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Photos of a trip to Florida and some general thoughts on company retreats


Our company went to Florida for our annual company retreat. I'm still not sure how I feel about them.

For companies like ours with a large number of remote employees, a retreat is a chance to change up the routine, break out of the video calls, bond a little, and smell those you haven't met in person.

The basics of the retreat are simple: we rent a few houses somewhere in the world and fly everyone there to live together, usually for around 7-10 days.

Our first retreat in 2013 was in the Bahamas, then Spain in 2014, then this was our second in Florida.

When I tell people about our retreats, I'm generally met with envy. "Oh wow, how can I get a job there!" is a phrase I've heard more than a few times.

But are they good things, either from a personal perspective or a company one?

Importantly for the former -- they aren't a vacation. You're working. Nothing wrong with that, of course, but you're working away from your usual setup. For those of us who work from home it can be a bit off-putting. Easy-to-prep food, family support, routine and the multiple screens of a home office are the cornerstones of remote work productivity.

I struggle to be as productive on a 13" laptop on a wobbly chair at a dining table in a rental home.

And yet, it's a damn nice change of pace when you spend way too much of your life in one place.

[caption id="attachment_957" align="alignnone" width="640"] You forget, after a long winter, what the sun can actually do to your mood.[/caption]

They're also usually somewhere sunny. Sun and warmth, especially in February, is something you want to get out and enjoy.

Focus can be a challenge. We were, afterall, next to Disney World.

We didn't go to Disney World but I did have to go to the Kennedy Space Center:

[caption id="attachment_947" align="alignnone" width="640"]Space Shuttle Atlantis' Nose and My Nose Space Shuttle Atlantis' Nose and My Nose[/caption]

[caption id="attachment_949" align="alignnone" width="640"]rocket boosters saturn V Saturn V Stage 2 Boosters[/caption]

[caption id="attachment_950" align="alignnone" width="640"] Rocket in the sun[/caption]

So it can be hard to focus and get real work done.

On the other hand, you can't replace the in-person factor. Even meeting up once or twice a year strengthens relationships and makes everyone more empathetic, more open, and better at communication.

Solid communication is what remote companies live and die on.

[caption id="attachment_953" align="alignnone" width="640"] Dave, Andrew, Nicolas and Hugh laughing about code or something.[/caption]

For me personally, the sun and I are not friends. I also don't swim. So I'm not tempted to spend much time outside when we go to a warm, beach-adjacent locale. I'm usually the one who stays at the house while everyone else goes on an adventure. No problem, perfect time to focus and get some work done.

[caption id="attachment_952" align="alignnone" width="640"] Rainy day poolside. Another great time to get some work done.[/caption]

[caption id="attachment_951" align="alignnone" width="640"] My feet in our pool. This is as close as I get to water. [/caption]

So there's a lot of value in the face-to-face aspect of a retreat.

But I'm not convinced a company retreat is a great place to get work done, even if it's where I've done some great work myself.

My opinion is still open on their place in the remote culture. That's good. Remote companies, after all, are still very much in the experimental stage. And what works for one won't work for others.

We should always be changing it up to see what works best.

[caption id="attachment_954" align="alignnone" width="640"] We played a lot of Secret Hitler.[/caption]

[caption id="attachment_955" align="alignnone" width="640"] Everyone's a fascist (in the game)[/caption]

One thing I've noticed is that the organizational / logistical challenge increases as team size increases. Four people in an early startup phase can get up and go on little notice. Ten takes a bit more. Fifty people, no matter how much you plan, will be hard to get all together at one time.

A lot has been written about the optimum team size being somewhere around 5-8 people. Perhaps team retreats of that size are the best balance. So instead of sending the whole company at once, you chunk it up. This could also give the advantage of more exposure to any C-level or other managers that are normally split between teams on a retreat.

Does remote make sense?

I go back and forth. I've had great experiences with our remote teams. Lots of great software and companies are built by remote teams. But there is something intangible about co-location.

There's a sweet spot between full-remote and 9-5. The "local remote" company. That is, everyone is in the same town (or same area, with a few hour radius) but everyone works from home most of the time. Keeping everyone relatively close, even if it's a 2-hour train, means you can get together enough for meetings and drinks and meals while keeping the main productivity remote. Office optional.

I haven't heard of that model yet, but I'd be interested to hear about anyone trying it.

I know for me, I live just a short walk from the beautiful Crew Cafe, but I still work from home 90% of the time. I get more done.

But I also know what a god damn good time we had in Florida. Partly because it was an escape for all of us.

So the perfect remote work company structure still needs more experimentation. But at least we do know it's a step-up from mandatory office attendance.

[caption id="attachment_956" align="alignnone" width="640"] End of trip meal. Note the sweet potato covered in caramel and marshmallows.[/caption]