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

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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-pers