Episode 17: Matt Mullenweg Reflects on Distributed Work in 2019

Read more of our 2019 takeaways in “Eight Lessons from the Distributed Podcast So Far.”

Distributed Podcast: Matt Mullenweg Reflects on Distributed Work in 2019.

To close out the year, our host Matt Mullenweg is joined once again by Automattic’s Mark Armstrong to discuss the state of distributed work as we transition into a new decade. Matt discusses his key takeaways from his 2019 conversations on the podcast, and reflects on his year as the CEO of a growing distributed company. 

The full episode transcript is below.

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MATT MULLENWEG: Howdy, howdy. Here we are. We made it: the last episode of 2019. The finale of our first season of the Distributed podcast, with me, Matt Mullenweg. 

We’re currently in the thick of planning a fresh slate of episodes for next year. We’ve got the first female 4-star general in the U.S. Army, a guy who grew up in a family of Argentinian sheep ranchers and now runs a distributed blockchain company. Business leaders, thinkers… I’m really excited for next year overall. 

But December is also a great time to reflect. So that’s what we’re going to do now — reflect on some of the great conversations we had in 2019 and talk about where we think distributed work is headed in 2020.

Today I’m joined once again by my colleague Mark Armstrong, who works on a bunch of editorial things at Automattic. He’s been very involved in developing this podcast from day one.

MARK ARMSTRONG: Hey Matt, how’s it going?

MATT: Pretty good, pretty good. It is the end of the year so it’s exciting. I’m actually on my support rotation this week so if anyone contacts WordPress.com support they might get me.

MARK: Yeah, feel free to take a break from this interview to do some live chats if you need to jump in there. [laughter]

Well, Matt, thanks again for having me on. I have been enjoying the podcast all year and I am curious to understand some of your takeaways from the interviews on this podcast. And also, it’s been a big year for Automattic itself, so [I’d like] to understand a little bit about how the changes at Automattic have changed how we work as well.

But first I want to go all the way back. I want you to tell me a little bit why you wanted to do this podcast in the first place.

MATT: As we were scaling Automattic — and continue to scale — I meet and interview a lot of really fantastic leaders — in technology, outside of technology — who don’t know how the distributed thing works. And they have a ton of experience leading teams, running products, etcetera, but not in a distributed manner. 

And so it’s combined with two things happening. One, there are more and more distributed companies than ever, all over the world, many who we’ve had on the podcast already, a lot who are coming up, that were showing that it works and that you could create a world-changing, ultra-competitive company without even a single central office.

And two, there weren’t as many materials or information for how to run something larger than a small team or a freelancer but smaller than the whole thing. I guess the target audience for me for this [podcast] is really managers. People who are managing maybe for the first time, maybe for a long time, distributed teams. Just having that point of reference for how other companies do it and what are the best practices they can take away from it.

I also hope that people at Automattic are listening to this. [laughs] Many of our colleagues are people who are in this very situation. And the first line of our creed is “I’ll always be learning,” and so I hope that people have been learning from this because I know I certainly have been.

MARK: I think it helps clarify what we think and what we believe about how we work, day in and day out, just hearing the other perspectives from the other companies and the other executives or product people within those teams on how they work similarly or differently from us has been hugely helpful.

I think you hit on another point too, which is a lot of the remote work materials that are out there right now are very much about selling the lifestyle versus looking at the reality of what’s happening inside. Do you find that’s the case?

MATT: The lifestyle is definitely part of what I think attracts people to it. But it’s not the lifestyle people expect. It’s more about autonomy, control. I think sometimes people get this idea of Remote Year or something where people are in a different city every other day or every week or every month. And very, very few people who do remote work actually work that way, which is interesting.

MARK: Yeah. Now you very intentionally avoid using the term remote work in favor of distributed work. Can you explain why that is?

MATT: Well, “remote” is appropriate sometimes. It’s also a little bit — it rolls off the tongue a little easier than “distributed.” But I think what we are trying to build at Automattic and many other companies we talk to, is a truly distributed organization. So “remote,” even the word itself, implies that there is a “central” — a bunch of people in one place and there’s a few people who are remote.

When you’re building a truly distributed company, you want to have all nodes on the graph to be equal. So for no one to be remote, for everyone to be equally participating. I would say even if you have an office, and technically you could describe people who aren’t there as remote, you don’t want them to feel remote, right? Almost no one has ever said “Oh, I hope I feel more remote today.” They want to feel connected, they want that equality of interaction and inclusion. 

So that’s really, really important for everyone who’s working with anyone not physically with them to make them feel included. And I think the more we can get away from the term “remote” the more we can help people feel included.

Another thing that has really changed for Automattic is we have gone from around 800 people to closer to 1200 people, so it has been a year of big growth. And of course with the acquisition of Tumblr, we acquired a company which had a very strong presence in New York City, and in fact we now have a pretty substantial office in New York City. 

If you listen over the course of the year, before and after that, I started asking a lot more questions about hybrid organizations where they’re partially distributed and partially in-office, and what the best practices are for that. And something fun for me in the podcast is just being able to ask really, really smart, experienced people what’s on my mind and what challenges we’re facing. And that is something that’s been a new challenge and new learning for Automattic this year.

MARK: Yeah, I think it’s been fascinating. So this was an acquisition that went through in September, Tumblr joining Automattic, and close to 200 plus employees joining Automattic. So that is a big influx of employees that even within a fully distributed organization can change the culture. But now, on top of that, you’ve got an actual office in New York City in which they’re working in that culture.

It has only been a couple months so far but what have you learned about the merging or not merging of those cultures?

MATT: It has definitely taught me that we can’t take anything for granted. It actually made me think how much more important the Distributed blog and this podcast are because things that I haven’t thought about for years are — like how best to do calls or conference calls or meetings or things like that, that are inclusive of remote folks and people who are in the room, are not always widely known and might not even be widely agreed on. This is why in the episode with Anil Dash this came up pretty well, it also came up pretty well in an episode with Merritt from GitHub. So these topics that you’ll hear throughout some of the different episodes, both past and future. 

It made me also realize that culture is so much more than what goes on in an office. It’s really the sum of what everyone does all the time — all those little decisions, the way people communicate, the way people text, expectations for how you reply to things, how meetings happen. Meetings are such a huge part of it. It’s what people are doing when no one else is looking that really makes up culture. 

And it’s something I’ve always subconsciously missed is thinking that there’s more culture in an office. I wouldn’t say there’s more, there is just a different culture in an office. It’s a culture of that ambient intimacy, a very different type of connection that develops between colleagues when you’re in person versus when you’re not. And it has been so long since I’ve closely interacted with an in-person team that I hadn’t really thought about a lot of those things in a while. 

MARK: Are you doing that now with the Tumblr team? Do you pay many visits to the office? What is your plan around that?

MATT: Yeah, I’ve been trying to make it into their office really whenever I’m in New York City. And that has been really great to be able to make one of those connections. I have also realized that they were a hybrid organization even before they joined Automattic. So they have some great colleagues in Dulles, in Richmond, in LA, in Seattle, and some folks just kind of sprinkled all over the country and the world, so that’s also been really great. 

I feel like those people have taken extremely quickly to some of the things that Automattic does, including things like P2, and that’s been pretty exciting to watch. Some of our closest integrations have been so far on just the systems side because we’re migrating all the data from Tumblr. It’s billions and billions, maybe hundreds of billions or trillions of posts, and users and things like that that are all coming over. So our systems teams have been working pretty closely together. And I would say systems is also a field or a role where people tend to be very comfortable communicating online. 

MARK: Yeah, a couple big ceremonial moments that I have witnessed from Tumblr joining Automattic is the first P2 post and the entire company joining Slack and the point at which we decided, like, oh these divisions should all be on the same Slack together. I’m sure there were a lot of meetings around that, correct? 

MATT: It actually ended up being a technically driven decision as much as anything where I guess they had maintained their own Slack in the past, and that was a good thing, but it turned out it was going to be hard or even impossible to migrate most of that data, so we were like, “Well the data, the archives can’t come over, we might as well just get everyone on the same thing.” Because we had a lot of overlap already.

MARK: One of the other things you mentioned in the Anil Dash episode that I found fascinating was the concept that when they’re working together in a physical office they’re not really supposed to talk about work. [laughs] Is that something that you think there is a takeaway from that can be applied within Automattic?

MATT: My big takeaway — and we haven’t tried this yet with Tumblr but perhaps we will at some point — is that idea which you’ll hear in the Merritt episode. One face, one voice, the idea that if you’re on a call, if you’re on a Zoom, wherever it is, if you can have each little box, there would be one face and one voice versus a conference room or something like that, it really does make the conversation flow a lot better. 

MARK: Yeah, that makes a huge difference when you’re on a Zoom, and there is also a little bit of FOMO that happens on the Zooms that I’ve been on where there’s a group of people having a good time together, and you’re watching from your silo and feeling like, “Oh that looks like a fun party, I wish I was there.”

MATT: [laughs] But I do think that Anil was very articulate on the importance of building those non-work connections as well. It’s something we try to do. At Automattic teams do meetups a few times per year and once a year we bring a lot of the company, the majority of the company together, [and figure out] how to leverage that in-person time for that connection.

A number of people who weren’t part of the Tumblr team but part of Automattic have been rotating to work on Tumblr, both to help integrate the systems and also just accelerate hiring things. 

MARK: Now in a lot of the conversations you’ve had this season you’ve spoken to what I would call strong founders or people who had the control and the power within the company to shape it into whatever culture they deem best. I think a lot about how distributed work expands beyond very specific companies into this broader movement growing among mid-size and large companies and how exactly does this work when it comes to bringing distributed into a company where maybe it’s a 50-year old company on its tenth CEO? How do you get to a place where those companies really start to get into this?

MATT: It’s funny because companies that old typically have multiple offices so they have a version of the distributed problem already, you know? 

MARK: Mhm.

MATT: What I see is probably the most important thing to unlock is this idea of getting everyone around the table [being] the best way to solve a problem. That assumes being in person and being synchronous is definitely a way to solve a problem, but I see many companies, particularly older companies or managers with experience in older-style companies, see that as the only way to solve those problems.

I do think that there are asynchronous ways and of course non-physically collocated ways that can actually be far superior in many situations to solve many or most problems that businesses face. I don’t consider it my personal mission to switch all companies to be able to do this but partially that’s because I feel that companies that don’t do this will die off. [laughs] So there will be a Darwinian process where companies who are able to tap into the global talent market and work asynchronously and efficiently all over the world. 

That’s where business is going to be and that’s how things are going to expand. Even if you have a coffee shop, if you have any ambitions to have multiple of them, you’ll need to start to expand your culture, expand the way you work, expand the way you collaborate, expand the way that insights move from customers to process to design, to innovation in a distributed fashion. I would be astounded, completely astounded, if five, ten years from now Google, Microsoft, Apple, Facebook, Netflix, the tech giants that we think of, didn’t have distributed work as a major, if not the major, part of the way their employees work together.

MARK: It’s interesting. Also the broader movement of companies, if they are spreading out beyond the bigger urban centers. There’s this tipping point that has to occur as well, and this goes back to another thing from Anil’s episode. We have always compared Automattic’s distributed model to — maybe it’s a Silicon Valley company with a big campus in a boring suburban area of Mountain View or Menlo Park. 

And he’s saying, “Here you get to live in New York City and people want to live in New York City and that’s exciting!” So cost of living aside, there is this gravitational pull of the big, exciting, urban centers bringing people in. So it feels like maybe there has to be a tipping point still for these companies to take that plunge and to get those workers to want to spread out in other places.

MARK: I think that trend and that story will be so fascinating to see play out over the 2020s as well. Because there’s a lot of data that shows pretty much all the job growth, all the economic activity that has happened in America through this incredible bull run has been really concentrated in urban centers. And if you correlate that with things that are happening politically or frustration or — there’s all sorts of things that could be correlated with that economic activity.

When you start to spread that economic opportunity throughout America, throughout the world, [think about] how that changes those centers. Part of the reason New York is one of the best cities in the world is it’s a center for so many different industries. There’s great jobs there that support great quality-of-life things — great arts, great restaurants, great everything. 

As you start to get more of that economic abundance flowing to other places, guess what, that supports other jobs, other restaurants, other arts, other things that people will consider part of a great quality of life — schools, parks, etcetera — in other places as well. And in fact, places where you might not have the problem of San Francisco being on a small peninsula, Manhattan being an island, you know, the kind of geographic constraints that you do in some of these urban centers. 

MARK: Thinking about this on the broader scale, should there be a government role in promoting distributed work? I feel like we see some novelty initiatives, like Vermont’s remote worker program, where they’ll give people $10,000 to move there. Have you thought about what city, states, and government should be doing? 

MATT: They absolutely, crucially should be doing programs like Vermont’s. If you think of the brain drain problem, where some of the smartest, most successful people leave where they grew up, which has also economic implications and everything, anything you can do to bring those people back is huge. Economic incentives are definitely one way. I think that there’s also streamlined regulation. And then finally, just incredible broadband [laughter] and normal things you would invest in, in a city, to make quality of life good, like great schools, I think are really, really powerful.

And we see it so much with our colleagues — people like to move back to where they’re from and where their family is, and that can be such a powerful thing. I don’t know if I were coming from scratch to America and looking at the top 20 cities if Houston would be at the top of my list to live in. [laughs] But because I’m from there I have such a connection to the place. I grew up there, it’s a formative part of my history. My oldest friends and family are there. It kind of beats out every other place in the world because of those things. 

Because I can get cool music, cool food, cool other things that you can get in New York, San Francisco, etcetera, I can get that in Houston but I can’t get those people [elsewhere]. So I think that draw of where you’re from could be great to reverse the brain drain that happens very naturally all over the world and all over America.

MARK: Are there moments from this season and in conversations with other companies and with our own Automatticians where you think to yourself, “Wow, we are doing this part all wrong?”

MATT: [laughs] That’s a good question. I’ve definitely been challenged and learned new things every episode. We could almost go through them one by one. But even some of the more out there stuff, like John Vechey talking about how they’re collaborating over VR. That just got me really, really excited about how much better than the gold standard today — which is probably Zoom — we could have, to connect and feel presence with each other. 

I really enjoyed our episode, episode four, where we dove into some of the history. Leo Widrich, talking about the downsides, the isolation of distributed work. His and Arianna’s episode, talking about the downsides [of distributed work], I really like those as well, and I hope to have some more of those in the next season where we talk about people who do not agree with this. Because I think that that actually sharpens the ideas quite a bit. 

Stephen Wolfram kind of blew my mind. I don’t know if you remember that one?

MARK: Oh yeah. He has been doing this for almost, what, 30 years plus? What were some of the lessons from that conversation? 

MATT: One of the things I took away from that is the investment — making the internal tools, which also makes me think there is an incredible business opportunity to create tools which natively incorporate remote people and distributed people much, much better, because a lot of the stuff for running companies currently doesn’t. Even things like Google Calendar, which still has meeting rooms built in, and things like that. You could imagine the next generation of this being so much nicer for getting people together.

If you’re in an office, you could walk around and pull five people into a meeting. The distributed version of that is kind of tricky. You end up Slacking each other and trying to pick a time and things like that. And Automattic is not too bad because people aren’t in too many meetings, so sometimes they can hop on things with a short notice. 

But it would be nice to have a way that pops something up and you can raise your hand — I’m available, I’m not available. And then when you reach some quorum of people who need to be at this thing, you can all just immediately hop on a call or something. And making that a little more ad hoc and on demand versus everything having to be so pre-scheduled, which sometimes can be tricky. 

I think a lot about speed of iteration and anything that introduces any lag time into particularly decision-making slows companies down. And you really start to look at places that are moving slower than they need to, you often find these little things, these little one-day, two-day delays that just add up to be weeks and months and then eventually years of things moving slower than a more agile team would be able to.

MARK: I recall you’ve called that chess by mail in the past. 

MATT: Yes. Now in an office you can get the opposite problem where it is so interrupt-driven that people can’t get real work done, that deep work that Cal Newport talks about, who actually would be a cool person to get on the podcast now that we mention it. When you have too many interruptions, it’s really, really difficult to get things done. 

MARK: Yeah, it seems like Slack is still the main place where an impromptu discussion can happen, but again, it’s got some pros and cons there. This year was probably the first time I started to feel personally some real tension around time zones in Slack, and it became apparent to me that Slack is not the best on the time zone front. What’s your take on how to move beyond that?

MATT: It’s an interesting question because I also feel like 2019 was the year where I felt like for — at least for us — Slack went from being a net contributor to our productivity, to a net detractor. We probably need to do a reset around our norms, around not being signed into Slack all the time, do not disturb notifications, not needing to reply. That just resets that a little bit more for us. 

One idea we’ve toyed around with and discussed before is just every person, regardless of your role, not signing into these real-time communications for the first couple hours of their day. So you’re still working but staying off email, Slack, other things that are more communication-driven and really looking at, “What’s the most important thing for me to get done today?” and really checking that off the list.

MARK: It’s interesting when you talk about cultural norms. Cate Huston from Automattic talks a little bit about autonomy, and the choose-your-own-adventure nature of some of this work, or how different teams work. And I wondered, should we be asserting ourselves more to new employees when people come in pushing the Automattic Way? I think it has been great in terms of people coming in and being able to define what works best for them and their team, but I also wonder whether some of the things that have previously been proven to work have been maybe not completely bought into.

MATT: One hundred percent. And that is something — we’re going to make a lot of changes to Distributed.blog next year, and I’d like to get some — almost like some free manager courses. Maybe we can use the Sensei plugin for WordPress. 

Also, Automattic could be 100 times better at this. I was really impressed with some of the stories of how Glitch, how InVision, how others do onboarding, for both new employees or periodically bringing existing people through things. 

Training is an area where we’ve only scratched the surface. And actually one of the hires I’m most excited about that we made in 2019 at Automattic was our new Head of Learning and Development, Michael Norman, whose learning and development is looking at this problem around onboarding, feedback, skill-sharing — everything to do with knowledge, which in a knowledge-worker company is something that I think we could be a lot more deliberate on. 

And, of course, in Automattic fashion, whatever we figure out we will try to open source.

MARK: Excellent. One other big thing with Automattic was Automattic raised $300 million this year from Salesforce Ventures. And I’m curious what fundraising is like when you’re a company with no central headquarters. 

MATT: [laughs] I think it throws some people off. 

MARK: Those coffee shop meetings are a little difficult? 

MATT: Yes, yes. So it is nice to have a dedicated space where you can go — you can bring people into. The reality is also a lot of these things, you’re going to their office. [laughs] But it is nice. There was a time maybe in previous Automattic fundraising when we did have an office, people would come into this empty office and you could almost see it run through their head, “Hey, is this a real company? Is this a pyramid scheme or something? There’s no one here.” So that’s all gone. That doesn’t really pop up as much anymore. 

But for me, I would say the distributed aspect can make it a little more challenging. I spent a lot of time on planes this year, going to those meetings. It also drew me away from the product and engineering work that is my native talent, or thing I’m drawn to, certainly my history with WordPress and Automattic, and it took me away from that a little more than I would like for the year.

But it was super, super important. This fundraising really sets up Automatic’s independence for the foreseeable future and allows us to invest in what I think the opportunity is, and other people agree, is a really, really huge tens-of-billions-of-dollars opportunity out there. It allows us to go for it but the actual fundraising process is one which is, well, just incredibly inefficient in so many ways. And I hope to see things change there more in the future, particularly for private companies. 

MARK: With the fundraising process, did you have a period in the past where you had to spend a lot of that time rationalizing the distributed model compared to this time where it’s more, “Of course, of course you have a distributed team, now let’s talk about the business,” kind of thing? 

MATT: It’s completely changed. So I think both at the high end and the low end. At the high end you have companies, like many of the ones that we had this season — InVision, GitLab, GitHub, Toptal — there’s so many out there that really show — Upwork — an incredible scale. So you’re getting to thousands of employees, billions in revenue often, with the distributed team. So people aren’t really worried at that end anymore.

But the other thing that I think has changed is that folks who work also at the seed level — so invest in seed and series A — and a lot of these investors look at companies both large and small, I’m hearing from investors at that end that almost every company is, if not doing a distributed model, then a hybrid model. So maybe the founders are in San Francisco. 

And by the way, if you’re a founder or a CEO, I do think you need to be where the other companies in your space are, or where the funders are going to be or things like that. So there is going to be a lot of time in those clusters of those things — technology clusters in our industry that you’ll need to beat. But they are not hiring in the Bay Area anymore and they’re not even trying to. 

If you draw that line out a few years, there’s going to be 10 or 100 times as many fully distributed, ultra-successful, large-scale companies five years from now than there are today. And that is exciting. 

And one of the things I wanted to do on Distributed.blog is have a company directory that talks about a few public stats about the scale and approach that some of these companies we have mentioned and had on the podcast have taken, and then of course if they have been on the podcast we can link to it. That I think will be dozens of companies today. And at some point we’re probably going to need to retire it over the coming years, it will just be too many.

I also like it as an idea, though, as kind of a no-fee jobs board. There are some jobs boards dedicated to the distributed work, but I think just the links to the companies, because all companies have hiring pages, could be kind of a nice thing for people who are looking to switch to work in one of these. And then to the extent that the founder or CEO or HR person or someone from the company has been on the podcast, what a great way to learn about the culture and approach of the company.

MARK: Speaking of jobs, what are some tips, what’s a script for people to use if they want to, if they are out job hunting, and they want to make sure they’re building in remote work as a piece of their job? I feel like a lot of distributed work in the future is going to be driven by worker demand, which is insisting that remote work is a piece of what’s available to them, or flexible work. What are some tips that you have to bring this up in the hiring process?

MATT: One tip I do give, sometimes we see people for whom the bulk of their application is that they want to be remote. And that’s not really compelling on the other side of the table. [laughs] This is just general advice for applying for anything. But if you can make your application about why you’re excited about the mission of the company — the products, what you feel is your unique contribution to the products, and the mission and the vision for where the company is going, your experience with a technology stack or their products, or you’re a user, how you supported it. Those sorts of things. 

So if you can really personalize the application — I hate to say it, but that would put you ahead of 95% of applicants. You’d be surprised how much of applying for a job is very much spray and pray, where people are obviously just sending out their application to dozens, if not hundreds, of people or companies without much personalization.

Some of my favorites for applying for Automattic is when people actually make a WordPress website and they make a little mini website about their application or about wanting the job. In fact, we had a colleague of ours, Dave, who was previously a designer at Automattic and then reapplied, and I think he must have known that because he made a website for his reapplication. So in addition to his going to the top of the list because he was an awesome colleague before, it showed that he wanted the job. And that really means a lot.

There’s some advice, if you’re in an in-office job and you’d like to have some more flexibility, that I might have first read in Tim Ferriss’s The 4-Hour Work Week, which was forever ago. But first, be amazing at your job. [laughs] If you’re clearly one of the highest performing people on your team, I think that gives you a lot of built-in credibility and currency. 

And then talk to your boss, your manager, about maybe taking a day a week. And once you get that permission, make sure that day you work even harder than the days you’re in the office, so that it’s really, really clear that there is no downside to the company. If you’re not really respecting the work part of remote work, it can ruin it for your team or the whole company, where people start to associate it with slacking off. 

So if you can set a good example there, and make sure to hold any colleagues accountable — that if they aren’t going to be in the office, they need to contribute just as much if not more — that helps a lot for warming up organizations to be more inclusive of that non-in-office approach. 

MARK: I want to go to InVision CEO Clark Valberg and your episode with him, talking about the mental models that we build of the people we interact with and how face time helps us increase the fidelity of those mental models. Have you ever been in a situation where you’re having a conversation with someone, text, audio, or even video, [when] you thought they felt a certain way and then, once you meet with them face to face, realized you had the totally wrong impression?

MATT:  A hundred percent. Although, I will say that that comes more from text than audio or video. Audio is actually — particularly when it’s high fidelity, like you’re not on “Can you hear me now, can you hear me now,” it’s a good connection, good microphone like we’re using — you can get so much from someone’s tone of voice, their approach, etcetera. It’s really much higher bandwidth.

[With] text, even the best emoji users don’t always communicate as well, and it’s very easy to bring your own point of view or your own view of how things are going into the conversation. So you might view something as being annoyed or short or curt when it’s not.

So the ability to hop quickly onto an audio call or a video call is really key for compensating for that misreading, which is very natural in text communication.

MARK: I think this is the second time we’ve hit on something where it’s like there is a need for an impromptu call or an impromptu video conversation that is not so rigid in these scheduled Google calendar slots. Whoever solves this will be in good shape.

Going back to Leo Widrich, formerly of Buffer. He talks a bit about isolation, and for me that’s one of those things I read about but I feel like I wouldn’t know if it’s actually impacting me in a negative way because it is such a slow creep when it’s happening. Do you grapple with isolation in your own work and life? 

MATT: I am 16 years into working with people remotely from the start of WordPress, maybe even a little bit before that. So I feel like for me, I have a lot of experience now both developing online relationships — the kind of chatter and back and forth that can help deepen that — but also having a strong social network outside of that. I think that’s very much key.

One thing that can happen really nicely if you’re around people you work with every day and you like them, is that also turns into your friendships and your social network. I think that can be really positive, it can also be a mixed bag. It can make it more difficult to give critical performance feedback or if someone gets a promotion, that can change the dynamics of people who used to be peers, now being managers or responsible for compensation, or whatever it might be. 

It’s really nice to have friendships that are just friendships. Neither of you is economically entangled with the other or reporting to the other or any of those other things that introduce a layer of complexity into human relationships. 

So I encourage everyone, even if you really love the people you collocate with every day, to have that. It’s actually one of the cool things I think about co-working is because you can be physically present with people who aren’t at the same company as you, you can have that, get the best of both worlds, get the people who you like going to lunch with a few times a week, and learn from different companies, but not actually overlap in your work-work.

Now, the one thing I do miss — it’s almost like the opposite of what Anil suggested where he said no talking about work at office lunches. I do feel like the catch-up over a meal with a colleague does get you something in terms of the zeitgeist of what’s going on in their part of the company or the world, which is hard to recreate any other way, part of the reason I find it so valuable to have a less formal catch-up with colleagues.

MARK: To that same point — Automattic: too many in-person meetups or not enough in-person meetups?

MATT: I might have to look at the data to see exactly how many we’re doing. I know that we got to a point where we might have had too many a few years ago and we decided to start dialing it back a little bit. Not in a super explicit way but maybe moving teams from every nine months, from every six months, or even greater cadences than a year to balance out the total amount of travel time that people are doing. But I don’t know, I don’t think it’s the amount of meetups, it’s how you use the time.

MARK: Yes. Several of your guests talk quite a bit about that, in which thinking about the time as a very specific thing, and only addressing the things that can only happen in person versus trying to get a lot of work done, or a specific project that you probably could have done on your own, from your own homes. 

MATT: Where I see teams get negative feedback on their meetups is often where [there] was a mismatch of expectations. If your goal in the meetup is to bond as people and get to know each other better, make that the intention going in, and then everyone is expecting that. I get sometimes that we’re, some people were expecting to have a hackathon meetup and some people were expecting to have a team bonding meetup and the distance between whatever actually happens ends up being dissatisfaction for folks. 

I think that you also need to be explicit about the goals and what you’re going to try, because people, rightly, are taking [time] away from their family and their home, so they want to feel like there is something that they’re getting out of it that they couldn’t have done in a distributed manner. So by being explicit about those goals ahead of time, you also have that conversation about other ways you can solve that problem, things you can do before the meetup to try to address it.

And I think it’s still okay if you try something and it doesn’t work in a meetup. I actually find that people have a lot of open-mindedness to an agreed-upon goal, trying something new, and it’s not going to work 100% of the time, you know? We definitely do this at our Grand Meetups. I tell people, “Hey, we’re going to try a bunch of new stuff this year, it’s not all going to work, that’s okay, that’s how we’re going to find the things that do work and we’ll do them again.” And the things that don’t work, now we’ve eliminated that from the possible solution space and next time we can say “Alright we tried that, it didn’t work, we’re going to try something different to solve this problem.” 

So it’s okay if things don’t work if you have the shared expectation about something being an experiment and what the actual goal was going in.

MARK: Great. Matt, thanks again for sharing your experiences with us.

MATT: This has been very exciting. I also want to take this opportunity to thank you and the team that has made the Distributed.blog website, the podcast just a really, really rich resource. I love reading the posts that Cole and others do for each episode. I get something out of it that actually wasn’t in the audio, which I think is a real testament to [how] we’re trying to make the learnings available to as many people as possible and hopefully shift how work is done all over the world, which I think will be a positive impact on the globe.

MARK: So there is a lot more coming from the podcast in 2020. Matt will be speaking with author Morra Aarons-Mele about what distributed work means for introverted people, Merritt Anderson from GitHub on how distributed work can empower people with non-traditional backgrounds, Ann Dunwoody, the U.S. Army’s first female four-star general on running logistics on what might be the world’s largest distributed organization, Xapo CEO Wences Casares on the future of work on the blockchain, and many more.

MATT: Thank you to Mark Armstrong for joining me today, and for the folks at Automattic and Charts & Leisure who make this podcast happen. Most of all, thanks to you, the listeners, for spending your time with us every couple of weeks. It’s been a joy for me personally to hear our guests’ stories, and I’m honored you’ve chosen to invite us into your device to share them with you. 


We’re going to hear a lot more great stories about the future of work in 2020, and it’s going to be pretty awesome. On the next episode I’ll be speaking with Basecamp CEO Jason Fried about the frantic pace that defines life at many startups, and whether or not it has to be that way, and how distributed work might help to alleviate that pressure. Basecamp, formerly known as 37signals, was one of the pioneers of distributed work and their book, Remote, is still one of the best ones out there. 

I’d like to wish a happy, happy holidays to everybody celebrating this time of year. Thank you for listening, and see you in the next decade. 

Published by Matt

In 2002 I started contributing to Open Source software, and life has just gotten better from there. Co-founder of WordPress, founder Automattic.

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