Episode 17: Matt Mullenweg Reflects on Distributed Work in 2019

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 US Army, a guy who grew up 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 gonna do now, reflect on some of the great conversations we had in 2019, talk about where we think distributed work is headed in 2020. Today I'm joined once again by my colleague Mark Armstrong, works on a bunch of editorial things at Automattic. He's been very involved in developing this podcast from day one.

Hey, Matt, how's it going?

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

Yeah, feel free to take a break from this interview to do some live chats if you need to jump in there. 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 understand a little bit about how the changes at Automattic have changed how we work as well. So, but first I wanna go all the way back. So I want you to tell me a little bit why you wanted to do this podcast in the first place.

As we were scaling Automattic, as 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, etc., but not in a distributed manner. And so it's combined with two things happening. Um, one, there were 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, um, 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, just this kind of— there wasn't as many materials or information for how to run something larger than a small team or freelancer, but smaller than the whole thing. So, like, especially for— I guess the target audience for me for this is really managers. So people who are managing, maybe for the first time, maybe for a long time, distributed teams, just having that sort of point of reference for how how other companies do it and what are the best practices they can take away from it. So I also hope that people at Automattic are listening to this. So many of our colleagues are people who are in this very, 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.

Yeah, no, I think it helps clarify what we think and what we believe about how we work day in and day out, just hearing— and hearing the other perspectives from the other companies and the other executives 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, selling the lifestyle versus looking at the reality of what's happening inside. Do you find that's the case?

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 like a remote year or something where people are in like a different city every other day and every week or every month, and very, very few people who do remote work actually work that way, which is interesting.

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

Well, remote is appropriate sometimes. It's also a little bit— 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's a central. So there's 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 kind of all nodes on the graph to be equal. So for no one to be remote, for everyone to be kind of equally participating. I would say even if you have an office, And sort of technically, you could describe people who aren't there as remote. You don't want them to feel remote, right? Almost no one's ever said like, "Oh, I hope I feel more remote today." People want to feel connected. They want that sort of equality of interaction and inclusion. So that's really, 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's really changed for Automattic is we've gone from around 800 people to closer to 1,200 people. So it's been a really— a year of big growth. And of course, with the acquisition of Tumblr, we, uh, 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's something that's been a new challenge and new learning for Automattic this year.

Yeah, I think it's been fascinating. So we had— this was an acquisition that went through in September, Tumbler joining Automattic and close to, what, 200+ employees joining Automattic. So this is— that's 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. So it's only been a couple months so far, but what have you learned so far about the sort of merging or not merging of those cultures?

It's definitely taught me that you can't take anything for granted and actually made me think how much more important the blog distributed.blog and this podcast is 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 the episode with Merit from GitHub. So these are 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. Mm-hmm. 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, when, and 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 I think sort of subconsciously missed is thinking that there's more culture in an office. And there, I wouldn't say there's more, there's just a different culture in an office. It's a culture of that sort of ambient intimacy, a very, very different type of connection that develops between colleagues when you're in person versus when you're not. And it's been so long since I've really closely interacted with an in-person team. That, you know, I hadn't really thought about a lot of those things in a while.

Are you doing that now with the Tumblr team? Do you pay many visits to the office, or what's your plan around that?

Yeah, I've been trying to make it into their office as, well, really whenever I'm in New York City, and that's been really great to be able to make some of those connections. I've also realized that, you know, they were also a hybrid organization even before they joined Automattic. So they have some great colleagues in Dulles and Richmond and LA, LA and Seattle, and some folks just kind of sprinkled all over the country and the world. And so that's been also 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 system side, because we're migrating all the data from Tumblr. It's like billions and billions, maybe hundreds of billions or trillions of posts. Users and things like that that are all coming over so that our systems teams have been working pretty closely together. I would say systems is also a, maybe a field or a role where people tend to be very comfortable communicating online.

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

It actually ended up being a technically driven decision as much as anything, where, um, you know, I guess they had maintained their own Slack in the past, and that was, 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're 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.

One of the other things you mentioned, 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, which, uh, what— so is that something that you think there's a takeaway from that can be applied within Automattic?

My big takeaway, and we haven't tried this yet for Tumblr but perhaps will at some point, is that idea, uh, which you'll hear in the Merit episode, um, one face, one voice. Yeah, the idea that if you're, if you're on a call, if you're on a Zoom, wherever it is, you could have each little box there be one face and one voice versus, you know, a conference room or something like that, it really does make the conversation flow a lot better.

Yeah, that makes a huge difference when you're on a Zoom. And there's 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, from your silo and feeling like, oh, that looks like a fun party. I kind of wish I was there.

But, you know, it does. I do think that Aneel was very articulate on just 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, you know, a lot of the company, majority of the company together. You know, how to leverage that in-person time for that connection. You know, for people, a number of people who weren't part of the Tumblr team but part of Automattic have been rotating to work on Tumblr, both help integrate the systems and also just accelerate hiring hiring things.

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 sort of deem best. I think a lot about how distributed work expands beyond very specific companies into this broader movement growing among midsize and large companies. And how exactly does this sort of work, when it comes to bringing distributed into a company where it's maybe it's a 50-year-old company on its 10th CEO? How do you, how do you get to a place where those companies really start to get into this?

It's funny because companies that old typically have multiple offices, so they have a version of the distributed problem already, you know. What I see is Probably the most important thing to unlock is this idea of getting everyone around the table is the best way to solve a problem. You know, 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 most problems. Problems. I do think that there are asynchronous ways and, of course, non-physically co-located ways that can be actually far superior in many situations to solve many or most problems that businesses face. I don't consider it, like, 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. So there'll be a Darwinian process where companies who are able to tap in to the global talent market and work asynchronously and efficiently all over the world, I mean, that's where business is gonna be, and that's how things are gonna expand. You know, even if you have like a coffee shop, if you have any ambitions to have multiple of them, you'll need to start to, you know, expand your culture, expand the way you work, expand the way you collaborate, expand the way that insights move from customers to process to to design, to innovation in a distributed fashion. I would be astounded, like completely astounded if 5, 10 years from now, Google, Microsoft, Apple, Facebook, Netflix, the kind of tech giants that we think of, didn't have distributed work as a major, if not the major part of their, way their employees work together.

It's interesting also sort of the broader movement of companies if they are spreading out beyond the bigger urban centers. There's kind of this tipping point that has to occur as well. And this goes back to another thing from Anil's episode is around, you know, I've always thought about, or we've always compared Automatic'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, well, here you get to live in New York City, and people want to live in New York City, and that's exciting. So there's— so cost of living aside, there's 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.

When I think that trend of that story will be so fascinating to see play out over the 2020s as well, because, you know, there's a lot of data that shows pretty much all of the job growth, all the economic activity that's 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, you know, there's all sorts of things that could be sort of correlated with that economic activity. When you start to spread that economic opportunity throughout America, throughout the world, how that changes those centers. And part of the reason New York's one of the best cities in the world is also has, it's a center for so many different industries. There's great jobs there, there's great, that supports great, you know, other, 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, et cetera, in other places as well. And in fact, places where you might not have the, you know, sort of 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.

Should there be— do you, thinking about this on sort of the broader scale, should there be a government role in promoting distributed work? Like, we see some novelty initiatives like Vermont's remote worker program where they'll give people $10,000 to move there. Have you, have you thought about, you know, what, what cities, states, and, and government should be doing?

They absolutely crucially should have been doing programs like Vermont's. Like, if you, if you think of the brain drain problem where some of the smartest or most successful people leave where they grew up, um, or which has all sorts of economic implications and everything, anything you can do to bring those people back is huge. So economic incentives are definitely one way. I think that there's also sort of streamlined regulation And then finally, just incredible broadband and normal things you would invest in, in a city to just make quality of life good, like great schools, I think are really, really powerful. And we see it so much with our colleagues is that 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 there were— if I were, you know, coming from scratch to America and looking at the top out of 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. Me and my oldest friends and family are there. Like, 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, etc. I can get that in Houston, but I can't get those people. And so I think that that sort of draw of where you're from could be great to kind of reverse the brain drain that happens very naturally all over the world and all over America.

Now, are there moments from this season and in conversations with other companies and with our own automaticians where you think to yourself, wow, we are doing this part all wrong?

Ha! That's a good question. You know, I've definitely been challenged and learned new things pretty much every episode. We could almost go through them one by one, but like, you know, some of the more out-there stuff like John Vecchi talking about how they're collaborating over VR, like that just got me really, really excited about you know, 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 4, where we kind of delve into some of the history. Leo Widrich, I might have mispronounced that, but he talked about—

Leo Widrich.

Widrich, thank you. Talking about the downsides, the isolation of distributed work. And in fact, all the— his and Arianna's episode talking about the downsides, 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.

Oh yeah. So did you— you know, he's been doing this for almost, what, 30 years plus? What were some of the lessons from that conversation?

You know, one of the things I took away from that is the investments, like making the internal tools, which also makes me think there's an incredible a business opportunity to create tools which are kind of natively incorporate people, 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 like meeting rooms built in and things like that, like you could imagine the next generation of this being just so much nicer for getting people together. If you're in an office, you could walk around and pull like 5 people into a meeting. The distributed version of that is kind of, kind of tricky. You end up kind of slacking each other and trying to pick a time, things like that. And Automattic is not too, too bad because people aren't in too many meetings, so sometimes they can hop on things in with a short notice. But it'd be nice just to have a way that like kind of pop something up and you can raise your hand, you know, 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 kind of immediately hop in 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. Anything that introduces any lag time into particularly decision-making, I think, slows companies down. When you really start to look at places that are moving slower than they need to, you often find these little things, these little, you know, 1-day, 2-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.

I recall you've called that chess by mail in the past.

Yeah. Now, in an office, you can get the opposite problem where it's so interrupt-driven that people can't get real work done, that deep work that Cal Newport talks about. Actually would be a cool person to get on the podcast now that we mention it. You know, when you have too many interruptions, it's really, really difficult to get things on.

So yeah, it seems like that Slack is really 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?

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 kind of a net contributor to our productivity to probably a net detractor. And where it's something where there is, we probably need to do a reset around our norms around not being signed into Slack all the time, you know, do not disturb notifications, not needing to reply, that, That just, you know, kind of resets that a little bit more for us. You know, one idea we've toyed around with and discussed before is just every person, regardless of your role, not signing into these real-time communication for the first couple hours of their day. So you're still working, but, you know, staying off email, Slack, other things that are more kind of 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.

Yeah, it's interesting about when you talk about cultural norms. Kate Houston from Automattic talks a little bit about autonomy and sort of 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, you know, pushing the Automattic way? I think it's 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.

100%. And that's something, yeah, 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, like, Automattic could be 100 times better at this. I was really impressed with, you know, some of the stories of, uh, how Glitch, how Envision, how others do onboarding. For both new employees or kind of periodically bringing existing people through things. Training is an area that 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 develop, Michael Norman, who's learning and development, who's really looking at this problem around onboarding, feedback, skill sharing, all 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 Automatic fashion, whatever we figure out, we will try to open source.

Excellent. One other big thing with Automatic was Automatic 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.

Ah, um, I think it throws some people off.

Those coffee shop meetings are a little difficult.

Yes, yes. So, you know, it is nice to have a kind of dedicated space where you can go, you can bring people into. Um, the reality is also, you know, a lot of these things you're going to their office, um, but, uh It is nice. I mean, there was a time maybe in previous automatic fundraising when we did have an office, people come into this empty office and you could almost see it run through their head like, "Hey, is this a real company? Is this like 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, I feel like, drew me away from the product and engineering work that is kind of my native, 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. Now, but it was super, super important. This fundraising really sets up Automattic'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, you know, multi-tens of billions of dollars opportunity out there. So it allows us to go for it. But, you know, the actual fundraising process is one which I think 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.

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?

It's completely changed. So I think both at the high end and the low end. So at the high end, you have companies like many of the ones that we had this season, you know, Envision, GitLab, GitHub, Doctow. 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 a distributed team. So people aren't really worried at that end anymore. But the other thing that I think has changed is that, you know, folks who work also at the seed level, so invest in seed and Series A, and a lot of these investors kind of look at companies both large and small. I'm hearing from investors at that end that, you know, 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 be. But they're not hiring. In the Bay Area anymore, and they're not even trying to. So I feel like that is— if you kind of 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 in 5 years from now than there are today. And that is exciting. And one of the things I want to do on distributed.blog is just have a company directory that talks about, you know, a few public stats about the scale and, and approach that some of these companies we've mentioned and had on the podcast have taken. And then of course, if they've been on the podcast, we can link to it. Uh, 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'll just be too many. I also like it as an idea though, as kind of like a, a no-fee jobs board. There are some job boards dedicated to 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.

Speaking of jobs, what are some tips? What's a kind of script for people to use if they want to— if they're 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?

One tip I do give, you know, sometimes we see people who the bulk of their application is that they want to be remote, and that's not really compelling on the other end of the other side of the table. This is just general advice for any applying for anything, but if you can make your application about why you're excited about the mission of the company, you know, 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 their technology stack or their products. Are you a user? Have you supported it? Those sorts of things. 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, kind of where people are obviously just sending out their application to dozens if not hundreds of people or companies without much personalization. So, 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. And so in addition to his, you know, going to the top of the list because he was an awesome colleague before, you know, it kind of showed that he wanted the job. And that, you know, 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 think I might have first read in like Tim Ferriss' "The 4-Hour Workweek," which was forever ago. But first, be amazing at your job. So if you're clearly one of the highest performing people on your team, I think that gives you a lot of, just built-in credibility and currency. And then talk to your boss, your manager, about maybe taking a day a week. And then 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 that there's no downside to the company. If you're not really respecting the work part of remote work, it can ruin it for— it can really 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 just warming up organizations to be more inclusive of that non-in-office approach.

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

100%. And although I will say that that comes more from text than I would say audio or video, there is something— 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, etc. It's really, really much higher bandwidth. Text, you know, 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, you know, the ability to hop quickly onto an audio call or video call is, I think, really, really key for, for compensating for that misreading, which is very, very natural in text communication.

I think this is the second time we've hit on something where it's like there is a need for an impromptu, an impromptu call or an impromptu video conversation that is not so rigid in these scheduled Google Calendar slots. Um, whoever solves that will be in good shape. One other thing I want to ask about is— so going back to Leo Widrich, formerly of Buffer, so 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's such a slow creep when it's happening. Do you grapple with isolation in your own work and life?

You know, I am 16 years into working with people remotely from the start of WordPress, maybe even a little bit before that. And so I feel like for me, I have a lot of experience now, both developing online relationships, you know, the kind of chatter and back and forth that can help deepen that, but also just having a really strong social network outside of that. And I think that's very much key. One thing that, you know, what 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 social network. I think that can be really positive. It can also have mixed bags, you know. It can make it more difficult to give critical performance feedback. Or if someone gets a promotion, that can change the dynamics of, you know, people who used to be peers now being managers or responsible for compensation or whatever it might be that can just change those dynamics. And so it's really nice to just have friendships that are just friendships. You know, neither of you is economically entangled with the other or reporting to the other or any of those other things that just introduce a layer of complexity into human relationships. So I encourage everyone, even if you really love the people you co-locate with every day, to have that. It's actually one of the cool things I think about coworking is because you can be physically present with people who aren't at the same company as you, you can kind of have that, get the best of both worlds. You know, 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 and do get from is almost like the opposite of what Neil suggested, where he said, you know, no talking about work at office lunches. I do feel like that just kind of 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 that is really, really hard to recreate any other way. So, that is something that I— part of the reason I find it so valuable to have a less formal catch-up with colleagues.

Now, to that same point, automatic— too many in-person meetups or not enough in-person meetups?

Might have to look at the, 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. Um, not in a super explicit way, but maybe moving teams from like every 9 months to every 6 months, or, you know, some even greater cadences than a year. To kind of balance out the total amount of travel time that people are doing. I don't know. I don't think it's the— it's not the amount of meetup, it's how you use the time.

Yeah, several of your guests talk quite a bit about that in which, you know, thinking about the time as a very specific thing and only sort of 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, uh, from, from your own homes.

Where I see teams get feedback, negative feedback on their meetups, it's often where there is a mismatch of expectations. If your goal of the meetup is to bond as people and get to know each other better, like, make that the intention going in, and then everyone is expecting that. I get sometimes that where some people are expecting to have like a hackathon meetup and some people are expecting to have like a team bonding meetup. And the distance between whatever actually happens ends up being dissatisfaction from folks. I think that you also just 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 and everything like that. 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 at 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 gonna work 100% of the time. We definitely do this at our grand meetups. I tell people, "Hey, we're gonna try a bunch of new stuff this year. It's not all gonna work. That's okay. That's how we're gonna find the things that do work, and we'll do them again. And things that don't work, now we've eliminated that from the possible solution space, and next time we could say, 'All right, we tried that, it didn't work. We're gonna 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.

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

This has been very, very exciting. I also want to take this opportunity to thank you and the team that's made the distributed.blog website, the podcast, just a really, really rich resource. I even, I like, I love reading the post that, that Cole and others do for each episode. Like, I get something out of it that actually wasn't in the audio, which I think is a real testament to 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.

So there's a lot more coming from the podcast in 2020. Matt will be speaking with author Maura Aaron Smiley 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 US Army's first female 4-star general, on running logistics on what might be the world's largest distributed organization, Zappos CEO Wences Casares on the future of work on the blockchain, and many more.

Thank you to Mark Armstrong for joining me today. And for the folks at Automattic and Charts and 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 gonna hear a lot more great stories about the future of work in 2020, and it's gonna 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, how distributed work might help 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 everyone celebrating this time of year. Thank you for listening, and see you in the next decade.