An Automattic field guide to meetups

Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen.

Automattic has been a distributed company since the start. By now, we have more than 2,000 people who live and work from almost every corner of the planet. Part of what makes that work — and work incredibly well — is a commitment to getting together in person a few times a year. Here’s how (and why) we make that happen.

The what and why of meetups

What exactly is a meetup?

Take a team, division, or company of people who live and work distributed across as many as 97 different countries. Now bring them all to one place.

That’s it. That’s the recipe. A few times a year, a group of colleagues heads to a beautiful part of the world, meets face-to-face, and works on projects that are easier to tackle in person. Then they all head home with a renewed sense of focus and purpose. And possibly a suntan.

Why meet up at all?

Part of what makes the distributed model work so well is being able to bring together a diverse group of talented people without the false constraints of geography and time zones. Working remotely also means that Automatticians can live and work in whatever way fits them best as individuals. 

But face-to-face time is crucial for building relationships, understanding the nuances of how we communicate, and facilitating a different kind of creative collaboration.

Meetups get everyone on the same page. Breaking bread across a table builds trust and bonds that jumpstart relationships and drive momentum for months and years ahead. It’s a chance to make sure everyone’s on the same page and build a deeper connection with our colleagues. When we work together for the rest of the year, we bring a new level of understanding and empathy along with us.

Meetups fine-tune our mental models. Meeting in person is a higher-fidelity form of communication. Slack and Zoom are indispensable tools for distributed work, but even the world’s best webcam can’t pick up on body language, microexpressions, and other nuances of a face-to-face conversation.

When we interact with a person, we subconsciously build a mental model of them: a version of that person we hold in our minds. But a mental model is only as detailed as its input. If you’ve only ever worked with someone through video calls and Slack chats, your model of them is likely to be missing a bit of definition. Their personality might seem a little blurry, for example, no matter how closely you work together.

Getting together at a meetup, though, you finally get to see all of a person’s quirks and character in person. That contributes to a more precise and nuanced mental model — one that will enrich every interaction with that person going forward.

The three flavors of Automattic meetups

From getting 2,000 people to a single place to smaller gatherings of just 5 to 10 people, there are basically three flavors of Automattic meetup, starting with the big, annual Grand Meetup.

The Grand Meetup 

The Grand Meetup — the ‘GM,’ as it’s known — is a massive, all-hands company get-together that happens once a year.

The first GMs weren’t even called GMs. After all, it’s hard to describe something as “grand” when it’s small enough to take place around a kitchen table: The very first one, in 2006, was all of eight people in San Francisco. At our last full GM, in 2019, things had scaled up a bit, and more than 800 people got together in Orlando, Florida. (That one required just a touch more planning.)

It’s the one week in the year that almost everyone at Automattic gets together in a single place. The other 51 weeks of the year, we work from all over the world — 97 countries at last count

It’s also a chance to catch up with old friends, or even meet colleagues face-to-face for the very first time. We discuss our work, enjoy group activities, discuss our shared goals, and hear great talks from inspiring coworkers and outside guests.

We also lean into making cross-functional connections at the GM. Meeting up and getting to know teams you might not work with every day can spark new opportunities and ideas that you might never have considered otherwise.

It’s fun, it’s fast, and it’s somehow both energizing and exhausting. But above all, it’s an opportunity to learn from each other in an entirely new way. 

Division meetups

As you might have guessed, division meetups are a slightly more focused version of the GM: a couple of hundred people instead of some multiple of that. It’s a good way to refine the overall purpose, while still maintaining the energy and excitement of meeting people you don’t typically work with.

Division meetups happen once a year and are a great way to set division-level strategy, celebrate accomplishments, amplify work, and get everyone aligned on priorities and projects coming down the line. That makes for a solid blend of individual and team-level focus for each division. 

Team meetups

Finally, once or twice a year each individual team — generally 5-10 people, though some are larger — get together to plan ahead, realign priorities, work on a mini-project, and just spend time together somewhere scenic. 

It’s a very different scale of meetup, and can feel closer to a short-term house share than the more epic scope and schedule of the GM. We work, we walk, we talk, and we explore the sights and culture surrounding our temporary office.

How we do meetups

With 1,028 team meetups, 10 GMs, and 14 division meetups under our belts, spanning more than 13 years, we’ve learned a thing or two along the way.

Here’s how we roll.

Finding a place to make it happen

The size of your meetup is going to play a significant role in choosing your location and venue. But there are some basics that apply to pretty much any meetup.

Plan around international airports

Whatever size the meetup is, when your workforce is from all across the planet, it’s a good idea to look for locations that hit the sweet spot between inspiring and as close as possible to an international airport. That can save a lot of logistical chaos for people attending, as well as saving time and money otherwise spent on extra travel.

Smaller team meetups have more flexibility

For smaller team meetups, you have the flexibility of a short-stay rental or AirBnB. Team leads often take the reins finding a great spot for these meetups — after all, no one knows their team better than them.

The bigger the meetup, the more time you’ll need

When it comes to division-level and Grand Meetups, planning can span months and even years. 

Once you’ve found a great location, the heat’s on for your event planning team to scout and book a hotel that can accommodate everyone in your entire company – each in their own rooms. Keeping everyone at the same hotel can greatly simplify the programming, as well making it easier and more enjoyable for attendees; it almost feels like creating your own hotel for the week.

At least six months ahead of the first day of the meetup, you’ll need to book hundreds or even thousands of flights and hotel rooms while wrangling international visas. You’ll plan meals that meet attendees’ diverse dietary needs while starting to schedule events and itineraries for the week. Think you’re done? Wrong. You’ll need to ensure you’ve planned for everything, from good WiFi and sufficiently spacious meeting rooms to having 600 yoga mats or working karaoke machines.

Staying consistent can save a lot of headaches

For GMs especially, at Automattic we’re typically looking to choose a hotel that’s able to accommodate us for two years in a row. There are a couple of reasons for that:

  1. It can add a little familiarity for people, taking the edge off the potential stress of traveling across the world and jumping right into a packed schedule. 
  2. Compared to starting from scratch each time, you’ll already have connections with the variety of vendors you’ll be working with. Having figured things out with everyone from the hotel to the AV team to the transportation company can save a lot of time and wasted effort.

Making meetups work for everyone

When you ask that many people to show up in the same place for a week, having a schedule of events, activities, and goals for your time together can make or break the experience.

Some of the things you’ll want to consider to make sure everyone gets the most from the meetup are:

  • Making sure your location will be comfortable and safe for everyone. Along with prioritizing team-building, it’s important to approach planning your meetup with diversity and inclusion front of mind. Some locations may have cultural biases or laws that would exclude, threaten, or even criminalize LGBTQ individuals, women, folks with disabilities, or those in a perceived religious or ethnic minority. Inclusivity starts with ensuring that your meetup takes place in a welcoming and tolerant environment.
  • Treating accessibility as a first priority, not an afterthought. Ensuring that your chosen location is as accessible as possible, both in personal accommodations and group areas, is another critical part of meetup planning.
  • Protecting religious freedom. You’ll also want to ensure that the timing and location of planned activities don’t conflict with anyone’s ability to observe their holidays or days of observance.
  • Remembering that international travel is different after the pandemic. A lot’s changed since Covid-19 entered the picture, and it’s important to factor health and safety concerns into your planning and expectations of the people attending.
  • Considering neurodiversity, social anxiety, and fatigue. It may be uncomfortable or even overwhelming for some people to be in a high-pressure, high-visibility, or hyperstimulating environment. It’s important to keep that in mind when scheduling and planning your meetup itinerary. 
  • Scheduling with first-timers in mind. Such a massive undertaking and schedule can feel slightly overwhelming, particularly if you’re not sure what to expect. Giving people space, support, and an itinerary supportive of both introverts and extroverts can go a long way to making sure everyone has a great experience.