On this episode of Distributed, we dig into the good, the bad, and the karaoke-filled history of Automattic meetups. Before the COVID-19 pandemic, our annual Grand Meetup brought the entire company together for a week. The time spent together — along with team-specific meetups scattered throughout the year — helped us strengthen relationships with our colleagues located around the world. Now, as companies and workers grapple with returning to the office, it’s a perfect chance to consider in-person time as an important complement to the autonomy and flexibility of distributed work.

We spoke with Automatticians about how to stay connected in a distributed work culture. You’ll hear from Toni Schneider, Automattic’s first CEO, Josepha Haden Chomphosy, Executive Director of the WordPress Project, and Nick Gernert, CEO of WordPress VIP, along with a wide range of Automatticians.

The full episode transcript is below and has been lightly edited for clarity.

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MATT MULLENWEG: Howdy howdy. This is Matt Mullenweg, the co-founder of WordPress and the CEO of Automattic, and you are listening to the Distributed podcast, which is back after a – I’m embarrassed to say – 500 day hiatus, roughly. I wasn’t as drawn to do more Distributed episodes last year. One because I got super busy and, you know, 2022 I started running Tumblr directly and WordPress.com.

So, things at work got pretty busy, but also just felt like everyone was doing it. Everyone had kind of figured out the remote and distributed thing. And it was going fine. So like, the reason I started the podcast was done so the purpose, the goal I set out to accomplish was completed.

However, recently there’s been a lot of news about companies who are rolling back their employee flexibility and forcing people back into the office 2, 3, 4, 5 days a week. Sometimes, they might be doing this as a way to lay people off. It’s hard to tell the motivations of some of these executives.

But some, I think, in good faith are saying that they were missing something when people weren’t getting together and that employees that joined during the pandemic maybe weren’t as productive as employees who joined prior. It got me thinking and I started to wonder if what they were missing was meetups.

So there is something magic, some frisson that happens in person, that’s impossible to recreate. At Automattic, we just don’t think that needs to be 52 weeks a year. Just like a little salt makes the dish, getting together in person a few times a year is a key ingredient of Automattic’s culture. So I wanted to share with the world and podcast listeners who are now seeing this pop up after 500 days.

How we do meetups at Automattic and why it’s so key. So, I tapped my colleague Chenda Ngak to gather some stories and best practices from Automatticians of how we do meetups. We’ll also put together some guides on the distributed.blog website, after this episode is up. But please get together. Seeing people is important.

And without further ado, I’ll pass you over to the Chenda.

CHENDA NGAK: Grand meetups at Automatic are the stuff of legends. We paused them because of the pandemic and have slowly restarted smaller meetups over the last year. Meetups have been an important tradition ever since the first meetup in 2006. Now, I’d never been to a grand meetup, so I wanted to hear what it was like from Automatticians who have attended.

I started with Lori McLeese. She leads our global people team from Asheville, North Carolina. I couldn’t think of a better person to give me a crash course in meetups. She’s been at Automattic for a decade, and her team is connected to every Automattician around the world.

LORI MCLEESE: So, the different types of meetups that Automattic are our Grand Meetup, which is when the whole company comes together. Unfortunately, we have not had an all company meetup since the end of 2019 because of the pandemic. However, when we were having them before that, it usually lasted about seven to eight days and we usually held them in September or October, and it was a week when the whole company could get together.

We could learn from each other. We could do projects. We could hear amazing speakers, you know, spend time together, both as teams and with people that maybe you don’t work with on a normal basis and just have fun and build relationships. So, that’s one type of meetup.

A second type of meet up is team meetups, which is very similar to the Grand Meetup, but on a much, much, much smaller scale. So, team meetups are usually anywhere from four to 10 people. The team actually decides where to go, what to do, what type of social activities they want to be involved in.

And as a company, we give them a budget and then the teams make all that decision. And we ask people after their meetups to actually write a summary on our internal, we call it Meetomattic and it’s a P2 or a website where all the teams record experiences of their meetup and actually rate the location about whether it would be good for other teams to go.

CHENDA NGAK: So, for those who don’t know, Lori is talking about an internal network of blogs called P2. The recaps on P2 are like a mini city guide with best restaurants, activities, the team’s itinerary for the week, and the average cost of throwing a meetup in cities around the world.

LORI MCLEESE: And then a third type of meetup is a division meetup, and that’s when several teams within the division get together. And I would say that those depending on the division run from like 75 to maybe 200 people. So, it’s a little bit of a mash up between team and Grand Meetup.

CHENDA NGAK: Why do you think that meetups are so important for our culture?

LORI MCLEESE: While it’s great to work from home, work distributedly, work from anywhere, there is something missing when all you ever have is either text communication or perhaps even video communication and I think one of the best things about meetups is that that’s where spontaneity can occur.

CHENDA NGAK: I wanna expand on that and see if we can talk a bit about what meetups mean for team morale and inclusion.

LORI MCLEESE: For team morale, there is an excitement not only of being at the meetup, but also planning the meetup and talking about what do we want to do together? Whether that’s the work activities or the social activities, and learning about people’s preferences for inclusion. It’s also really important because we have a pre-meetup survey that we ask each attendee to complete as the team members are planning the meetup.

And you know, it’s not just dietary needs, which are important, but it’s things like how far are you comfortable walking? Are you comfortable speaking up in public or would you rather have the questions beforehand? And so it gives you an understanding of people’s work styles, which are very different and helps the organizers to really plan a much more inclusive event.

And those learnings then carry over after you get back from the meetup when you’re working online so that you can remember like, oh, this person doesn’t like to be called out on the spot. They like to have questions in advance so that they can think about it before presenting an answer.

CHENDA NGAK: Now that Lori has explained the different types of meetups, I thought it would be interesting to get background on why we started doing them. So, I caught up with Toni Schneider who joined Automattic in 2006 as its first CEO, just six months after the company was founded.

TONI SCHNEIDER: I think the reason we started having meetups right away and they worked right away is because there was a meeting of the existing team that was already distributed and working together via open source and really liked meeting in person every once in a while.

So, that was already a pattern that was established and in my background, coming from other startups and spending a little bit of time at Yahoo, at a bigger company, kinda seeing if we fast forward this, if WordPress gets huge and we have a huge team, how can we make this work at scale? That’s gonna be different than tho...