How to Throw a Grand Meetup for a Thousand People

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 those big companies. 

And the big companies I saw were, when they were doing meetups, it was really offsites and they were awkward, in my opinion, because people were already spending all day together at work. And they’re like, “How do we have to now go somewhere else and spend even more time?” And they’d be very scripted and all about the product roadmap and all these things. And I knew we didn’t want that at all.

We flipped it upside down and said, what if we had a meetup and did essentially no work, nothing extra, nothing scripted, purely focus it on social time, purely focus it on bonding because that’s what we need more of.

And then we saw things that came out of the meetups that I don’t think would’ve arisen otherwise. And I think that’s why we kept doing them too. Things like P2 came out of the meetup and that became hugely important for the company.

We had town halls and we had flash talks, things like that. I think, are examples of things that just happen when you get together in person and just kinda see what arises for people. WordCamps were another example. You know, the first WordCamp was essentially a brainstorm in one of our meetups and said, “Let’s try it.”

CHENDA NGAK: Do you have any practical advice for startups that wanna throw a meet up today?

TONI SCHNEIDER: Yeah, I think it’s important to set the expectations. And we have to be pretty explicit and say, “No, this is part of the job. This is part of your expectation. You can’t skip these.” And it’s really important to say that up front to people and say, “Look, there’s 52 weeks in a year. You know, you’re gonna maybe work, I don’t know, 40-some of those. And most of that’s gonna be at home and you’re totally in control, but you know, probably two or three weeks a year, you’re gonna participate in these types of activities.”

CHENDA NGAK: Another thing that I was curious about is if you’ve noticed meetups come up in other conversations with any startups that you’ve been working with, or in the tech industry in general.

TONI SCHNEIDER: Oh, absolutely. I mean, I am now with True Ventures. We have ours, a little shorter, usually three days every quarter, four times a year. Most of the startups I work with – we have over 200 in our portfolio. At True, everybody is at least partially remote or fully remote, and everybody’s trying to figure out how to spend time together.

So, it’s on everybody’s mind. I think a lot of people are adopting these kinds of, you know, best practices that fully distributed companies have come up with. I think it’s working. I feel like there’s a whole set of tools in the industry growing up around it. Right? There’s a lot of people going, “OK, we can host some of these meetups and retreats and be a great place for people to get together. We can be a platform where people can organize their meetups.” 

And I think one of the companies we invested in called Happy does that. And there’s a huge demand for it, especially from big companies who are saying, “OK, all of our teams want to meet in person and we’re not set up for it, help us figure out how to do these things.” And I think we’ll just see more and more of it. 

I have friends who are essentially building retreat centers around this notion and saying, we don’t need more hotels. We need more places where these teams can gather and spend several days and be creative together. It’s really nice to be in a place where you feel like, “Oh, it’s just us. We get to do our thing.”

I think all of our initial meetups were like, there was like a ranch in Arizona where it was just us and there was like a bed and breakfast in Mexico where it was just us. And we could bring our Wii and play Wii tennis and be goofy and stay up till two in the morning and nobody cared. And I think that’s important too, to pick venues that allow for that to happen versus again, the more scripted, “Here’s, you know, a place with good wifi and good presentation system.” And let’s all sit in a conference room. We’ve always avoided that.

I see a lot of teams gravitating towards the more retreat type setting. And I think hopefully there’ll be a lot more of it. I think there’s still, there’s a huge untapped market for it because it’s still hard to find something that’s like a retreat, but also has really good internet and you actually can be connected. We would find these places like, “Oh my God, this looks amazing.” “Oh no, we don’t have internet people come here to disconnect.” “Oh no, that’s not us.” We’re gonna be the opposite. We’re gonna get there and you know, 20 or 30 laptops are gonna open and your internet’s gonna come to a halt.

CHENDA NGAK: What do you think our legacy has been for remote companies today?

TONI SCHNEIDER: Yeah, it’s hard to tell, but I always assumed that it’s amazing as WordPress is. I think our long term impact might be just as much that we showed that a remote model can work. I definitely remember the early days and it was very, very different when we tell people that we were distributed. A lot of people didn’t like the idea. 

They wanted to argue why it was a bad idea or they just didn’t think it was ever gonna scale. There was a lot of like, “Oh, that’s great, but you’re just 20 people just wait till you’re 50 people just wait till you’re a hundred people. It’s definitely gonna break at 200 people.” So there was just a lot of disbelief that this actually works. I think we kind of chipped away and it’s not like we started the company to prove that distributed can work. It just worked for us and we thought, well, let’s keep going and let’s make it work even better. And let’s really lean into it.

And just leading by example, I guess, other companies now look and go, “Oh yeah, that’s an option. It’s not the only option. There’s lots of ways to build an organization, but this is a real option. This can work.” We’re 2,000 people now and it’s working and it’s a great organization. So, I really think it has helped tremendously to just make it available to other entrepreneurs and, and be able to say, “Oh look, they did it, WordPress did it.”

It’s funny to think back, but there was a lot of skepticism. We even had employees who would say, “Can you send a message to my parents and tell them that this is real, this isn’t like some weird scam?” Even the employees were like, “I love it, but like my friends and family think I’m crazy.” So, we’ve come a long way. I’m proud that we’ve been able to help this model gain more mainstream acceptance. And obviously with COVID, it kind of kicked into hyper drive and 10 years of adoption happened in like 10 days.

I think all that work of slowly perfecting the model and showing that it works, sort of, at the right time was all available for people to go, “Oh OK, let’s try that.” And then I think the other thing that happened is we had less to do with all the tools that started to become available.

In the beginning we built all our tools ourselves, and then we realized, “Oh, now we can use Slack; now we can use Zoom.” 

I think a lot of companies when COVID hit realized that they were already using all the tools. So, I would give a lot of credit to those companies, as well, for popularizing tools that companies didn’t even totally realize you already have all the infrastructure in place. And I know a lot of companies I worked with were shocked how easy it was to just work from home. They’re like, “Oh wait, we don’t even have to change anything. We just already have it all in place.”

And I think that was huge. So, that lined up really well as well.

CHENDA NGAK: I wanted to hear more about the vibe and social aspects of meetups. So I rounded up a few members of our house band, the Automusicians. There are hundreds of musicians in this group. They discuss songs and set lists on our internal blog system, P2, and then they sign up to perform at the Grand Meetup. I could only get time with Matt, Leif, and Paul who are based in South Africa, Germany and Austria, respectively. Paul works with me on WordPress.com while Leif and Matt work on WooCommerce. 

How does the band prepare for a show when all of the members are distributed?

LEIF SINGER: For me, there’s two things to it, right? The practice week together, where you get to know everyone, you make music together which is just fun and makes people bond. Right. But you’re working towards this goal, which is the last evening, and that is an evening where you get to be a rockstar for one day a year.

PAUL BONAHORA: I guess everybody managed it differently, in their own way, but I recall there was like a spreadsheet where we would put in who would want to practice. Because we had a couple of practice rooms. There were two or three, at least at the one meetup that I’ve been to two of them.

And there was a spreadsheet where everybody would book their slot. So, we had these practice slots where the band would show up for their practice slot and we would get to get the instruments and just practice the songs, which would be a really cool way to bond.

CHENDA NGAK: I would love to hear more about the vibe of a Grand Meetup.

MATT COHEN: Yeah, there’s, there’s definitely an energy to it. Compared to a smaller team gathering of five to 10 people. That’s one thing. Coordination is really straightforward there. You’re all kind of in the same room or nearby to each other. At a big event, like a Grand Meetup, there’s several hundred people. Maybe even a thousand people or more.

It’s electric, you’re not always seeing people that you work with day to day. I think most times you’ll actually see a lot more people that you don’t often see, which is somewhat intentional in some contexts like around meal time and things like that.

But it’s nice to embrace every aspect of the meetup as an opportunity for that kind of connection. So, standing in a buffet line at a meal, for example, and you look across the table and you see someone you haven’t seen in three years, who’s now moved to a different division in the company and you say, “Oh wow. So nice to see you. How are you? How’s your kids? How’s, you know, how’s life on your end of the world?” You know, being that we’re in 90 plus countries as well. It’s powerful.

LEIF SINGER: The magic starts even at the airport, like, especially coming from Europe, for example. There’s usually one or two hubs that basically everyone goes through.

So, as I have headphones on at the airport, I listen to music and I walk to the gate from my previous flight and I sit down. And then suddenly I realize I sit among a dozen other colleagues whom I can identify through their backpacks with WordPress logos and stuff. Right?

And, they’re like, “Oh, you probably belong to us. We have never met before, but ‘howdy.’” 

That’s where it starts, right? And then you start to see other people trickle in that, maybe you’ve worked with before that you’ve met. And then you have these, “Oh, we haven’t met in two years. How you been, good to see you again.” Then after the full day of travel again, coming from Europe, when it’s usually in the U.S., there’s like 10 hour travel and quite some time zone difference, right?

So, when we arrive there at, say 8:00 pm, we’re super tired, but there are so many people from the events team, welcoming everyone. It’s such a buzz in the air. Like you feel instantly welcome and among friends. That’s super touching.

PAUL BONAHORA: Yeah, I can totally relate to that feeling of getting excited there. And then after being on the plane, you know, for 10 hours that kind of simmering down, but then going back up when, when, once you get to the venue and you start meeting more and more folks, so it’s very energizing.

CHENDA NGAK: What are some of your favorite social moments from previous meetups?

MATT COHEN: It’s tough to pick just one. The two that jumped to mind and I’ll go through them individually. But the first one was those ad hoc moments where you’re all just sitting around and having a discussion about something, but it’s a very deep discussion. And then also at the recent GM, the activities around mindfulness and breath work and, and meditation, and things that are less tech, but still extremely important. Right? Those two really stood out to me.

The sitting around at a table, there’s so many spaces in a, in a hotel or a resort for those impromptu connections. And I think we’ve done that really well at GM’s overall, is creating those spaces. Whether it doesn’t have to be around a bar or a restaurant, it can be just couches in the hotel and just finding those nooks and saying, well, let’s have a deep discussion about the one that comes to mind is the history of Scotland, for example and common law in Scotland. And that is a completely random subject that would’ve never come up if it weren’t for the people at that nook, at that time.

And that really stands out and you, you know, you carry that through. In building the connection with that other person. It’s not about the topic necessarily, but it’s a way of creating that bond, right. That, that really stands out to me. It’s purely social.

LEIF SINGER: My immediate thoughts go to big events, like for example, the closing party or the silent disco was always really, really great. I usually don’t dance, but that is a really, really safe space and I loved it. As Matty says, the small moments are where the real, like there’s a sparkle to it.

For example, Seth, I knew him from a previous meetup where we bonded a bit, because we were the first to arrive, but at the Grand Meetup, then we were all super busy meeting, new people, talking to everyone. And on day two, I hadn’t met Seth yet, but we were walking down the hallway – each of us deep in a conversation with someone else – but we saw each other, we had a quick hug, smiled at each other and went our ways. There’s no function to that really but it’s great for the heart, for the soul.

CHENDA NGAK: If you didn’t know, we have a huge team of Automattic called Happiness. They are a direct connection to our customers and have a real pulse on how we’re doing. This team works 24 hours a day. So, they’re spread all around the world. I caught up with Nagesh Pai who is based in India. 

Nagesh is actually on rotation with another team right now, but that’s another story for another day. Nagesh, what’s it like to be at a Grand Meetup?

NAGESH PAI: In a single word, surreal you’re surrounded by some of the most talented people, I would say, I’ve ever seen. People whom I’ve always looked up to as a small person within the WordPress ecosystem. Maybe I began as a hobby blogger, and then as a freelancer, but always I’ve been wondering who are these wonderful people and great minds that contribute to it.

CHENDA NGAK: I was thinking about the Happiness team and how it’s so big and spread out globally. I would love it if you could talk about how important it is for you all to meet up.

NAGESH PAI: It’s very imperative to have very good connections amongst ourselves within the team so that we are following the same path we are following the same great vision of what we aspire to do as a company, to our users.

And at a personal level, it’s also important to develop best practices and learn the best things from each other. So while there is a standard set of things that we do as a routine on a day to day basis, we are scheduled to work six hours a day. It’s equally important to take a step back and see what are the individual flavors that we can add to these standard things that we do.

And that’s something which is very important to pick from our colleagues who are in our close circle. And that’s precisely where sort of a time out for those seven days, which we enjoy as a team meetup. It certainly helps a lot.

CHENDA NGAK: We mentioned that you’re on rotation now on a different team. That is something that is really unique to Automattic. I think it’s a really cool thing that we do. People can go on rotation to a different team for six months and just fully work there. Do you feel like, because you had been at a bunch of meetups before, it helped you transition to your rotation a lot easier?

NAGESH PAI: Certainly, I would like to add here that Automattic has a wonderful opportunity for each of its employees to try out different skills. And some of us have come with different backgrounds in the past, I’ve worked in marketing and corporate as well.

I also have a background as an engineer, not in computer science, but I like fixing things. During these meetups, I had an opportunity to chat with colleagues who are full-time into those roles and ask myself what next for me within this company to grow individually and also wherein I can contribute in a better way to the company.

And it’s not just about rotating to the coding role or the developer role that I’m trying right now. In the past, I had the opportunity of being a lead for my team for some time. I also did a rotation within Happiness to the WooCommerce division. 

So for all of this, I had to ask opinions from people who already done this.

All the answers to these questions I could get firsthand from people who’ve already done that. So this is precisely what I got from some of these meetups, across a dinner table or a nice pleasant drink.

CHENDA NGAK: I had already started interviewing Automatticians for this episode when I was tagged in a P2 post that felt almost serendipitous. Steve Blythe works on our Trust and Safety team on legal processes. He wrote a blog post talking about the importance of meetups at Automattic. It was exactly what I was building this episode around. Can you summarize what your post was about? And give me a little bit of insight into your inspiration on why you wrote it.

STEVE BLYTHE: I’ve been at Automattic almost nine years. I’ve been to a lot of meetups, a lot of different kinds of meetups over the years. Team meetups, Grand Meetups, you know, the Grand Meetup when it was 200 people versus 2,000 odd or whatever we’re at now. I think that especially over the pandemic because we haven’t been able to meet the kind of the dynamics in terms of our relationship with meetups has changed.

I wanted to share that internally because the company has grown so much over the past few years, even like throughout the pandemic. And there’s lots of people who’ve never been at a meetup, lots of people who’ve never met any other Automattician in person.

The summary of the post was to advocate for the importance of meetups, because there’s the danger, I guess, that, you know, having not had meetups for a long time, either people won’t want to go to them, won’t understand why they’re important, and will prefer to stay at home without really understanding what they’re all about. Or maybe I’ve just got used to not being around people. And It was to try and kind of, yeah, give that perspective I think.

CHENDA NGAK: You know, I was thinking about how people collaborate with each other in social settings at meetups. How do you think that translates to how we work together?

STEVE BLYTHE: Ooh, that’s a good question. I’d never actually made that connection before, or maybe not recently, but I think that, I think it’s the other way around, maybe like in the sense of we have these people that have got amazing strengths or particular skills and are often used to working very independently, cause they’re online might not be obtain their time zone or whatever it is.

And at Automattic we’ve always been kind of early spins started. We were always encouraged. Well, not just encouraged, I don’t wanna say forced, but we were pushed to discover things for ourselves and seek out answers rather than asking other people. So the autonomy part of working Automattic translates well into those situations where people can each bring something? I think that we want to make sure meetups have the opportunity for that, as opposed to just presentational style things, because in those cases, you’re given people that are used to working very independently and expecting them to sit there and listen, which, you know, you, you need to have a balance of that.

CHENDA NGAK: After talking to Steve, I wanted to hear from one of our leaders about why meetups are so important for the business. Nick Gernert is the head of WordPress VIP. They’re the enterprise team that powers huge websites like CNN and Salesforce. Do you have any favorite moments for meetups that you’ve attended over the years?

NICK GERNERT: I started on a Monday, I think it was September 23rd and September 27th was the start of Automattic’s 2013 Grand Meetup. I think there were almost 200 people at Automattic at that time. So it was, it was a great way to just jump right in and get to meet a lot of folks. I feel very fortunate that I got to do that and come into the company in that way. A lot of my fondest memories and like my formative memories around my time at Automattic have come, through meetups.

So, we have our Grand Meetup, which is like everyone at Automattic gets together in the same place. And then depending on what part of the business we’re in, we also get together within our teams. And so the team I was joining at that time was less than 15 people. And so we were having our team meetup.

This was my first team meetup and as part of the meetup we launched the homepage of Time.com. So it’s like, we’re all getting together for this first time. And you get to take this storied media property hundred plus years of just amazing journalism and being there through so many incredible historic moments. And here we are a team of 10 people or so sitting around the table and we’re launching the homepage of Time.com.

CHENDA NGAK: I wanted to get your perspective on meetups from a business standpoint. Why do you think they’re so important for companies like ours that are distributed?

NICK GERNERT: So inherently, you know, we’ve bought into this idea that like, we’re going to work from wherever we’re most comfortable for the majority of our time. And so there’s great flexibility with that. There’s great power that comes with being able to source talent and work from anywhere and things like this.

But then there’s always this fundamental belief that we, as human beings, are also social beings. The most high fidelity form of communication comes from being in the same physical space you could pick up on social cues. You can pick up on body language and just lots of things in the environment that influence that.

And so there’s this case for like, we still need to come together as human beings on a cadence and, and occupy this physical space and this high bandwidth sort of collaboration and communication. And I will admit, Chenda, it’s a bit anecdotal and I want to do more digging into this with like our data on our side, around just retention.

But as a bonding and just really getting folks, you know, brought together as a common and retention and retaining of these teams. A lot of our team has really bonded and it’s formed through these moments where we come together. Which may make you think like, well, yeah, if you were just together all the time, then you would also get that same benefit.

But there’s something really magical about this fact that you have this balance of flexibility and working and residing where you’re most effective. And then when you come together with the teams, it’s like this high energy focused, like you wanna maximize every moment of it cause you know, it’s a finite period of time.

And so you come together and it’s highly effective. So we also tend to think about meetups as what do we wanna accomplish through coming together? Which may just be like, look, our team’s very new and we need to just like help it help us form as an organization. So when you think about formations of teams and things like that, super important in doing things like that.

The other thought from the business perspective, as I thought about this, Chenda, is it just evolves over time. So when I think about, you know, the group that I’m part of was like, you know, less than 15 people, when I joined Automattic and a meetup meant like we could get all 15 of us around the table. Very easily. Like, this business is now 300 plus people in it. And so our concept of how do we leverage meetups evolves over time because the scale of the business matters and that context matters.

CHENDA NGAK: I was wondering if you had any tips for balancing your time at meetups, because it can be so overwhelming.

NICK GERNERT: One of the primary objectives in just coming together as a team in that space is really just bonding as a team. It’s great to have a shared sense of an outcome or an objective, but don’t overly index on those things. Like, don’t come into one of these settings and then put a very ambitious target on it, which then takes all of the focus away from coming together in a way that it’s, you don’t typically get to collaborate.

So, I think not over programming is a big thing. And then what’s been interesting as meetups have evolved, especially when we bring big groups together, like in the Grand Meetup is creating spaces both physically. And then just in the timelines that just allows folks to disconnect from the meetup for a little bit.

And then one thing that also just comes to mind for me, as I think about like how to learnings and programming is just really the importance of bringing folks together that may not collaborate day-to-day and building empathy for how we really are all contributing to common objectives, even though it may not always be obvious how, you know a sales team is working with product or customer support is working with sales or product or any of these other things.

And so how can we bring folks together and build empathy across the business.

CHENDA NGAK: I love that you brought up empathy because it reminds me of the importance of creating psychological safety. And I feel like these meetups really provide that. So, I was wondering if you could touch on that a little bit.

NICK GERNERT: Yeah. It’s so interesting. The concept of psychological safety is, like, once we’ve met each other in person, how it totally changes our perception of day to day interactions. Because when you think about a distributed work style and especially where we commit deeply to the idea of asynchronous collaboration. I may send you something, Chenda, and may have a question for you, but I don’t expect that you’re gonna respond in 60 seconds. You may respond to me the next day or later that day or whatever it is, but it’s not immediate. 

So, there’s a lot of text based communication and you lose a lot of signals that, you know, when you and I are just conversing. And so once you’ve been able to really meet someone in person and you understand how they communicate. Once you’ve put a face to the name and met in person done all this, you just have a totally different interpretation once you leave. You really do remind yourself. It’s like, hey, we’re all just people. We are all really trying to just do our best work for common goals. And I feel a lot safer now in the collaboration around that.

CHENDA NGAK: What sort of impact did you see when meetups paused during the pandemic? And what observations did you make?

NICK GERNERT: I think we lived both sides of this as an organization because up and through 2019, we just took for granted that we had this cadence of meetups that, you know, it was recommended once a year. We’re gonna get the whole business together. Once every nine to 12 months, you’re gonna get your particular team together. 

You’ll probably attend another cross-functional, cross-divisional, gathering and you had these moments to check in and reset and it really did help prevent things like burnout because it can be very isolating when you’re working in your particular space for extended periods of time.

And you can’t just easily reset humanity behind everything that we’re doing day to day. And even for us as a distributed company, as we went into 2020, meetups were essentially frozen no more, if we’re not gonna be meeting up. And we don’t know when we’re gonna meet up again.

So it created disparity around that and you could start to see how that was like weighing over the extended period of time. And at a certain point after a year goes by and no one’s meeting up. You can see this impact of like, gosh, if we could all get together and just bond again as individuals, and you could just see a collective exhale, because we’re all feeling the tension of just kind of like being in our respective space day after day after day and not having that moment to come together as people again. So, it really crystallized the importance of just, we need that time where we can come together as individuals and bond and share.

CHENDA NGAK: Ama Osei-Oppong is one of our HR Wangers based in Scotland. She connects with people every day for work. So she has great insights on the importance of strong connections. Ama can you tell me why it’s so important to feel that sense of belonging at a meetup?

AMA OSEI-OPPONG: I mean, I would say that the sense of belonging, and this is for me personally, other people may have their own views, but I just feel like you’re seeing and being around people that absolutely get the mission. They absolutely get what we’re trying to do at Automattic and, you know, it’s just that understanding and that collaboration, like for me, it’s a collaboration that I love the most. And sometimes, you know, it can be challenging. Not being all together to do that.

So it just allows you that additional option of getting together, working through, you know, projects or initiatives and actually just spending time with each other, getting to know each other as people, because sometimes you can come in and work and you maybe don’t always have that.

And there is something to be said, you know, when you’re working with people and you know more about them and they know more about you, it helps build that trust. And also helps you, you know, it helps you be comfortable and it helps you be creative as well.

CHENDA NGAK: We spoke about why meetups are great. Are there any downsides or challenges of meetups?

AMA OSEI-OPPONG: Downsides or challenges of meetups – I think one of the challenges are to actually keep focused. I think there’s the excitement of seeing your colleagues and seeing people, especially after COVID that you’ve maybe never met. And I think sometimes, you know, if there’s a session where there’s a business objective, sometimes it can kind of feel like it’s getting lost because there’s excitement of meeting everyone.

And I think the way to overcome that is when you’re really looking at the setup of your meetup and almost looking at the agenda, having adequate time for that social time – that getting to know each other and balance that off with your working sessions. So, that you’ve got that kind of delineation.

I’d also say possibly one of the downsides, and this is possibly an after effect of the meetup is that sometimes you all get together and there’s some conversations where like, you know what face to face conversation is probably better for that particular scenario. And sometimes it’s like, you have the energy of the meetup. You know, when everyone gets home, the day to day of the job kind of comes in and sometimes those ideas can get lost. 

And actually it’s almost that way of really – there needs to be a commitment that whatever is agreed and discussed at the meetup there’ll be like an absolute commitment to see those along when everyone gets back home.

CHENDA NGAK: Meetups have been part of Automatic’s culture since the start. Donncha O Caoimh has been at the company for 17 years. He’s experienced the good and bad parts of meetups.

DONNCHA Ó CAOIMH: I think practically the only time we get to talk about personal issues and just talk about life is at the meetups and at our team meetups.So that really does help to help us bond. And even besides that, it helps, helps us brainstorm issues.

It’s a great way of just getting to know my colleagues, because we can walk along the streets to a cafe or a restaurant where we’re going for dinner and we’ll talk about personal things that you’re not gonna talk about during a work Zoom call because a Zoom call is just an hour where you have to concentrate on what you’re doing, and you should talk about business issues or you’re talking about programming problems.

Whereas when you’re in ordinary life, you’re walking along with another person and you get to talk about ordinary things. It helps to build that relationship with the people I go with.

CHENDA NGAK: But there are challenges for folks who are more introverted as the company has grown. The dynamic of meetups has changed. Trying to connect with a hundred people is different than meeting 2,000.

DONNCHA Ó CAOIMH: It can be stressful because you’re you go from sitting at a desk for, 48, 50 weeks of the year, maybe communicating with a single group of people that you know, pretty well and suddenly you’re thrust into this confusion of faces that can be tough.

CHENDA NGAK: The next person I spoke to makes tough decisions on a daily basis.

David Watkis is Automattic’s Director of Trust and Safety. His team oversees policy and content moderation for WordPress.com and Tumblr. He spends a lot of brain power thinking about complex situations. If anyone could talk about building trust and how meetups help with that surely it has to be him.

DAVID WATKIS: Meetups tend to be unique depending on what the primary goal is of that meetup, depending on who’s attending, and even just where in the world we’re located. I think there are some through lines, however. Some similarities that I would say are our takeaways from every meetup. For me, the biggest thing is just the ability to make leaps forward in the work, whether that’s discussions that we’re having, particular projects we’re working on and deep trust and safety policy decisions that need to be wrapped up. These things can happen online and certainly they do.

But when you have sort of six months of like asynchronous work, it can become a little more difficult to land the plane. When you have everybody in the same room, it’s really nice to sort of tie up those loose ends and. Move to the next milestone or indeed move to completion. They’re also really grounding experiences.

It’s easy to lose the thread a little bit when you’re working strictly remotely, or certainly primarily in text. So, when you’re on the ground and in the same place as somebody, it’s just a good reminder of how great your colleagues are, why we’re all at Automattic and, and now we’re all on the same team and sort of pulling in the same direction.

CHENDA NGAK: So when I was thinking about trust and safety, I thought this is a role that requires clear thinking, a calm mind and trust within your own team. I would love it if you could talk to me about the importance of connecting to build that trust within your team.

DAVID WATKIS: Yeah. So building trust within teams, whether that’s trust and safety, whether that’s any team in Automattic is so important. And meetups, in my mind anyway, are one of the primary ways in which we can do that. We’re certainly making those connections online in trust and safety, certainly.

We assume positive intent with one another. When we’re discussing policies, when we’re making decisions, we have frameworks for giving one another, the confidence checks we need when we are not feeling so confident or so sure about a decision about a course of action, but all of those things are, you know, one step above one step further when we’re together at a meetup.

It’s just different when you’re breathing the same air as somebody and sitting down in the same room with them. We can hear the intonation in each other’s voices. We can see the mannerisms, the other cues as we’re, as we’re talking and, and listening. There’s also typically a social component at these meetups, whether that’s just hanging out after dinner to talk shop to get to know one another or even something more structured, like going on a food tour or attending an art class together, you know, what, whatever it might be.

It really creates these team bonding moments that just aren’t possible when we’re remote or working strictly online. I would say it’s also a bit easier to be vulnerable and to be ourselves when we’re all together in the same room. So, if there’s somebody, a colleague, a teammate who’s perhaps suffering from imposter syndrome or who’s been struggling to complete a task, it’s a lot easier to raise your hand and ask for that support when you’re with your colleagues in the same room.

CHENDA NGAK: Do you find that there are unrelated skills that you pick up while you’re there meeting with other Automatticians?

DAVID WATKIS: You know, my line of work is such that the applicable skills tend to be quite specific. Having said that, a conversation that stays with me probably daily, is advice that I receive from another Automattician and another area of the company at a Grand Meetup, which was, “Never waste a crisis.”

Which took me some time to digest and understand exactly what that means or how to apply it. But I would argue true regardless of field, but certainly in trust and safety, when things go sideways and they inevitably do go sideways, it’s a great opportunity to pause, to reflect, and course correct in a way that hopefully allows you to sidestep a similar crisis or that same crisis, in the future.

In the trust and safety field, we tend to be problem solvers when the issue presents itself. It’s, “How do we get to the solution as soon as possible?” But acknowledging that crisis, not wasting that opportunity to have a teaching moment, have a learning experience. So that we’re not rushing into the same issue, the same pitfalls in the future is incredibly valuable. 

And that is a piece of advice that I got at a meetup, in a random conversation with someone outside of the trust and safety field. And so a great example of how those minor connections and those minor sparks can blossom into things that indeed become guiding lights as you navigate this career and, and these different areas of focus that we all have.

CHENDA NGAK: One of the absolute unsung heroes of a grand meetup are the folks that orchestrate the whole thing. Megan Marcel has been with Automattic for six years, leading internal events. If you need tips on how to throw a week-long gathering for a thousand people, hit her up. Okay. So tell me, what does it take to pull off an event of that size?

MEGAN MARCEL: Yeah, so I think one of the first key things that we try to do is get together the key stakeholders and really outline, “What are the objectives and goals for the meetup?” What do they wanna get out of it? We also, a lot of times, will survey folks at Automattic to hear.

In addition to what leadership is hoping to get out of this, what do the employees wanna get out of this? And I think really helping to meld that all together is super important. So, after getting that kind of buy-in from key stakeholders, what I will usually do is prepare a bit of a draft like block agenda, if you will.

I think that social is just as important as the business, while we’re on site, just because of why we’re meeting and being remote. So making sure that there’s a really good balance between the two. Also people are used to working from home every day, as I mentioned. And so it can be tiring. So, making sure to put in a good balance of breaks, just so this way, when people are showing up, they are really present.

 So once we kind of go through that and have a general agenda in place, we’ll start locking in speakers, workshops, breakouts.Some of those being led internally, some of them maybe will bring in external speakers and then finding little elements that we can add in throughout to just bring the culture of Automattic.

CHENDA NGAK: How do you go about finding a venue for our meetups?

MEGAN MARCEL: We definitely wanna be mindful that we don’t have the bulk of people traveling 16 plus hours and some traveling only one hour. It’s not always possible that everyone has a short journey, but we do try our best to look at a central spot. Given the budget, we also will just try to keep in mind, staying away from any high season.

Being flexible on location. We have really strong relationships with some hotels where we’ll use our global salesperson to help us, you know, really just hone in, on places that feel Automattic. And what I mean by that is just really the whole vibe of the space.

Say it’s a meetup for 250 people. We don’t want to be in a hotel that’s for 3,000 people. We really want to feel like it’s our home base for the week and not get lost in it. We try to keep that in mind. We also try to look at locations where it may be a bit easier for people with visa requirements.

Being a global company, we do have people from all around the world attending. And so we try to get ahead of that when we can, we try to help build travel history through other events and meetups during the year. And that’s one of the things that we look at. So, while it might not be a perfect science, we try to look at all of these different things.

And then, you know, how much space do we need? We are a big team. We have breakouts. And so having a meeting space, that’s a big enough size. I would say we always get creative there. Sometimes we might use a suite in the hotel if there’s not enough meeting rooms or maybe there’s a restaurant that we can grab a private room in and have that for during the week, if we don’t have enough meeting rooms necessarily.

So, just trying to get creative where we can keep in mind costs, also you know, when we look at the dates. Availability becomes a big thing, especially a group our size, but we also wanna make sure that we avoid any holidays, times where it would be really hard for people to be away from home. And so incorporating that into our search.

CHENDA NGAK: I believe we have more than 2000 Automatticians in almost a hundred countries. Now, how do you approach logistics with everyone being so spread out?

MEGAN MARCEL: We have channels set up where people can ask questions on different routes that they might be considering taking. And so just a lot of support on that, wherever we can help provide it. I think it does a lot for people to feel comfortable attending. 

Also just taking into account cultural norms where people might be and can we incorporate any of that into the meetup? Is that through food? Is it having a prayer room set up? Like what can we do in those instances so that when people are away from home for such an extended amount of time, they feel comfortable, they have what they’re used to. Maybe not in everything, but we definitely try to take it into consideration.

CHENDA NGAK: Now that I’ve heard all the great stories from past meetups and why they’re so important, I thought it would be great to hear about how to optimize our time at meetups. So I spoke to someone that has so much wisdom to share.

JOSEPHA HADEN CHOMPHOSY: My name is Josepha Haden Chomphosy. I am in Southern California. And what I do here at Automattic is I run our division that focuses on the open source practice, specifically for WordPress.

CHENDA NGAK: What’s it like for you to attend a meetup as a team lead?

JOSEPHA HADEN CHOMPHOSY: For team leads, if you’re leading a group of people, when you go to a meetup, it’s really important that you kind of realize that your event starts the moment that your team knows about it. 

It’s not always the case that the team lead is the organizer. Sometimes the team kind of organizes your event together. I think also as attendees, there’s a lot that you have to do ahead of time to make sure that you are using your time, the best and you’re looking after your own energy. Like in order to make events really functional as a way to move through problems that you find when you’re working in a distributed way, it just, you have to bring a lot of intention to it.

CHENDA NGAK: Can you share any tips on how to make the most of our time together?

JOSEPHA HADEN CHOMPHOSY: One of the things about in person events, in a distributed sort of ecosystem in a distributed organization, is that you really have to put a lot of effort into making sure that it is the most effective, the most efficient that it can be. Cause it happens so rarely. I like to remind any of my leaders and certainly anyone on my teams, that 90% of your work, if you are doing any of the leading, needs to happen before anyone actually gets there.

Then, also, if you are going to an event as an attendee, you really do have a bit of research you have to do ahead of time, just to make sure that like, everything that could be done ahead of time is already done so that you don’t necessarily have to figure that out once you get there. And so some of the things that anyone can do to make sure that their event is the most effective, the most efficient use of their time and their team member’s time is one, always keep in mind the level of ask that you’re bringing to that event. You have so much you have to do ahead of time. 

And so if you are a team lead, if you’re a leader, one of the things you have to know for sure is the reason behind why you’re gathering. You have to know why you believe it is that you are better together. So, if you’re bringing folks, in order to learn or to plan something or, or simply just to get connected, It’s good to know what that is. And then you have to ask yourself some important secondary questions, where are my weakest relationships, or where have I seen the weakest relationships within my teams?

What questions do we not ask ourselves often enough? Or how can we get to a shared vision and make sure that what we are working on is what everyone should be working on? So, those are the sorts of questions you have to ask yourself.

CHENDA NGAK: Do you have any personal life hacks, any routines that you do before you attend a meetup?

JOSEPHA HADEN CHOMPHOSY: Yes. So, any time that you’re attending a meetup, but certainly right now, one of the most important things that you will not believe before you get there is that it is exhausting. Like you’re working in a different way. Physically, you’re working in a different way. Mentally, you’re working in a different way. Emotionally, your brain is working in a different way. 

Like everything about working with people, especially over the course of a week or two or three days is so different from working with people when it’s just text based. One of the things that you have to remember as you’re headed into these events is that you’re going to need to pace yourself. You need to think about how you need to be able to show up over the course of the event. And so you have to look and make sure that you are accounting for consistency of showing up over time, as opposed to the average of showing up over time.

And so the thing that I do before every event is sit down and look at who is going to be there and who I would like to make sure I connect with for whatever reason and then message them ahead of time.

CHENDA NGAK: We really consider meetups to be our secret sauce at Automattic. Why do you think that is?

JOSEPHA HADEN CHOMPHOSY: I think it’s generally true that one Automattic believes that many eyes makes all bugs shallow. Right? We believe that we can go further together because we believe we are better together. 

But also, I believe that Automatticians, like, people who work at Automattic are inherently kind of social animals. And we really commit to the idea that all of our combined experience is better than any individual person’s experience. I think that’s true for folks who work at Automattic, we tend to attract that sort of attitude.

MATT MULLENWEG: Hey everybody, Matt Mullenweg here again. It was great to hear my colleagues share their stories and speak from the heart. As you heard from Megan Marcel, it takes a lot of work to organize a company-wide meetup. People fly in from all over the world, spend a week away from their families.

So, I appreciate why they’re meaningful from diverse perspectives across Automattic.

Like many companies across the world, Automattic is very closely watching its budgets right now and how much we’re spending and trying to reign things in a macroeconomic instability. However, especially post pandemic, we decided to invest in meetups and getting colleagues to see each other in person.

It’s kind of funny that after, you know, 17 years of telling everyone to be distributed and remote, that now I’m beating the drum of people getting together in person. And of course, we all want to be connected to our colleagues, to our work, to our communities, to the fruits of our labor. And meetups are our fantastic way to do that.

Thanks to everyone who took the time to share their stories and the Chenda for going on this journey of discovery. Hope this episode inspires other leaders to invest in bringing people together. Thank you so much for listening. See you next time.