way?” Which — if you think about it — is a much, much better way to have a debate or an exchange of ideas than people just reacting in real time to whatever information is popping up in their head.

So that first meetup was a little bit of a disaster [laughs] and we decided to move them to once a year [laughs] and make them more organized. So we introduced the concept of meetup projects, or hack weeks. So the idea is we would get together and start and launch a number of things during that week as a way to do things we wouldn’t normally do, and just have fun. It was very much getting together and just working intensely alongside someone. [Which] was, and honestly still is really fun, [but] was hard to replicate with the tools at the time.

Mark: I think that holds to this day, this idea that the meetup should be a social event as well because you’ve got the entire rest of the year, and you have all of these tools in which you can organize and communicate and brainstorm. And so really pinpointing the specific things that you can only do in person together — and that’s also building relationships and building trust with each other — that you can then go back and be honest on Slack and P2. 

Matt: Exactly. Those meetup projects ended up creating a lot of things that became very crucial to Automattic today. So it evolved what first was called Prologue, which was the early version of a theme for WordPress, which put the posting on the home screen, so again, very much like a Twitter built on WordPress that looked a lot like what early Twitter looked like at the time, which was just a box and a list of posts.

And then that evolved at a later meetup into what we call P2, which basically took Prologue and made it real-time, so that as things were posted they would show up without you having to reload the page to get new comments or anything. So that was the evolution of what became what was and still is to this day the most important communication tool inside Automattic.

Mark: It’s an interesting segue to today because you’ve got P2 that are now hundreds of P2s, team and project P2 websites across the entire company. And then we have this global search tool in which people can search across every one of these websites. We also have a field guide which is more evergreen pages of documentation. 

But the P2 is where most of the deep communication is. And I’m raising this as a segue to today because seeing your original “Finishing up meetings” post and then seeing a post just the other day from Nick Momrik on our HR team, about the growing word counts of our P2 posts [laughter] as a trend, I think we can see that P2 has not fundamentally changed but how we use it has changed, especially once we started to embrace something like Slack.

Matt: Let me paint a picture of P2 so people listening can know what it’s like. So imagine on, kind of like a website, with a main area and a sidebar, and in the main area there is a post box at the top so you can type in there and click “post” and it shows up immediately, much like a Twitter or a Facebook. Below that is something that can be a post of any length but all the comments are in-line, so all the conversation happening next to a post, which again, doesn’t need a title, can be right there, and they pop up in real time. 

And on the right, on the sidebar, can be widgets that allow you to search, might have a list of people on the team, could have a schedule, could have notes, could have links to things, to resources, could have target launch dates or a countdown timer. And so the sidebar — it becomes kind of like your ultra-customizable home page for your team or project. 

The key for us was, as you mentioned — transparency was our default for most of our communication. The one thing that didn’t really work for that was email. So we’d email each other ideas and threads and brainstorms but then if someone new joined the team they had no way to catch up to those emails. And there was all this intelligence and data and wisdom being lost in people’s inboxes. 

Also, our email was busy at the time because support was all done through email and “support@” was just an alias for “everyone@.” So every support thread we got would go to everyone in the company and whoever replied first would claim that email or that ticket. 

So P2, Prologue, this internal blog, became a way for us to eliminate email. So anything that I would normally email, let’s say “Hey Mark, I’ve got this idea for a podcast, I think it should be X, Y, Z.” I would just post that as a blog post and you could see it whenever, and you still got that general intelligence that anyone else could see it and choose to interact with it or add their two cents to it, which is both a blessing and a curse. [laughs] It’s a blessing when you want the two cents and it’s a curse when you’re crushed under a sea of pennies. 

Mark: I want to go back to today. One could argue, at least from my experience — I joined, just for the record, in 2014 — but one could argue the past two years at Automattic have seen some of the most dramatic changes since you’ve started organizationally. We’ve grown very quickly. We’re now at 900 employees. And where we once were a strictly flat organization — we made up our own titles — we now have executive roles, product roles, and actual hierarchy. Can you talk about what’s changing and why at this stage and why it’s important?

Matt: Sure. A common misperception about Automattic was that we were non-traditional infrastructure. And that probably stems [from] — I avoided creating any hierarchy or really teams or normal company structure until we were maybe 50 or 60 people, and it became really, really necessary. So that’s where that comes from. But really since then, which is, by the way, the time chronicled in Scott Berkun’s book “A Year Without Pants,” which was — he was joining partially because I was like “Oh we need someone who’s done this before to help us create these teams,” but ever since then we’ve had a completely normal org chart, a completely normal hierarchy.

Although I’m a strong believer in how we work being non-traditional, distributed, it’s still really important for lines of accountability and for people to know where they fit and have one-on-ones and all those sorts of things. So that part of Automattic has always looked kind of normal. 

Mark: Essentially we’ve got team structures, which are — teams can be, what, eight to 10 people per team and they’ve got a specific focus? What is the ideal team size?

Matt: How we have approached Automattic is in a fractal way. So the idea is that if you zoom in or zoom out of Automattic it looks like the structure that is self-similar in many ways. So when Automattic was ten people, we had a designer, a businessperson, a bunch of engineers and we’d all work together to iterate on our area. 

So our team structure inside Automattic is very much modeled on that cross-functional idea where you get everyone together and you just — it’s that classic idea, a two-pizza team or whatever you want to call it. Get people working together with the autonomy and all the know-how that they need to ship and iterate with users, ideally as frequently as possible. Then when that gets too large, much like cell division, you split it into two identical teams and now you have two teams of, let’s say five doing cross functional work. 

As that grew, we eventually had divisions and now business units that are made up of divisions. Our largest business unit probably has two hundred and sixty people in both product and engineering and design. But still, if you zoomed in on one of those teams it would look very much like the teams that we had a decade ago.

Mark: And the tools too look very similar. So we still have the P2, as we’ve gone over, we use Zoom for video conferencing, as you and I are doing right here, then of course Slack came into the picture. That was shortly after I joined the company and that very much started with you, right? I feel like we were experimenting with it and then you decided let’s go all in.

Matt: I appreciate the credit. [laughter] With many things at Automattic, we give the teams a lot of autonomy. So we tried to adopt HipChat before other things that were a little better than IRC. It just didn’t take. I want to say probably the mobile team or there was some team inside Automattic that adopted Slack and then it was optional for people to get on it. Many, many did and we utilized their free version. 

I also knew Stewart from his Flickr days and so I knew a lot of the people involved with it. And in fact, a very early Automattician joined Slack pretty early on. I think she was one of the first 20 or 30 there. So we had that connection as well.

It just got so good. And my decree was more that we still had a chunk of the company that was really holding out on IRC and didn’t want to sign into Slack. And for communication tools it’s really, really important to have everyone on the same thing. And we were going through a lot of growing pains. Our non-IRC was mostly through Skype, or if IRC would go down we’d use Skype and that was just really awkward because then you would have to add everyone who joined the company manually. So it was just a very weird process. 

And so Slack, everyone being on there, the directory, all the things that everyone knows and loves about it, it was just so darn convenient. It really seemed like a better version of IRC. And, in fact, a lot of the conventions in Slack are directly modeled after IRC, like the reason why public channels have a hash in front of it. That is taken directly from how most IRC clients work. So it was pretty natural and, just for communication standardization, seemed important. So that was what I think eventually got our Systems team onto Slack.

Mark: I think it fundamentally changed how we even used our other tools, like P2. Whereas P2 maybe was more of a conversational tool in the past, now it’s a little more announcement-focused or this is our plan-focused [tool]. What would your take be on how P2 has evolved in the world of Slack?

Matt: It totally depends on the team. I would say this is one of the things that has changed most. I don’t know if it’s for the better but I’ll observe it in a neutral way. That as we hired more and more people that then come from the online collaboration or open source space — which, to be honest, there’s only so many people who have worked in an open source project or things like that. [laughs] They brought an approach to P2 that was a little bit more like announcements, like you said, and more meeting-centric, so needing more of that kind of synchronous real time communication and get everyone on the same page. 

And I think that coincided a bit with Zoom, which honestly makes meetings a lot easier than they’ve ever been and more pleasant than anything we’ve done in the past. So I think also people just wanted to connect better. We have a lot of psychological diversity in the company. I would say early on [we were] very much composed of introverts, including myself, for whom text was really our first choice of communication. And as the company grew, a lot more extroverts, or people who wanted to use voice or see each other as they converse. And so it was hugely controversial early on, even the idea that we’d have an audio-only meeting was widely debated for why that’s needed, if for nothing else than it’d be inconvenient for everyone not in a couple time zones. 

But teams can choose their own way. So as more and more teams had more and more people that were maybe composed of these or that wanted the real time synchronous communication and the tools got better, we started to use that more. And so on a team-to-team basis it varies a lot. 

I love, for example, our VIP team — that’s the enterprise part of Automattic — uses P2 I think the best of any team or division within the company. They put really everything through it. Their Slack is still busy but they really put a lot of thought and their P2 is great to read. It’s funny, it has GIFs, it’s fast, everyone has it pretty dialed in there.

Other teams have gone to where they might only make a few P2 posts a month, which if you’re doing that you’re not using it for daily communication, you’re not using it for real-time saying what you’re doing and keeping people up to date. You’re using it more like one-way announcements.

Mark: This raises the question of what skills are necessary to succeed inside of Automattic? Because I think there is a little bit of a — with P2 being so central and with written communication being so central and the fact that WordPress.com is a website and a blog hosting platform — that a lot of the most successful elements come around being able to blog internally as well. Do you believe that’s true?

Matt: I try to be pretty active on P2s. Call it an average of maybe a hundred posted comments per month. And my total word counts, I think it’s over a million words now that have been posted to these internal sites. And it’s really one of the richest treasures I have in my time in Automattic because everything is archived, everything is searchable, everything is there. And if I need to remember what I was thinking in 2012 when we made X, Y, Z decision, hopefully that decision is documented and the debate around it, and it becomes this huge source of wisdom, which I think allows the company to evolve in a more informed way. We try to only make new mistakes in having that entire history of the discussions and the collaboration that led to where we are today on these internal blogs. I think it allows us to move faster, smarter and better as we blaze a new trail.

Mark: It raises some other questions about talent. And one of the great promises of distributed work has been the idea that we can find talented people all over the world. But there are also trade-offs to what skills and talents this culture prizes versus, say, an in-office culture that’s more extrovert-focused or verbally-focused. What would you say the major trade-offs are and are they worth it? 

Matt: As I said, different teams work different ways. So there are teams that do very little written communication and communicate mostly through Zoom or audio or things. And so a nice thing about Automattic is whatever your work style is, you can generally find a team that matches that. If you want to be on a team that uses IRC and then basically never has any Zoom meetings, we got that. If you want to be on the team that has daily stand-ups, we got that too. And so by switching teams or divisions within Automattic you can get what might — you might need at a different company to switch companies to find your ideal work and collaboration style.

Q: You have mentioned here if a team wants to experiment with something — what are the experiments that you have maybe heard about recently that we haven’t tried inside of Automattic that you think we really should prioritize and try?

Matt: One that has come up is Invision, which is a distributed company, actually has everyone work East Coast hours. I don’t think that would be right for our entire company. We’re already too distributed for that, but it would be interesting if a team which was largely American-based agreed to overlap the exact same hours, if they would find that beneficial or just inconvenient. 

So that’s how I would want to approach any of these experiments is, say, find a team, at least 10 people, 15 people, who want to try something out, and see how it goes and have them do it for a fixed time period. Do a pre-mortem, do a post-mortem, see what are the learnings from it, and then what are the next actions we want to take from those learnings. 

Q: Is there enough creative tension or friction in a distributed company that maybe some form of self-censorship takes over, or we’re too polite with each other and we don’t raise the questions we need to raise? Do you think that is a valid concern?

Matt: This is why I have become relatively recently obsessed with the idea of an idea meritocracy. Have you read the book “Principles” by Ray Dalio yet? It’s a really impactful one in that you’re not going to agree with it but it will make you think differently. And one of the things he emphasizes is even in their in-office culture that the comfort that people have with challenging ideas and the openness people have to their ideas being challenged is crucial to getting the best outcome. 

Because if either of those is missing you get sub par outcomes. And because when you’re communicating on text it can be so easily misread, people hold back. I do think that’s 100 percent true. It’s less bad on audio or video but definitely in text communication you just don’t have that nuance. All the emoji in the world can’t recreate the kind of timbre and tone of voice and all the additional data we get when we’re actually talking or seeing each other. 

I think a lot about that, and I’ve been thinking a lot about how to foster that. Google talks about psychological safety being key to the high performance of teams. How to foster that where we think that good ideas can come from anywhere and everyone is comfortable presenting and defending vigorously anything they believe in.

Mark: One other thing I’d like to do real quick is just a quick speed round in equipment breakdown. Tell me a little bit about your workspace. Now you travel a lot; you’re in a lot of different cities, tell me a little bit about your must-have items?

Matt: [laughs] Yeah, check out the What’s In My Bag post for the kinds of things I use every single day. It’s the 15-inch MacBook, it’s the cables, it’s the Sennheiser headset for being on calls. I find audio quality is far more important than video quality for creating a great meeting. At home to me that’s the ultimately luxury. [laughs] 

My favorite part from being distributed is when I am able to work from home, which is probably a minority of the year, but I love it because you can have your music you like. I like having a candle on the desk. [laughs] I like the temperature to be a little bit warmer because when I work my hands and feet tend to get extremely cold for some reason. Normally they’re fine but for some reason when I’m on the computer they get ultra cold. I recently installed the instant hot water thing at home. So in my sink I can get near boiling water and make tea. On my desk I always have a notebook. I love paper notebooks for writing things down, I find it’s a lot less distracting than trying to type things out. 

For a while I used to try to have desktops, like an iMac, and in fact the new iMac Pro is — I still have one of those in Houston. But I’ve really gone to where I like a great monitor, [and plugging] it into the 15-inch is the easiest. And I love these new ultra wide monitors. LG makes them. I think I have one that’s 34-inch and one that’s ginormous, 38 inches wide and curved. And using that, it feels like a panoramic experience. 

I knew that I was spending too much time on Google Sheets when I was like, “Oh my goodness” and I stretched out the sheet all the way to the 38 inches of this ultra wide monitor. I was like, “I can see everything!” It felt almost omniscient. But I was like, “I’m in spreadsheets too much.” [laughs] I need to load up some JavaScript.

When I’m at home, I use a Logitech BRIO camera, which is a high-end, 4K-webcam that they have. I find it has a much better aperture so it creates better colors and light in low-light situations, which is often where it is. If I don’t have good natural light wherever I am, I have some desk lamps — just soft light that I can put there so I don’t look weird or back-lit [laughs] wherever I am. If I’m on video I try to — I actually think of it probably much like a webcam YouTuber would. Like, “What’s the lighting like, what’s the audio, how can I present well there in a professional manner?” And I actually see a lot of folks at Automattic curate their background, having things they like in their background. Because you actually end up looking at yourself, what’s behind you, a fair amount when you’re on Zoom or Hangouts or one of these things.

Mark: A couple quick speed round items. Phone calls, love them or hate them?

Matt: It’s actually a resolution of mine to pick up the phone more. I don’t really receive phone calls because it’s all spam now but I love all the non-phone things, like Facetime audio, Zoom, Slack Audio is actually really good. And one thing I’m trying to do more is actually switch mediums. So if I’m finding I’m having a long text conversation with folks, I try to balance the audio. 

And it’s also nice in that some folks — my mom is getting older and sometimes it’s hard for her to read the text. So it’s always really nice to hop onto that. Video is really nice too. I got my mom one of these Google home devices that had a built-in camera. So you can use Google Duo — that’s actually the only reason you would ever use Google Duo to make a video call — to her and it lights up this device that’s by where she usually hangs out. So I’ve found that’s actually been really, really lovely as a way to drop in and stay connected with a loved one who I don’t see as often as I would like. 

Mark: Final question. Twenty years from now, what percentage of jobs will be distributed?

Matt: You’re turning my questions back on me. I am going to say… Well, I kind of don’t want to say so that future guests can answer this without knowing my answer. I do believe there is a window where distributed companies have a real advantage for recruiting, retention, and everything. That window is probably three to five years before the incumbents really embrace this. 

I then think that job seekers are going to learn to ask more sophisticated questions. So they won’t just say can I work from home or not, they really dive in to where do decisions get made, where the center of gravity for the organization is, can their career advance as much being not where the headquarters is or in a distributed fashion as it would if they were say in Mountain View, at Google. 

And those types of more subtle questions will be the things that — as the internet giants embrace the surface of distributed work but perhaps not the deep spirit — all the things that are currently bundled with that — and startups like Automattic or Invision or UpWork — I guess are we still a startup? But companies like that. The bar will change. I’m looking forward to that happening.

Mark: Thank you, Matt.

Matt: It’s been fun chatting. 

Mark: That was Matt Mullenweg. Thanks again, Matt, for taking the time to speak with us about the past, present and future of Automattic. If you want to read more from Matt, you can always go to his blog ma.tt, and he is also Photomatt on Twitter. Thanks for listening.

VC Arianna Simpson on Distributed Work and the Blockchain

Read more about Arianna Simpson in “Is Remote Work Bull***t?”

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

“Remote Work is Bull***t.”

When venture capitalist Arianna Simpson tweeted this opinion, she never could have guessed the massive response she would receive. In this episode, Arianna has a chance to clarify her thoughts on remote work. Then she explains how “programmable money” on the blockchain could lead to a new world of smart contracts and distributed work arrangements.

The full episode transcript is below.


MATT MULLENWEG: Back in March, Arianna Simpson tweeted an offhand remark that went crazy viral.

“Unpopular Opinion: Remote work is mostly bullshit.”

Arianna had no idea that thousands of people would like the tweet, and hundreds would weigh in with their thoughts, some pushing back, others hailing the blunt honesty of her “unpopular opinion.” As a true believer in distributed work, I naturally had to get in touch with Arianna when I saw the tweet.

Arianna is an early stage investor, with close to 40 investments to date, many of which deal with the blockchain and cryptocurrency projects. I wanted to find out: How is it that someone, who knows so much about distributed software that’s created among globally-distributed teams, has such a pessimistic view of distributed work?

It turns out, as it often does, that Arianna’s thoughts on distributed work are more nuanced than her tweet might lead you to believe. We discuss her reservations with remote work, we cover some of the things that traditional office arrangements are really good at providing workers, and we explore how companies can give their employees the best of both worlds with a hybrid model.

But things really get cooking when we started talking about how the blockchain could one day be used by distributed companies to pay workers in far-flung locations with stablecoins that are pegged to a traditional currency. When money becomes programmable, all kinds of interesting contracts and financial arrangements open up, making it easier than ever for the distributed company of the future to partner with workers all over the world.

ARIANNA SIMPSON: My name is Arianna Simpson and I run a fund called ASP. I’ve been an investor for the past several years, first general VC, and now running a crypto-specific fund.

Matt: So you’re into distributed systems.

Arianna: I am.

Matt: One of the reasons I really appreciate you coming on — and a goal of this podcast is — I wanna have the very best versions of why people should be in the same place, as well as making the case for distributed work. We are obviously in the same place right now.

Arianna: Yes, we are.

Matt: We are in a tiny studio in New York City, and this is nice, right? Because we’re having a higher-fidelity communication.

Arianna: Mhm.

Matt: This all started in a tweet. Do you remember the tweet?

Arianna: The tweet heard round the world! Oh yes, it was kind of Paul Revere-ish in its quality in that sense.