Episode 15: Inside the Grand Meetup

Okay, go.

The song that's in my head right now is, "Good morning, good morning." My name is Josepha Hayden-Champussy. I shouldn't say it like a question. That is my name. My name is Josepha.

Great to see you. Thank you for stopping by the Automattic podcast booth. Josepha, what do you do at Automattic?

Great question. A little bit of everything. So I actually am the lead of the .Organization division, which is the division that supports and helps to guide a lot of our open source work with the WordPress project itself.

Who are you? Tell me your name.

Oh, my name is Aaron Douglas. I am a mobile wrangler for Automattic. My official job title is actually Chief Tater Tot Officer. I neglected to change that and it's just sort of stuck. So I work on the WooCommerce mobile app as my primary thing, but I kind of am everywhere around Automattic. I try to help out where I can.

Okay, here we are in the hallway again. What's your name and what do you do at Autimattic?

Hi, I'm Brandon Kraft. I'm a code wrangler working with our Jetpack plugin.

What is your name?

Sherry Bigelow.

And what do you do at Autimattic?

I am an excellence wrangler.

Well, my name is Rocío Valdivia. I'm from Spain and I'm a community wrangler in Autimattic.

I'm a chaser and I'm with the legal team.

So my name is Will Brubaker. I am the chief mechanical officer.

So hello. I'm Erin Casali, often referred as Folletto, and I currently work as the design lead of Jetpack.

How long?

Yeah, it's been a while now. It's 6 years.

Where are we now? Here.

So we are, I think, in Orlando because we are inside a hotel and been a while, so I'm not entirely sure where we are. Your hotels look all the same. But no, we're in Orlando. And like, what it is, I also lost count of time. I think we are day 3 or 4 It really is a blur, isn't it? It is.

Thank you for being here.

Howdy, howdy. I'm Matt Mullenweg, the CEO of Automattic and the host of The Distributed Podcast. Those voices you just heard, those were automaticians, folks who work for Automattic. And today we're going to be hearing from them about this year's Grand Meetup. And more broadly, what distributed work means to them. Back in September, Automattic held its annual Grand Meetup, which is the one time during the entire year that pretty much everyone in Automattic gets together in one place. The other 51 weeks of the year, we all work from different places all over the world, over 70 countries now. So this is a chance for some of us to check and meet face-to-face for the first time and for everyone to catch up with old friends, discuss our work and align around goals, and hear great talks from folks like Stephen Wolfram. Who was a guest on this podcast a few weeks back. We set up a recording booth at the meetup and talked to a bunch of folks from around the company to hear about their experiences with distributed work. My colleagues Mark Armstrong and Ben Huberman were on the ground asking questions throughout the meetup. Mark and Ben are from Automattic's editorial team, and they've also been helping out a ton with this podcast. We'll kick things off with some automaticians talking about why meetups matter for distributed teams, then get to an interview with Megan Marshall, our Director of Global Events and Sponsorships, about what it takes to pull off this huge event with so many people. I think we had like 900 at this time. Then we'll hear some remote work tips and finish with some stories about why these folks have chosen the distributed lifestyle. Okay, let's do it. Take it away, Mark.

Okay, thank you, Matt. Now that you've met some of our colleagues from Automattic, let's go deeper and learn a little bit more about their experience at the Grand Meetup. If I can set the scene a little bit, Ben and I stationed ourselves at different tables outside in the hallways of this conference room in Orlando, just a few miles from Walt Disney World. And so we just flagged down people as we saw them, or people would see us with a microphone and say, "Hey, what's that? Can I get interviewed?" I have to say, it was super fun to have an excuse to pull people aside and interview them and ask them about their experience at the Grand Meetup. It can be such a nerve-wracking experience to be surrounded by all these people you work with. So it's just fun to take a step back and look at the scene and ask some questions of each other on what it's all about and why we're even there in the first place. Now we're here at the Grand Meetup in Orlando, Florida. Now what is the Grand Meetup?

The Grand Meetup is basically like a company all-hands. I think that's how corporate places we call it, where we get everybody from the company who's able and willing together in one place to do some additional training, additional team building, and a lot of, like, a lot of this thing that has to happen when you work in a distributed company. So, when you work in a distributed company, every time that you interact with your colleagues via text, or however you are away from them, you are taking out of your social bank account. With them. And so when you get people together, that's when you have the opportunity to, like, see each other face-to-face, remind everybody that, that you're all human beings, and fill that social capital back up. Because, because it's so hard to communicate via text. And so that's one of the main, I think, benefits of bringing everybody together this way. Of course, we have a lot of trainings and a lot of opportunities to have high-bandwidth conversations, but I think that's one of the main benefits, and it's almost a side-effect benefit. I don't think anyone thinks actively about that when they bring everybody together for this.

Now, when did you join Automattic?

November 1st, 2018. So I give a flash talk this year. It's my first GM.

Fantastic. So what— how has it been so far?

Of the GM? I love it. I love it. I'm meeting all these people who I've been working with all this time, and it's so awesome.

Awesome.

It's like the best in the world.

It's a very energizing experience. My job is very demanding, and my life is very demanding, and everything around us is very demanding. I start to get de-energized in about July or August, and it's also like things are physically— it's hot outside, things are more difficult in this time of year, at least for me. But then I get here and I, I get around people and I, you know, I, I ask questions that are that are on my mind, and I'm not— you know what, I'm passionate about, and I, I want a real answer here. And you know what, I get a real answer, and I get an answer that inspires me and that makes me want to go home and work harder. You know what, I'm empowered now to fix the things that have exhausted me, um, and we're going to start over and we're going to move towards next year's goals. And I'm very clear what those are, and that's what this does for me, is it, it's a reset. It energizes.

So right now we are in Orlando for the annual Grand Meetup. What does the Grand Meetup mean to you?

Wow.

The Grand Meetup means a lot of things to me. I love the energy. I come back home with all my batteries charged for the rest of the year. I'm very aligned with the values of this company, and I'm very aligned with the kind of people that I find here. In general, I think nobody's normal, right? And everybody is different in so many different ways. And in this company, you can be however you want to be and nice to each other. And something that I will highlight as well is that everybody help each other. I love that. And what I value the most about the GM is the connections that I create in person. Then I can, use them, you know? It's like I take advantage of all the connections I create in person during the GM the rest of the year. I learn more what people do. For example, I sit down and I meet someone during lunch and, hey, this person just tells me that, you know, works on marketing or that is working on this and that. And then we have a conversation and we realize that we have so many things in common. And then, for example, a marketing team can help maybe with WordCamps and then we start start planning, oh, we should do this and we should do that. And I love it because normally those kind of things doesn't happen during the year because you are so focused on your daily basis job that you don't have the time to, or you cannot find a lot of times the time to just hang out in different teams channels. I don't normally do it because you are so busy, right?

What was your first Grand Meetup like?

My first Grand Meetup was terrifying. So I'm a wild extrovert, especially compared to a distributed technology company standard-issue employee, right? Wild extrovert.

What are you talking about?

I've never heard of such a thing. But yeah, I was told by my team lead at the time that I didn't need to prepare for anything because I was so extroverted. And so I arrived, and I had no idea what to expect or who was there. Like, I joined on a tiny team, like 7 people, maybe 6 even. And so I joined, and I knew them, and that was it. I didn't know that there was this whole other company going on. I didn't know that we had, like, classes we had to attend. I just kind of showed up to stuff randomly on the day that they were happening. And it was really stressful, even for me. I remember thinking at the end of it, like, I'm not sure that I'm an excellent fit here. I wasn't prepared. Everybody knows that. Everyone, I don't know anyone, I have nothing in common because of course I hadn't spent any time trying to figure out where I was headed. And so yeah, it was really stressful, but I—

It's a sensory overload, isn't it?

Yeah, yeah, it's like the first time you go to CES, in case anyone does, like you can make it about 2 and a half days before you're like, this is terrible and I'm gonna hide in my room until everyone is gone, and then I'm gonna get on the first very slow transportation out of here And that's it.

But it's like CES, but they're everyone you work with and a bunch of people who you have already chatted with.

Yes.

But you have never met them in person.

Exactly, exactly. And you're not sure whether you like inadvertently offended them. And sometimes you completely forgot to respond to them because you hadn't figured out how to use all the communication channels yet. And so like, I asked you something 2 months ago. It probably shouldn't have been time sensitive, but now I'm mad and it is, you know? So you run into all these surprises. Because you hadn't figured out how to communicate, you hadn't figured out how to work with all of the information that comes in, 'cause there's so much information all the time, and you have to be proactive about finding it, which is good in a way and also really difficult in ways as well.

So we're in a big hotel complex in Orlando, Florida right now.

Yeah.

So we've got a bunch of employees in front of us.

Mm-hmm.

I mean, how does this compare to your first Grand Meetup?

It was so much more casual. 'Cause if you think about the difference between 300 employees to almost 1,000 employees, and the types of employees and the roles that they have that we've taken on since then, it was so much more casual, it was almost familial before. And I don't know if it's mostly a matter of the way that my work has changed, but I remember that I was in full discovery mode the whole event, and just like trying to figure out who did what and why and where all the work came from and what we were doing and why we did it. And now it feels like— and I don't know if it's accurate or not— but it feels like for the most part, everybody already knows where they're supposed to be, what they're supposed to be doing, how the work is supposed to go. Like, we show up and everybody already has this excellent plan and a goal for what to do for the week, even if that goal is finish my support rotation, you know? And I think that's a really nice thing to have a really easy collegial sense, which before was kind of like a, "Hey," casually showing up and figuring out what we do now when we have arrived, you know? It's a different thing, but I think a really pleasant thing.

Now, there's another element to Grand Meetups that continues to this day, although it's evolved a bit. Your first Grand Meetup, correct me if I'm wrong, you did not know that you were going to have to present a flash talk?

Yeah.

I didn't quite know. I didn't quite know. Like, I had never seen a flash talk. I didn't even do any research. I arrived and someone had told me, like, "This is a thing that has to happen, but it's really easy, again, because you're an extrovert, and so, you know, you show up and you talk for 4 minutes, it'll be easy." Now, I love public speaking, and I have done a lot of it, and 4-minute presentations for me are way harder than 45 minutes, because you have to, like, choose and plan what you're gonna say every second of all of that. You don't have any room for extemporaneous chatter. And so, I showed up and they were like, "We never received your slides." And I was like, "What slides? Why do I need slides? What is it? What is a flash talk? It's short. I thought I just had to get up and like say my name." And so, I had to suddenly pull together slides and it was the most boring, bland title for a talk I could have ever managed. It was like, "Learn to be a better mentor," which is super on brand for me. And also, especially seeing what I do now. Super on brand for the future of my work here. But I didn't know that at the time. No one else knew it at the time. I was just like someone here to manage meetups. Man, I felt so stupid because everyone else was like, "Making paella the best. Why Spaniards hate your stupid ham." And mine was like, "Be a better mentor." I was so serious. I showed up and I was serious. It was mildly embarrassing, but I survived.

I have to say, I think I remember watching your flash talk and saying, "Yes, Josepha's here!" Like, I was— I really enjoyed it. I remember enjoying it.

Good, good.

Kudos to you.

Thank you.

But it is a funny thing because you come in and you think the Flash Talks are going to be half about work or, you know, maybe some lighthearted stuff, but very rarely are they about your day-to-day work. We have such a talented group of people at this company, and that's what you like. I feel like I learned so much from these Flash Talks. It's just that people have such diverse interests and hobbies and passions.

It brings back that human element and humanizing people again and reminding people that like, we're more than just a happiness engineer or someone on editorial. Like, there's more to who we are than just that one thing. And I think that's really special and really important and something you don't get in corporate settings that are this size.

Mm-hmm. What are some other pro tips for attending a Grand Meetup?

I mean, I think the thing that is most important is to consider what your boundaries are before you come. Like, it's so easy for introverts and extroverts to get swept up in the excitement of it and like, are you willing to stay up till 2 in the morning in the party suite because that's where the people that you had dinner with ended up? Because if you don't, you don't prepare for it. Like, if you normally go to bed at 10 o'clock at night and wake up at 6 AM and have a really clear routine, and then you get so far off your routine because you're so excited and you want to connect with people and learn more about them, you can really forget to prepare yourself for that and just wear yourself out long before the event is over. Because especially now, like this year, we have these big team days for the first day and a half. And then a bunch of individual trainings all the way through, and ways that people can learn and do high-level planning and teamwork throughout the week. And like, you want to be remotely fresh all the way through that. And if you just don't remember that you plan to be an extrovert this week, and so your introverted self forgot to, you know, have lunch by yourself in your room, you'll feel really overwhelmed by the end of it. And so just planning for that, Knowing what you're wanting to do and how it's going to change your routine and being mindful of that for yourself. It's the biggest thing I think anyone can do before they come.

What's been your favorite part of the Grand Meetup so far?

That's a hard question. There's so many great parts of the Grand Meetup. In some sense, we have some amazing keynote speakers and hearing these folks that we would never meet in person otherwise and having some really great insight there. But frankly, really it's just this time here, like right now in the hallway between sessions, being grabbed by you, Mark, just to talk for a few minutes. I really like that ability to meet with different people like that, that we wouldn't normally ping each other on Slack because we don't really have an operational reason to, you know, in the next few weeks. But we know each other and we see each other and we kind of rekindle that relationship even though we don't work together day to day. And if we never had the Grand Meetup, we wouldn't be able to keep that going. And so I think the best part is just seeing people that I know from other parts of the company, and even if it's just a quick hello or a handshake or a cup of coffee or 5 minutes on a podcast, I really think that's the most valuable part of the grand meetup.

Now, what are you doing this year? Are you doing a project?

Well, the past few years I helped organize the classes. This year I just taught a couple of classes, well, more workshop. I kind of prefer the workshop format. So, and this year I was doing, I was helping out with one on flowstorming. Which is a workshop technique to synchronize and discuss processes. And with Temi Lister, we worked on one instead on fast design. So how to generate ideas fast, quickly, how to push ourselves to create wild ones that then can become useful to projects.

What else happens at a Grand Meetup?

A lot of things, like, especially this year is probably one of the most varied ones. So you have a combination of assigned tables, which is something that at the beginning you're like, why are you assigning a table to me? But then it's, if you feel like relaxed because you're like, yep, I know I need to go to that table and I know it's going to be all new people. And so you chat, you know new people, and then there are keynotes, so external speakers, and then there are projects, and then there are a lot of like occasions to catch up with people and coordinate things. And one of the most beautiful things is how some of the, in the free time between activities, how naturally some discussion pop up. So for example, today I'm just out of a discussion that was organized 1 hour earlier. And because some teams felt the need to discuss about some critical topics, some problems they found, and they pulled in the right people. And in an hour, we were able to identify some problems, identify some steps forward, It's still a challenge, but now everyone is synchronized. And it happened just because someone was like, yeah, let's pull the right people in the room together.

When you have something like that happen, do you sometimes ask yourself, why do we not get together more often?

Frankly, I think there is a balance there. There is, of course, times when you're like, oh, I really need to pull people together. But remotely, you still can. Sometimes it's just a matter of, you know, spinning up a remote chat. In a way, sometimes it's also faster remotely because everyone is just a ping away. You know, you send a private message, and that's very, very simple in a way. And for me, that's one of the powerfuls that is a bit understated when we talk about remote work, because in practice, very few discussions actually require people to be there in person. What you need is people to synchronize, and there are many ways to synchronize. And so in this case, I think this could have happened also digitally, but it's just effective because we're here.

I mean, how does it feel to you seeing the evolution of the company and the evolution of the Grand Meetup for you to be in this giant hallway and surrounded by 1,000 of your closest colleagues?

It's really funny because I came into this meetup like, "Oh, Grand Meetups are not the same. It won't be the same feeling anymore. This one, it's too big now. It's like I don't know anyone anymore." And I thought like, "Oh, maybe it won't be as good." But when I got here, I found that I can't move through the hall without stopping like 20 times, so it takes me really long to move from one place to the other because I recognize someone, I see someone I worked with, I see someone I've only met online ever before, and I want to say, Hi to everyone. And so yet again, I'm here saying like, I love everyone, but I haven't met— I don't think I could possibly meet them all, actually. There is some like really nice balance for me in the sense that I can have some like great deep conversations and see my teammates. So there was time set up for teams in the beginning, which I greatly valued. And that whole like, this is massive feeling like, oh my gosh, look at this. Room that we filled with people who are my people. They're just like me. And that's like one of the things that I thought when I first— like the very first like WordCamp San Francisco that I went to, I was like, these people are all just like me. These are my people. Like, these are my people. So I feel like a strong connection and a special place in my heart for like everyone before I even meet them, probably. Pretty much, because I know that if you work here, you're probably pretty great.

Had you met any Automatic employee in person before the grand meetup?

Uh, in person before the meetup? Yeah, a few.

So just to clarify, before you joined the company, you had— in the interview process, none of that was in person, right?

No, none of it was in person. But I'll tell you the reason that I even applied. So I saw this job. Right, posted the corporate paralegal position posted. And I was like, who is this? What's this company? And so I went and I did my homework. And when I got to the HR page and there was the link to the diversity inclusion videos, I went there and I started watching those videos. And tears just started shooting out of my face. And I was like, These are my people. Every single one of them spoke to my heart. In 2016, I got laid off from a consulting job, and I had to take an in-house job that required me to be in an office in San Francisco. And I will just tell you that I feel closer to the automaticians than I felt to those people sitting next to me in that office, because in an office Sometimes you form cliques, right? And so I'm 60, you can see my hair, I'm, you know, and these were all very young people and they all were, you know, they partied a lot, they were still in that age. I've been through that age, but I'm not there anymore. And so it was very hard for me to integrate myself in that community. But, you know, at Automattic we have interests, interest groups, I guess you would call it. You know, we have Slack channels for every level of interest, and I have never felt more included in my life. I have people coming up to me at the gym, "I know you from this channel!" "Oh yeah, I love what you said here!" "Are you gonna do this?" and "Let's do this!" And it's like coming to family. You know, it's like a family reunion.

Tell me about your flash talk.

Mm, okay.

What is a flash talk?

So a flash talk, every first year— now, I hear I lucked out because it used to be every single person every single year had to do a flash talk, until what year?

I would say that would have been like 2016 or 2017.

See, I just lucked out. So now it's every person at their first GM has to give a 4 minutes about me, right? So whatever, not necessarily about you, but whatever you want to talk about, you've got maximum 4 minutes to do it. And I really freaked out at the beginning, which is funny because I do speaking engagements all the time. I used to run an education program. I did, you know, talking all the time. Time. But this whole 4 minutes about me was just like, ugh. But I did it. Well, I haven't done it yet, but I prepared my flash talk. It's about aging and adventure. It's called "When Does the Adventure End?

30, 40, 50, 60?" Spoilers: can you tell me when the adventure ends?

Never.

It never ends. It absolutely never ends. It just depends on how you approach it.

Right?

And now, how does this compare to your very first meetup? When did you join Automattic?

It was barely 2 months before the grand meetup that was in San Francisco and also Santa Cruz, California.

How many employees at the company at that time?

Oh gosh, I think, I think I was like number 220 at that point. It felt like a large company to me at that point, and having not come from the WordPress community— I've used WordPress, but I have an iOS developer background, some Android as well— my sphere did not include the community around WordPress. So I felt kind of a bit out of sorts when I first came to the Grand Meetup because I felt like I didn't belong. But it was like maybe an hour in, after sitting on the couch at the old Automattic headquarters, that I immediately knew that I was at the right place connecting with the people that were there and just felt very welcomed and included. And I was already in on the jokes on day one, so it was great.

That's fantastic. So how does the vibe compare? You know, 220 employees to here, here we are with going on over 1,000 employees.

Well, I mean, realistically, the vibe hasn't changed all that much in my mind because there aren't that many times that you're all together in the same room. So I will say that if we're doing a major town hall or we're doing a keynote and you happen to turn around, then yes, it's very obvious that we're a lot larger. I'm one of those people that tends to sit in the front row, so my perspective hasn't changed all that much. But when it comes to the hallway conversations and we tend to do training or classes, people hold classes for other automaticians to teach their own things that they've learned. And those are still relatively the same size, and those conversations haven't really changed their format at all. So yes, we've grown in scale, but really the heart of what the annual Grand Meetup is, is still the same, at least in my mind.

Why, if you're a distributed company, why would you have a Grand Meetup? Why would you do this every year?

Financially, it's, it's a hard hit on Automatic's books. It's just because you're flying everybody into the same space, you're giving them a place to sleep, feeding them fairly well, actually. But the reality is, it's hard to quantify what the Grand Meetup gives us in material things. Swag, I guess, we get, so that's cool as an automatician, but the reality is I'm developing relationships with people across Automattic that I may not have a chance to work with on a daily basis. I have not crossed paths with you actually all that much except for a few editorial PR-related things, but we've had a ton of conversations at the jams over the years. And what I would like to call— well, we use Slack, so I'll just say Slack— the Slack effect is that when I've met someone in person, and I've heard their voice and I've seen their eyes and their face, if I have further conversations with them after a Grand Meetup, my brain has a hard time discerning whether or not the conversation happened in person or like in a Slack or offline asynchronous manner.

So you're able to project that personality and conversation onto all sort of communication thereafter.

Yep. Like if I'm reading a message from you, Your personality sort of bleeds through into how I'm interpreting things to be written. And if I haven't met someone yet, I have like a general Automatition voice, you know, assume positive intent and all that, but I think it really helps make me not feel like I'm alone at my house when I have all the Automatition's voices when I'm interacting with people through electronic means. To me, the Grand Meetup is essential for me to feel successful.

What tips would you give in terms of how to navigate the Grand Meetup?

Listen to yourself. If you're in a state where you are overwhelmed, or if there's just so much input, too many voices, too many smells, too many places to go, you feel like you're being left out of things, like, it's okay to just Find a quiet place, sit for a bit, process your thoughts, and then continue on with the day. Like, if you need to go hide in your room for a little while, it's perfectly acceptable. It's a lot to take in. You are quite literally, from waking up to going to bed, always subject to things happening. It could be meals, it could be keynotes, conversations in the hallway. We all work from home. We have a lot of control over our day, and here you sort of have to give up a little bit of that control. That can be overwhelming. Self-care is really a big thing. The other tip that I would give any new automatician is just to say hello. It's amazing what I've been able to do by meeting people here at the Grand Meetup that I don't normally work with on a daily basis, and how that's helped me even years later when I do need to get something done for my job that happens to work with a team that I haven't been able to work with before. And I can look at someone on the team like, "I had that conversation with them at lunch that one year." And suddenly when there's a conversation about work, there's like a level of respect or a level of known truth coming from you to that person because they've had a previous conversation. You're not just some unknown. It's this very subtle difference, but just knowing who you're talking to and having that conversation that passes really helps me in a lot of cases.

What is your name?

Sherry Bigelow.

And what do you do at Automattic?

I am an excellence wrangler, so we do automated testing, manual testing, and keeping track of all the bugs for— I specifically work with the mobile Division right now.

And how long have you been with Automattic?

Going on 11 years.

That's pretty close to the founding of the company, Sharon.

It's quite close. Closer than it is far.

Yes.

A lot, actually.

Explain to me what your first Grand Meetup was like. Did you have a Grand Meetup when you started?

No, when I started, we used to all meet up at WordCamp San Francisco.

Got it.

I'm very extroverted. But I was so nervous, so nervous to meet new colleagues. I looked up to everyone so much. And one thing that I still laugh about and tell the story quite often, actually, I told Matt, I love everyone. I love everyone. And he just kind of looked at me and he said, you haven't met everyone yet. I said, I love them all anyway.

Just wait.

I know.

I was so excited.

It was a really fun time.

Thank you, Sherry. Hello everyone, Ben Huberman here. The GAAM Meetup is a huge undertaking that takes years to plan. We've heard from people from all over the company talk about what it's like to attend the GM. Now let's talk to someone who knows what it takes to actually pull it all together and make it happen. Hello.

Hi.

Could you tell us your name and title, please?

Megan Marcel, and I am an events wrangler on the events team at Automattic.

Could you tell us a little bit what an events wrangler does?

Sure. So, events at Automattic, an events wrangler ranges from everything from sponsorships to our internal meetups, and the biggest meetup being our grand meetup, which is when the entire company comes together for a week of team bonding and learning and just really the one time we're all together in person.

And when did you start getting involved with planning this event?

So I got started working on the Grand Meetup when I first got here. I got off the plane at the Grand Meetup and I was helping people get on buses. But really sticking to it full-time for the past 2.5 years and last year being the first that I completely owned the Grand Meetup, um, leading.

So I can imagine that people who've never been to a Grand Meetup might not have quite an idea of how complicated this process is. Maybe you can tell us a little bit about what this process entails.

Right now I'm starting to plan for 2021 locations.

So 2 years from now.

So 2 years from now.

But the real planning begins about a year out. We'll go to contract. Potentially earlier than that. And the real planning starts about 6 months out. That's when we start doing it full-time, all of the logistics from people getting visas to come to the Grand Meetup, booking flights, and then we start getting to the stuff about when they are actually on site.

How many people work with you on this? Because this is a huge undertaking.

It's a huge undertaking and And definitely not one I could ever do alone. We have 2 full-time folks that work with me on the Grand Meetup and then our extended team. So on site we have about 10 people dedicated to working on the Grand Meetup. And those folks will help a couple weeks out and get them all ramped up for what's to come on site. And so this way they can just really easily transition into the Grand Meetup once we're here.

Maybe one thing that I would be really curious to hear about is how you choose the locations. I mean, right now we are in Orlando.

So we want to choose a hotel that's able to accommodate us ideally for 2 years in a row because we try to go back to the same place 2 years. People who attended before, it's a little easier for them. And then us coming in to plan it, it's a lot easier because we have those connections with the vendors that we're working with. So everyone from the hotel to the AV team to transportation company, and everything in between. So making sure that they can accommodate us 2 years in a row, that many people, and we're also looking for a lot of meeting space. So also hotel rooms. So we try to keep everyone at the same hotel, just really creating our own hotel. We actually have our logo on the building this year of the hotel. So that's exciting.

It looks great. I know many people who listen to this could not have seen it, but it looks pretty fantastic.

Yeah, so we just try to, you know, incorporate all of that and just work with a hotel that understands we have a lot of different needs that we have to accommodate with people coming from different cultures. We have different dietary, so working with a chef that is really willing to work with us to make sure everyone's comfortable.

What are some of the most challenging aspects of planning the GM? I can imagine that, for example, working on the menus is one of them because there's so many parameters to consider. Are there some other things that we might not see that hard, but then in real life are super challenging?

Yeah, so for a couple of fun examples, um, my credit card has gotten declined many times when you try to order 600 yoga mats to do a breathwork session. Right before we were coming here, we were dealing with a hurricane and an airline strike, so trying to figure out how many people we could rebook on a flight for the very next week. We have to—

And just so, sorry to cut into it, but just to make sure that we know how many people are actually here right now.

We have 808 people here right now, not including speakers. So we also wrangle all of our speakers. So all of the programming, researching speakers, then connecting with them, contracting them, getting them here, doing rehearsals with them. And we doubled the amount of external speakers we have this year for keynotes. So we have 8 this year, and that's not including any of our workshop speakers who are coming in.

Do you have any kind of favorite memories either from— I know this Jam has only kind of started, but I don't know, from either this one or previous ones, moments where things kind of clicked for you and you thought, oh, this was all worth it. All my hard work has paid off.

Yeah, just seeing people, the smiles on their faces, the Small details, if someone's birthday is this week, getting them a birthday cake. It makes the world of difference when they're away from their families during this time. I would say being in a general session and having a speaker on stage where the audience is just completely connecting, and just the thank yous and people just being so gracious, and they're— everyone is really happy to be here and just making those connections and seeing people make those connections. Is just incredible and you see it. You see it in the hallways, you see it everywhere. Just making the culture of Automatic come to the hotel wherever we are, you know, it's automatic.

This is Ben again. Everyone at Automatic has their own experience of distributed life. Some of us are constantly on the move, others log into Slack from places like Tasmania or Uruguay or Nova Scotia. Some work from home where they might also take care of family members or pets. Others like me mix it up a little between our home office, our favorite café, or coworking space. But one reason the Grand Meetup is so special is that it gives us all a chance to learn from each other about what's possible once you join a distributed company. We were able to capture a few of these stories, so let's hear some of them.

So for the, for the previous 3 years, I was in a camper. I was on the back of a pickup truck and on the Pan-American Highway for the, for the most part. There were some diversions into Brazil, into a lot of Argentina. A lot of Bolivia.

So how does that even work logistically? Can you just like park somewhere, get internet, and then just do your work? How does it work in reality?

I mean, you know, this is the age of the internet. Anything is possible. There are apps. And so we relied on an app called iOverlander. And so this is this crowdsourced app, and it was people who lived lived this same lifestyle we lived, and they would drop a pin on a map and they would leave a comment like, this is a campground, uh, it has Wi-Fi, there's hot water or not, there's electricity or not, or what is the voltage. So all of this data is all right there, and then you can spend a little bit of time extrapolating all of that data and putting on a graph or a map or whatever So, and that's how we lived was off of this mapping out the route based on connectivity.

Okay, so I just joined a coworking space actually, and I don't want to go there often, but I want to go there sometimes so that I can be in a different space and have a different experience and have some more like working social time. I love-hate working from home because I'm extroverted. Love that I don't have to do a commute. Hate that I don't get to be around my colleagues more often. Not only that, remote, I hate that I can't go and see friends that I've made at the company in the city or in where I live or even like several hours nearby, right? There's friends from all over. So like the Grand Meetup especially is a place to connect and it's just really, it's really nice and really connecting. And it helps you work so much with people.

When I got here and everyone was like, "It's great because you can work in your pajamas if you want to," and like for the first 6 months I did. Like, I didn't have a dedicated office area and I just, you know, sort of got up and started working whenever I felt like it and finished working whenever I felt like it. And I found that that was not a good choice for me, especially in the work that I have to do. It ended up making me be less resilient, more reactive, and also And also, I had no concept of, like, when work started and stopped. Our brains compartmentalize the information that we need in various places, and so when I lived and worked and did all of that stuff all in the same area, my brain was like, "I guess we work all the time now, 'cause we work in our pajamas and we work on the sofa, which is also where we don't work, and so this is just what we do. We work 24/7, I guess." Yeah, it was a rough— first year for me, frankly. My first year here, I really felt like Automattic and Matt had made the wrong decision in hiring me because I was having so much trouble getting used to it. And so now I have a dedicated office and I have my work computer, which does not come out of my office unless I have to write. If I write, I go to a different room that has a taller ceiling. I can also explain that.

Explain that.

I'm gonna just tell you everything about how I I've hacked my focus. So I have found that when I'm in a room with a shorter ceiling, I'm able to focus better. But if I have to do creative work, I have to go— or rather, it is easier for me if I go to someplace with a higher ceiling because it frees up, like, it just changes this idea of what I'm doing. It changes how I feel about it. Interestingly enough, when I have to do really unpleasant writing work, which sometimes happens, I do that on airplanes, 'cause it's a very constrained space, but I'm like 30,000 feet in the air, and so I don't have any place to go, and so I'm very focused, but I still am able to get that really creative, generative feeling so that I can get the writing done, because I'm flying through the sky on a tin bus, you know?

So when you've got a tough, tough email to write, you'll just book a flight somewhere?

Yes, I do all my emails on airplanes. No, no, if I have a tough email to write, generally for an email, because it's that short, I will just get up and walk into the high-ceilinged room and then walk back to my computer.

Tell me about how you work at home and where that is and what your days look like.

My day is fairly structured in terms that I get up in the morning, I put the coffee on, and I change clothes. I don't work in pajamas normally, so like I have a ritual where I feel like I'm starting work. I'll hop online and check out things that people have messaged me about maybe overnight. My team is very geographically diverse, so when I come online in the morning, they've been working for several hours, if not longer. So I'm playing a little bit of catch-up, but I also don't let that be the focus of my morning. I figure out where am I, where am I most useful at this point in time? Because within maybe an hour or two, some people might be going offline. So there's very little chance for overlap with a lot of people on my team. About midday, it's when I usually try to get outside. I have ADD, attention deficit disorder, and I did not realize that until I started at Automatic. So one of the founding things that I realized for in order for me to be successful, I need to do some sort of physical activity at some point during the day to help reset my brain. And it feels like I've had a good night's rest. And it's like another cup of coffee, if you will, but it sustains me for the rest of the day. So, and then I don't feel like I'm trapped within the four walls of my office. So I'm also one of those weirdos that's out at -10°F in the winter going for a run just because the feeling of being outdoors is really what recharges me. And then I come back and kind of finish my workday. And sometimes I'll split it up and get some tasks done during the light hours. And then in the evening, I might catch up a little bit on the things that I didn't, that were maybe more things that maybe don't need my full concentration. Concentration.

One of the interesting things I've noticed is that Automattic has the ADDmaticians channel and neurodiversity channels for folks to sort of swap tips. You know, what are some things that have been shared among the group in terms of how distributed works— distributed work works for neurodiversity and for how you work with within that?

I think the, the big takeaway is that, like most people that belong to any type of unique group, if you have neurodiversity, it means a lot of things. Includes people on autism scale, or in my case, attention deficit disorder. It's, in my mind, it's a collection of things that you can't see that affect a person to see or feel the world differently. And so the biggest takeaway that I have that I've shared with other people is that you have to be responsive to your own signs of being overwhelmed. And you have to— self-care is a really simple way of putting it, but you have to develop a mechanism to address when you are feeling overwhelmed. And you— I try to lead my team with vulnerability, both for myself, and I try to encourage other people to be vulnerable. And I think that's what the ADDmaticians channel and being open about neurodiversity does, is that it establishes that we all have— I'm not gonna call them faults, but we have unique things about ourselves that are different, and you can only work better with people if you know what unique things make them different from yourself. And in my case specifically with ADD, if I'm having a day where I can't concentrate, it affects how I'm leading a meeting or how I'm having a broken conversation with someone because I'm doing several different things. And then I've asked people to call me out if they feel like I'm not giving them the focus that they need. So I've been very open with what— how my brain works. And if I tell people, "Look, I need to go out and go for a run," they know that I'm not just trying to get away from them. They just know— they know that I'm trying to be in the right moment or in the right spot for them. I don't know how I could do that without coming across as being noncommitted to the team, without telling them with honesty about what is going on in my brain. So, me leaving to go for a run doesn't mean that my running's more important them is I'm actually doing this to help me be a better team lead and a better coworker.

It seems to me overall that distributed work is a huge positive for those that are differently wired or operate different— just in terms of you're in control of your surroundings in a much more, a much deeper way than having to go into an office. Is that your finding?

It is for those of us that are fortunate to have the ability to have a quiet space or to be able to model an office that supports their needs. Like, I feel very fortunate that I'm in a place where I could buy a house that's kind of more suburb— or more rural, and I don't have a neighbor necessarily outside the window with a leaf blower. During the middle of the day. And I feel like, I feel empowered to be able to change things to make, make the environment as best as it can be. There's no requirement for me to have a certain chair or a certain desk. And granted, Automatic does give us the ability to buy a really great chair and a really great desk and have the computers that we need. So that, that eliminates that from being a concern, which is a huge deal for for me. Having a great posture and having comfortable things to work on, that's a majority of what I need. Previous jobs, I've worked in places where the air conditioning didn't work right, or one person was fiddling with the thermostat. Like, I have complete control over that. I can move the thermostat as much or as little as I want. Or if I'm having a day where I just want to go work outside, grab the laptop, as long as the Wi-Fi reaches, I'm good to go.

I've worked in high-stress environments my entire career. Being resilient no matter where you're working has always been very important to me, and this is a particularly difficult thing because when you work in a distributed fashion, and I work with the, the open source community, so volunteers also, like all three of the major risk factors for anyone working with employees come into play there. So you have to delegate things, and for volunteers, you're not delegating, you're asking them to take part in that. So you are delegating things, which is this huge level of risk. You have all these people that are far away from you, so you don't see them every day, and not only don't see them physically every day, but like, so often we lose track of them because your DMs close so that there's less noise, but then you forget to go and reach out. And so there's that one. And then of course the third one, which is the fact that we work in a cross-cultural space, not only geographically cross-cultural, but for the community itself, for open source WordPress, the differing cultures of distributed work versus co-located work. Those are massively different cultures. And if you're not aware of how that works versus this works, those two different entities, you never have any concept of how to invite yourself into the space in a way that works for both sides. And so, I spent a lot of time thinking about how to make sure that all of my teams are resilient, because we do really hard work on behalf of the community and on behalf of Automattic in the community. And it's important to me that they're happy and healthy and safe for as long as they want to work here.

So.

That's great. Can I ask you about Slack real quick? So, do you have Slack on your phone? Like, how— so, you talk about, you know, keeping your computer in a room and having set specific time in which work and personal do not overlap as much. How do you deal with that with your phone and managing your own phone time? Yeah. And asynchronous versus synchronous and—

Yeah. So, I feel like Slack has become the new email. So, there's that. And I do have Slack on my phone. I am in about 15 different Slack channels, Slack instances on my computer, but only 2 on my phone. One that is automatic and one that is the WordPress Community, not in anything else. It's specifically for emergency situations or when I know I have to be moving, but I want to be able to be available for people. I am incredibly aggressive with my do not disturb time. Like, it starts at 8:00 PM every night and turns off at 7:00 AM. 7 AM the next morning. And mostly it's there in case I need it. This is not for me to be a slave to that information. It's in the event I have to get it. And so there's that, but also I have themed days for what I work on and where, and also specific times of day where people can expect me to actively reach out and answer their questions. So at 10 AM and at 4 PM, I will go through and respond to any open questions that people have given me over the course of the day or the evening. And I have themed days. So Wednesday, I always do my community check-ins. I check in with all the team reps and— well, not all of them, as many team reps as I can get hold of. I check in with all of them all day on Wednesday. Thursday is a strategy day, and so everybody comes into basically a very long meeting with me where they can drop in and out and discuss strategy problems that they have. Fridays are when I follow up on everything that people need to be responding to me about that they've forgotten about. And then Monday is internal automatic days. Tuesday is external blocker for the community days. So, I don't know why I started with Wednesday and worked my way back around.

So you have not only worked in this structure for a long time, but you've studied it and written about it for a long time. What would you say— how would you say Automatic's distributed work model has evolved while you've been here?

It's super fascinating for me because I come from a background in consulting where I was actually helping enterprise and companies to work better together. And one of the first things I understood coming here is that the way Automatic was organized, even if at a smaller size it was, is that a lot of the practices inside Automatic at that small size were the same practices that I was trying to put in place for companies 1,000, 10,000 people large. So I was like, oh, that's interesting. They they're already doing all the good practices because working remotely forces them to. So that was one of the very first insights I had, because that also means that scaling stops being a logistical issue, a tool issue, and you can focus all your efforts instead on the people, on the leadership, on the processes. So all the things that instead are actually the problem between people that need to scale, you know? And I think that's one of the biggest advantages we had. And that hasn't changed it because we were, you know, we were 200 people, we were using certain tools. Yeah, the chat we were using at the time is not the same chat we use today, but it's still the same kind of scope and tool. The structure in that sense is still the same.

Now, given that you have studied this, written about it, consulted, What is Automattic doing right and wrong with distributed work? We must have some bad habits that exist that maybe frustrate you.

Yes, so let's start from the basics. What we're doing right is in terms of what is usually referred to, for example, as a flat organization, but we're not flat. So the way I would define this is that there is no boundary in contacting anyone in the company. I should probably find a better, like, more catchy way to say this, but so we have a hierarchy, but the point is not the hierarchy. The point is that I can reach anyone in the company at any given time, and I'm actually encouraged to do that if there is effectiveness. Yeah, again, you touched a topic that is not really about the tools, right? It's more about the culture and the interaction between people. And I think that there is a little bit of an obsession in this sense that, you know, oh, the company is failing because, you know, this information that I used to post before, everyone read it, and suddenly I have a problem because I don't know anymore where to post or where to discuss things. And but we grew, right? We are a larger company, and we all know from uh, for example, social psychology, that we can hold in our mind roughly 200 people, 250 people as our close connections. And of course, it doesn't limit to work, but let's assume for a second that 200 people is limited to work. Uh, now if you are a 200-people company, you pretty much know exactly where to send the right message to the right people. It's natural, it's implicit. You don't think even twice. Where you are a 500, 1,000 people company, 10,000 people company, suddenly you're like, oh, wait a minute, my information, how do you propagate? How to make sure that the right people listen to it? But this is not a problem solver with any tool. It's just a matter of scale. So shaping the channel, shaping the information channels is part of, in a way, the management, the leadership. That should act as a filter. And this is one of the reasons why I'm not a huge fan of flat organizations, because I believe that a structured organization, a hierarchy, works if it's a communication hierarchy. It doesn't work if it's a power hierarchy, but if it's a communication hierarchy, it's effective in helping convey this message.

Hi everybody, Mark here again. Distributed work is a mode of doing work, but it also changes the way we live our lives, and it expands the possibilities for work-life balance. Ben and I talked with some folks about what distributed work means to them, and some of the conversations that came out of it were pretty moving. Here's Ben speaking with Will Brubaker to start us off.

I mean, what are some of the other challenges that being part of a distributed team like yours bring into the picture that you wouldn't necessarily encounter if you were all in the same office?

Well, time zones is kind of the obvious, you know, when are people awake? And this is also very important to when can we have the best impact? You know, where are the people who use our product? You know, what time of day are they asking for help? What time of day do they need our help? You know, when do we need to be solving problems? So we have to balance all of that out between also our own needs because we do have— all of us have our own lives and we have people in our orbit, our spouses, our children, our parents, our our friends, our everybody. So we have to balance all of that.

Do you have anything, any kind of system or tools that help you stop work when it's done? Because one of the challenges of being a distributed team is that if you work from home, for example, your home and your office are the same space.

Boy, this is— yeah, your home and your office is the same space. And this is such an interesting thing. And also your question about how do you balance all of this. So it becomes a question of, do I work from home or do I live at work?

Is it still kind of a work in progress for you, or is it something you've kind of figured out by now?

You know, I'm very much in transition mode right now myself. Part of the changes that have occurred as the company has grown over the last couple of years is we have to be a little bit more rigid. We're covering a lot more ground, things are happening a lot more rapidly, We have to be able to react in a much more predictable way now. So I need to be able to say that next Tuesday, I am working from this hour to this hour, and I need to commit to that. So this has been a challenge to get there, but I also get to decide that. So if I need to move all of my work hours until in the afternoon so that I can do the things that I'm obligated to in the day, I can do that. When we were asked to start working weekends, and I was a little bit resentful about that, and I had a very, very strong team lead who supported me, and we ended up working out a really brilliant solution where now I am working every Sunday and I am happy about it, where I was digging my heels in against working weekends, but we found a way to make this work to my benefit, to my benefit, to the company's benefit, and it's a win-win situation. And this is the company that allows that to happen.

What are some of the benefits to being— you just mentioned a couple, but what are some other things that have made working for a distributed company better for you or for your life in general?

So to put it in the simplest of terms is I'm working for a company that allows me to be me. I believe that to be true across, across the board. And I look at people who wear onesies in cartoon characters and like, this is who they want to be. And everybody is really cool with that.

About us, there is a map where you can see all the heads of automaticians. I was the only one there in that super big island full of snow. Yes. Yeah, basically my husband got an offer, a very, you know, interesting professional experience offer, you know, to work there. And it was scary at the beginning, but we said, hey, you know, let's take the chance. Let's live the adventure and let's see how it is, right? There is nothing to lose. So I was working remotely at that time already, right? And living there, it was when I joined Automatic because for me it was clear, you know, I want to work remotely to be able to live there. And so for me it was awesome. It felt like, wow, I can be here, you know, in Greenland in this extreme weather, you know, situation or, environment, right? And to be working for a company that I love and doing what I love without a problem. And wow, wow, that's a big— that's a nice feeling. If someone wants to try to work remotely, I will say try. And don't expect people to be behind your shoulder checking what you're doing. Just be proactive on finding solutions, doing stuff, and, you know, asking for questions when you don't know how to do something. When you working remotely, it's very, very important to communicate as much as possible with your colleagues because it's the only way for you to say, hey, I'm here, and to learn from them. If you are in the office and you are new and you don't know things, you just turn your shoulder to the right and ask for questions to your colleague next to you, but you We don't have that when working remotely. So I will say, you know, if you don't feel secure about things, just ask. You know, because in this company, everybody knows that communication is oxygen, and we really apply it. Ask for questions. People are going to be helpful, and never, never feel ashamed of it.

As you can hear, there's so much more to distributed work than just hanging out at home all day. Here at Automattic, we try to find solutions that make our work more effective and collaborative, but it also allows us to tailor our own work and our environment based on how we're wired. My colleague Aaron Douglas has some great insights on this. Now, you, you wrote a blog post that made the rounds inside of Automattic and You can correct me if I get the headline wrong, which is basically how remote work saved my life, right?

Yep.

So tell me a little bit about that.

About 2 months in after I started Automatic, I was overwhelmed, and I knew that my brain works differently than a lot of people in terms of my focus and attention. It was never really an issue because I had ways of handling that, and actually working in a regular office where you're constantly being interrupted being asked to come into meetings, or the person next to you starts having a conversation, you're listening in. It actually worked really well with how my brain's wired. But then when I started working at home alone, it was really only my own mind defeating myself. So I had— it was all on me to keep that train going during the day. I didn't know how to cope with it though, and so I talked to my physician to say, "Hey, I think I have ADD. Like, I think I've had this all my life, but I've just never needed to worry about it." And so that sent me on a path of talking with a counselor and start developing a toolbox of things to help combat the issues I was having with focus. The frustration was pretty real, and I needed to walk away from my computer one day, and it was— I literally walked outside took a short walk, which is something I normally have been doing. In a regular office, you go for a walk during lunch and you come back all sweaty and you're worrying about smelling, and just, you know, not every place has a great shower room, and it just was a— it was an excuse for me not to do something more physical during the day. But at home, who am I trying to impress? Like, as long as I look presentable for a webcam, I can wait till midday to take a shower if I want to go for a walk. But what I realized early on is that when I came back from those walks, my brain felt almost reset for the rest of the day. And that turned into like a daily habit over time. And, you know, there's a lot of bits of story in between, but essentially I went from the occasional walk to riding my bike and then to doing running as well. And it's now a daily habit, and I feel strange when I don't have the ability to get outside and do that, that exercise, and it's, it's part of my toolbox. And before I started at Automatic, I was having issues with atrial fibrillation, and that is where the electrical system of your heart just goes wonky and it doesn't beat right, and the major issue with that is it can induce strokes, because when your heart's kind of in a stopped pattern and the blood's in an area where it shouldn't be, it can pool and form a clot, and that can go into your brain. So I was really scared when I heard that. So this— that combined with needing to be outside to help reset the brain was just kind of like a one-two punch to motivate me. My focus this entire time has just been on my focus, and the side effect is that I'm near— actually, I'm over 100 pounds lighter than I was before starting at Automatic, and I feel like even though I've aged, I feel like I'm healthier and I feel younger than I have, and I attribute a lot of that to Automatic and working remote and my coworkers for helping encourage me and finding friends to kind of just socially run with them, like Strava or Runkeeper or one of those, those services. That's, that's been a big part of what's kept me going, and now I'm returning the favor and also and also helping other people motivate themselves. So yeah, that's effectively how I think Automatic helped me save my life because I've gone from being dependent on medication for atrial fibrillation and feeling defeated to feeling fairly successful with my attention problems and being off the medication for my heart and overall just being in a healthier place.

Hey everybody, Matt Mullenweg here again. As Automattic has grown, so has the number of perspectives on the freedom, flexibility, and occasional challenges that come with distributed work. It's really amazing and humbling to listen to these stories, to be able to relive some of the magic of the grand meetup too. Thanks to everyone who shared, and to Mark Armstrong and Ben Huberman for for capturing these powerful stories. As you've heard, hosting the Grand Meetup every year takes a lot of work. Booking hundreds of flights and hotel rooms, the food, the speakers, it's a lot. But we think the value of the connections that people forge with their coworkers vastly outweighs the cost, which is now getting into the millions of dollars. This meetup and the smaller ones our individual teams have throughout the year are vital for a distributed company. On the next episode of The Distributed Podcast, I'm going to catch up with an old acquaintance of mine, Anil Dash. Anil is a pioneer who really helped define what blogging looked like back in the early aughts. He cares a lot about the web and about technology, the direction that both are going, and how they affect everyone. Anil runs a semi-distributed company called Glitch, which has developed a social platform for building and sharing apps. The team at Glitch puts lots of thought into creating a work environment that centers employee well-being, and I'm interested to hear how the company's decision to go distributed fits into their commitment to employee care. They have an office in New York as well as being distributed, which is also very interesting to me now having an office in New York with Tumblr. Thank you so much for listening and see you next time.