Reflections on meetups

A big perk of working for Automattic is the meetups. A couple times a year each Automattician gets the chance to meet up with colleagues in various places around the world. The location can be anywhere from Utah to Hawaii to Cyprus.

At the time of writing, I’m sitting on a flight returning from the annual Akismet team meetup. This year we chose Destin, FL as the location. Over the past week we have spent time invaluable time together, and I wanted to share some thoughts and experiences on what makes these weeks so special.

I won’t go into explanations on why meetups are an important part of the remote working culture, which you can read about from my colleague Steve (with plenty of other examples elsewhere). I wanted to dig deeper and hit a more personal note. Partly to share my personal thoughts with you, and partly because writing this down will help me to make sense of why they are important to me.

Meeting old friends

For me, when I get together with these teammates for a week it feels almost like a family reunion.

These are people I interact with daily, but just like in any office job you can’t know someone fully without knowing them outside the context of work. When you spend nearly every waking moment for a week with people you really learn a lot about them. You learn more about their personalities, their quirks, interests, passions, and life.

Think about how much better you got to know your college roommate than those friends you only saw in class and lunch.

Learning about what makes these people tick is much easier in a purely social context. Talking about life events builds a stronger friendship and social bond. This is really only possible when work is removed from the equation, and with an entire week to spend there is plenty of time that is exclusively social.

Making new friends

Since I’m an introvert, making friends is a difficult task for me. It takes a few meetings in a social setting for me to start opening up to new people. This face-to-face time allows for the natural, organic nature of friendship to form.

Previous office jobs I’ve worked have felt like forced friendships – “I work directly with these people so I should probably be friends with them.”

But I truly care for these people and am happy to call them my friends. I feel this is directly related to these meetups.

Working side by side

Besides the social aspect, it gives us the chance to work with each other in the same room. We split into smaller teams and work on projects for the week. The projects are meant to either launch by the end of the week or at least get a good head start.

Doing this helps to break up the everyday work and it’s a lot of fun. It also gives me a glimpse into the working habits of my coworkers. Everyone works differently, and that’s why the flexibility provided by a company like Automattic is wonderful.

I get to observe who likes to listen to music while they work, who prefers sitting at a desk or table and who likes to be on the couch. Some people are more productive in small chunks of time, others bury themselves for hours.

Spontaneous conversations

The team chats daily about our work and the big picture items that we typically don’t talk about as often. In addition, conversations about these things happen spontaneously when we’re all sitting in the same room. Something like this is hard to replicate with Slack or video chats.

Why is it hard to replicate? A simple answer: timezones. The Akismet team is spread out over multiple timezones in both the US and Europe. In order to have everyone present for a chat we need to schedule a meeting time that works for everyone. That sort of loses the spontaneity of in-person conversations.

And just like at a party, everyone is by default invited to every conversation within earshot. If I have something of value to add to a discussion that Anthony and Val are having, it’s easy and welcomed for me to interject.

What text and video chats lack

As mentioned above, some things are just not replicable. It’s also harder for me to get a feel for a person’s true personality.

Evidence of this comes from a statement by my newest teammate, Jamil, when asked how his first meetup was going.

I didn’t expect everyone to be so funny. On hangouts people just aren’t as animated.

So why do these digital communication methods lack the ability to wholly represent people?

Text chat

We use Slack as our main online communication. It’s great tool for keeping connected, but there are limitations to any text-based chat. Context is hard.

The biggest issue with text is the lack of inflection and tone. There is always a risk of something I say being taken the wrong way. For example, if I make a dry, sarcastic comment as a joke, it could easily come across as harsh or insensitive to those who don’t know me well.

Being able to put a face and voice with that little avatar staring back is also invaluable. I love it when I can hear someone’s voice speaking what they typed. Those avatars are also intimidating if you’ve never met the person. “What happens if I ask a question, will they be okay with me interrupting their work?”

Video chat

We use Google Hangouts every couple weeks to sync up about work we’re doing, team goals, etc. Jamil’s comment above is spot on. Despite being able to see their faces, it’s still hard to get the full picture of someone’s personality.

Right now I can only speculate as to why this statement is true: video chats can be seen as a business meeting. Because we need to schedule time on the calendar, there’s this subconscious feeling that it must remain (relatively) professional.

That’s not to say we don’t joke around or have fun on these video calls. But it’s far less than we do when we’re all together. Maybe it’s because we like to set a time limit so we don’t inconvenience everyone. Maybe it’s because at the meetups we know we can pick up the discussion later if it digresses into jokes and other subjects.

Sustaining momentum while working alone

While the week itself is great for building strong work and social bonds, it’s also beneficial for when we all return to our corners of the world.

With a better personal connection, I can anticipate how someone will react to something I say, whether it be a question or joke. When I understand their personality, I have a frame of reference for what they’re trying to communicate through text. Before meeting my teammates for the first time I felt like I was working in solitude because I had no real concept of their characteristics.

Ultimately, it makes working with my team much easier, productive, and a more positive experience.


  1. I think a big part of the humor thing in-person is timing. It’s a lot harder to joke around and play off each other when there’s a delay and it’s hard to hear over one another. 🙂

  2. Levity is the name of the game… Great post. Sounds like more frequent meetups would be beneficial. Perhaps Slack, Hangouts needs some kind of built-in humor indicator, set by the user.

    1. Thanks for the comment, Brian!

      Levity is the name of the game

      Beautifully said.

      It’s a delicate balance with the frequency of meetups as far as the benefits go. Travel and recovery time are something to keep in mind, especially for a team like ours that is pretty spread out. Too many meetups and the cons of travel and recovery could outweigh the benefits. Plus, it’s tough for those of us with families to be away from home more than two or three weeks per year.

      However, there are some teams that are planning to start experimenting with remote meetups in which they’ll block out time wherever they are to work or eat with an active Hangout session. I’m interested in seeing how those experiments go.

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