Looking back over the 2019 run of the Distributed podcast, one is struck by the wealth of insights our guests have shared in each and every episode. We’ve spoken to CEOs, activists, lawyers, authors, and a life coach, among others — a diverse cross-section of people with a deep interest in the future of work. 

Distributed Podcast: Matt Mullenweg Reflects on Distributed Work in 2019. Read the transcript.

Not every guest has shared our enthusiasm for distributed work, and that’s by design. As host Matt Mullenweg says in our 2019 wrap-up episode, having contrarian voices “sharpens the ideas.” 

When Matt began his distributed journey with Automattic in 2005, many people, including investors he needed to impress, thought the practice a little kooky, at best. 

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.” That’s all gone. That doesn’t really pop up as much anymore. 

Automattic’s growth has silenced many doubters, but Matt doesn’t consider it his mission, let alone the goal of this podcast, to convince every investor and CEO that distributed is the way to go. For one thing, Matt believes that companies who refuse to experiment with distributed work — even huge legacy companies — won’t last, as they’d be unable to tap into global talent markets where more people will demand the option to work remotely. 

“I would be astounded, completely astounded,” says Matt, “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.”

With this podcast and website, Matt aimed to create a resource for the many people he meets who are either on the fence or are just starting out and looking to accumulate knowledge about all things distributed work. So we decided to close out the year with a collection of insights from our first “season” of episodes. 


1. Distributed Work Will Change the Labor Landscape 

Upwork’s outgoing CEO Stephane Kasriel laid out an ambitious vision of a future America, one where the high cost of living in major tech hubs has driven a geographic redistribution of workers back to small and mid-size cities. 

So you’ve got a place where [there are] great jobs, great environment, very international, very dynamic, all that stuff, but completely unaffordable to live in. And then meanwhile you just go a couple hundred miles away from here, you go to Stockton, you go to Modesto, you go to Fresno, you go to Sacramento, let alone going in the Midwest of the country, and you have places where it’s extremely affordable to live and frankly it’s actually very nice to live. There’s plenty of beautiful places outside of the Bay Area where you really want to live but there’s no jobs.

It doesn’t have to be this way, Stephane asserts. We no longer live in the industrial era, when labor was inextricably tied to the operation of heavy machinery; new software tools have made remote collaboration an increasingly viable option for all kinds of knowledge work.

While one of our recent guests, Glitch CEO Anil Dash, illustrated the appeal of living in a vibrant place like New York City, Matt posits in our 2019 wrap-up episode that places like New York or San Francisco are vibrant precisely because that’s where the jobs are. And if you could bring economic activity back to cities that have seen population declines over the last few decades, their vibrancy would return — from renewed civic engagement to flourishing schools, revitalized music and art scenes, and, inevitably, cool restaurants. 

While there are plenty of folks like Anil who thrive in places like New York, there are others who prefer to stay close to their families, wherever they happen to be. Matt uses his affinity for his hometown to illustrate the point: 

I don’t know [that] 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. 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.

2. The Future of Distributed Work Will Involve New Tools

In Episode 2, Pluto VR CEO John Vechey spoke with Matt about the importance of high-fidelity communication. We typically rank the fidelity of digital communication with text chat and email at the bottom, audio in the middle, and video at the top. With video, you’re getting verbal information, tone of voice, and visual nuances like body language. John presented the theory that maybe there’s a mode of digital communication with an even higher fidelity than video chat, which could approximate the gold standard of in-person communication. His company is currently working on a VR product that promises just that. 

The quality of communication that you can have in the room, the body cues, the visual cues, the pace of the conversation, the empathetic experience you can get in person is very different than you can get even on the best that video chat can provide. And it’s because video chat — It’s like, you don’t have a “video.” That’s not a human-centered concept, it’s a very computer-centered concept. It isn’t how you experience people. And so if you had those same six people and they were just all holograms around the room and they were indistinguishable from them in the physical world…

John’s vision of the distributed future involves workers having the option to spin up a VR chat as easily as they set up an impromptu Slack channel today. 

But perhaps we need not look so far ahead to the future of distributed collaboration tools. In our wrap-up episode, Matt reminds us that even workaday tools like calendars still have room for improvement. 

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. 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… 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.”

John Maeda, a former Automattician and now Chief Experience Officer at Publicis Sapient, was also feeling down on Slack in Episode 6

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 this is the real reaction. You can’t tell. 

Although Slack still rules inside Automattic and across many distributed companies, Matt revealed in our wrap-up episode that he’s beginning to feel that Slack might be generating more problems than it solves, although the problem may not lie with the technology itself, but rather the ways in which companies approach it. 

2019 was the year where I felt like — 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 in to Slack all the time, do not disturb notifications, not needing to reply. That just resets that a little bit more for us. 

Whether or not Slack remains the dominant chat platform for work, the tools we use today will need to adapt as a bigger variety of companies embrace distributed work. In Episode 11, CEO Stephen Wolfram talked about how his company, Wolfram Research, builds many of the tools that they use internally. 

“I’m going to start a company that builds the tools that I want to have for myself and that I perfectly well know are going to be useful to lots of other people in the world,” he says. This is a common theme across many Distributed conversations: companies building the tools that they needed because they don’t yet exist. 

3. Distributed Workers Need to Feel Connected

Entrepreneurial coach (and Buffer cofounder) Leo Widrich joined us for Episode 7 and shed some light on the ways isolation can affect the brain. The vagus nerve, Leo explained, governs social engagements, and if not sufficiently exercised, it atrophies. This atrophy can result in what Leo calls the “loneliness spiral.”  

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 of a family, go be with other humans.” 

Fortunately, frequent meetups, coworking spaces, and non-work-related chatter can alleviate the isolating effects of remote work. Matt believes that friendships both inside and outside of work can also help. 

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.

Matt also encourages remote workers to experiment with coworking spaces in order to befriend and learn from folks who can be spatially close, even if they work for different companies. 

4. Distributed Companies Will Benefit by Embracing Diversity

One of the main advantages to distributed work is that it opens up the company to potential employees beyond those that fit the average knowledge-worker profile. Geographic diversity can beget diversity of other kinds, and allows the organization to benefit from the variety of perspectives that come from folks who grew up in different places, with different racial and gender identities, and with different abilities. 

Upwork’s Senior VP of Engineering Han Yuan expressed the benefits of “actually interacting with somebody who isn’t very familiar with how you do things” in Episode 5.

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.

Episode 13 guest Lydia X. Z. Brown, a lawyer and activist among many other things, described a good way to make distributed work accessible for neurodivergent people like them.

When people ask me, “How do we then design a workplace that best fits people with physical disabilities versus best fits neuro-divergent people?” my response is [that] there is no one size fits all. So for example, in the autistic community, there are some autistic people who I know who need to have daily access to natural sunlight, and quite a lot of it, in order to function well. And if the room is closed off and there’s no windows or there’s very few of them, and it’s only artificial lighting, that can make it incredibly difficult to function, let alone to get work done. And at the same time, I know many other autistic people for whom the sunlight is actually physically extremely painful and being around sunlight is emotionally draining, it is sensory over stimulating, and it physically just hurts. 

For Lydia, the question isn’t so much “How do we design a workplace or one methodology of supporting employees in terms of infrastructure,” as it is “How do we make sure that each person that is involved with our company or our organization or our community is able to access the type of environment and space that works best for them.”

5. Trust and Strong Feedback Loops Fill in the Gaps

Feedback is a subject that popped up across many episodes. Strong feedback practices can prevent employees from feeling as though they’re working in the dark. Cate Huston, Automattic’s Head of Developer Experience, cited an ability to receive and respond positively to feedback as an indicator of an employee’s growth potential. 

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. 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.

John Maeda also called out feedback as an essential part of collaboration for distributed design teams. 

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.”

John also says that sometimes direct, brutally honest feedback isn’t always useful for some employees. Some struggle with receiving feedback, and John emphasizes values like empathy and gratitude to temper feedback that an employee might have difficulty receiving. 

In Episode 9, Scott Berkun explained how giving distributed employees the benefit of the doubt helps set the right foundation for a manager and their reports. “I wanted to start off by trusting everyone and extending trust before I ask them to trust me,” Scott says. He explains that receiving feedback is hard because people who are passionate about their work tend to conflate how their work is received with their worth as a human being. He tries to express as much trust in his reports as possible:

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? … 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.

6. IRL Matters

In Episode 15, we joined Automattic in Orlando, Florida, for the company’s annual Grand Meetup, where we spoke to a bunch of folks about what distributed work means to them. We found that while Automatticians deeply value the benefits of asynchronous remote collaboration, they also appreciate the importance of meeting IRL (In Real Life), face-to-face. Division lead Josepha Haden sees it like filling up a social meter that depletes over time. 

When you work in a distributed company, every time that you interact with your colleagues via text… you are taking out of your social bank account with them. So when you get people together, that’s when you have the opportunity to see each other face-to-face, and remind everybody that you’re all human beings. And fill that social capital back up because it’s so hard to communicate via text.

Happiness Engineer Will Brubaker says that the Grand Meetup is a time to get answers that guide him when he’s back at home, and inspire him to work harder. “I’m empowered now to fix the things that have exhausted me,” he says. “And we’re going to start over, and we’re going to move towards the next year’s goals, and I’m very clear what those are. And that’s what this does for me. It’s a reset. It energizes.”

Meeting in person is a chance to engage in a higher-fidelity form of communication. Clark Valberg, the CEO of InVision, expressed the value of face-to-face communication in Episode 14. He explained how we build mental models of the people we interact with, and how spending time in person enables us to increase the fidelity of those models. 

So when we’re online you get to a certain level of precision. [I can] take a long time to get to know you as a person and get to know how you behave and act in different contexts, how you react to certain things as individuals or as groups. When we get together, the fidelity of that model increases exponentially. And we take that mental model into the online environment. That’s the reason for the on-site, in-person experiences.

7. Onboarding Sets the Foundation for Distributed Culture

Maintaining a strong company culture is no easy task for a distributed company. Some of these companies go to great lengths to communicate their vision and values to new employees during long onboarding programs. At Glitch, new hires spend a couple of weeks at the company’s headquarters in New York, learning the ins and outs of their new work environment. Each of them meets one-on-one with CEO Anil Dash to ask any questions they might have. Anil shared Glitch’s process with us in Episode 16:

They get to see — a new employee on their first day — how we share gratitude to one another within the company, and they get to see a meeting where everybody is dialed in, in the same way, whether they’re remote or not. And they get to see us model the behaviors of what we are in the first day, and then they spend some time getting two-factor all set up and all that other annoying stuff. [laughs] Typically the rest of that core onboarding process — and this varies by team — we do a big overview of how the business runs, what the mission is, what the history of the company is, what our goals are, what the road map is.

Whether or not a company has an HQ to host onboarding sessions, meetups can help fill in the gaps. Several of the folks we spoke with at Automattic’s Grand Meetup remarked that they weren’t sure if they were going to fit in until they attended a Grand Meetup. When they were able to witness the company culture firsthand, they understood what made the company special, and gradually learned to find their place within Automattic. 

8. Distributed Companies Should Learn from One Another

In our 2019 wrap-up episode, Matt says, “I’ve definitely been challenged and learned new things every episode.” Distributed work is so new, but a culture of shared knowledge will help push it forward, accelerating its growth and expanding its breadth across the globe. Matt describes his vision for the podcast as an opportunity to share such knowledge. 

There are more and more distributed companies than ever, all over the world, many whom 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… Just having that point of reference for how other companies do it, and what are the best practices they can take away from it.

The understanding that a rising tide of knowledge lifts all boats has driven the creation of the Distributed podcast and of Distributed.blog. We hope you’ve found both to be helpful and engaging so far. We’re excited for what’s to come and hope you’ll join us again in 2020. Thanks for listening and reading. See you next year!

Leave a comment

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: