How to Run a Company Retreat for a Remote Team

This chapter is based on the current Zapier team size of 20. A previous version exists that reflects the operations of Zapier at a team size of 6.

One of the downsides of being a remote team is that physical interaction doesn't happen unless you make a dedicated effort to get the team together.

While we are firmly of the belief that day-to-day work does not need to happen in person, we do believe that there are some things that happen easier when in person. Because of that we try to get the whole team together for a company retreat twice a year.

We've now run five company retreats. Here's everything we've learned to pull them off.

1. Why should you do it?

Big, full-company retreats can be tough to coordinate and can cost quite a bit of money, so why even bother?

Ultimately, because some things are just better done in person. For instance, it's hard to have a casual conversation with a teammate over Google Hangout about their kids, shoot the breeze about some random idea you've had improving a secondary process in the company or sit down and talk about company values. All those things tend to naturally happen in person, while they don't happen in a remote team, unless you force it.

Also, it's a ton of fun. Since you don't see everyone on a daily basis, it's a ton of fun to actually have everyone around for a week-long excursion where you can chat shop and learn more about each other as people rather than the person on the other end of that avatar you see ever day.

2. Where should you do it?

Wherever you want!

We've had retreats in California, Washington, Colorado, Alabama and Utah.

That said there are a few things to consider:

1. Make it somewhere easy for folks to get (i.e. less than two hour drive from an airport).
2. Go somewhere that can hold everyone. We've done AirBnB and HomeAway houses. Hotels feel sterile, but houses feel inviting. Get a really big house that folks couldn't normally afford on their own.
3. Don't worry so much about being close to tons of activities. We used to think having a really active city nearby would be important, but then realized we rarely took advantage of the full city amenities.
4. That said, do have some activities very near the house. Beachside houses or houses with big games rooms (pool, pingpong, etc) are great because people can entertain themselves in downtime without driving places.

Ultimately though, go with what suits your company. I know some companies travel overseas or some bring everyone into headquarters.

3. How long you should do it?

It depends. You need to be respectful of people's time. After some iteration we've found five full days bookend by two travel days to be a good fit. People with family and kids aren't too inconvenienced and it's long enough to do something meaningful.

As you grow another thing to consider is staggering travel days. We have the founding team plus international travelers come in a day early and leave a day later. This means customer support for Zapier isn't abysmal for one day while everyone is traveling, since we're there a bit early we can prepare the location with food and since we're there a day after we can make sure to clean up.

4. What should you do?

It can be easy to default to doing the things you always do on a day-to-day basis at work. But that would be a waste of an opportunity.

We decided early on that we should do things during the week that we can't do together—even if it was at the expense of making progress on Zapier itself. After all, we work on the product every other day of the year. For one week it makes sense to take some time off and work on the team which is just as important as the product itself.

Some of the best activities we do are mostly unrelated to work.

1. We randomly paired people up each night of the week to prepare dinner for the others. There's something special about cooking a meal for your teammates that helps you learn a lot about one another. This has been a staple at Zapier retreats.
2. We play Mafia which is a great party game.
3. We've hiked Mt. Rainer, skied, swam in the ocean, and visited the USS Alabama together. Doing something physical is also a great way to learn more about each other.

We also spend time doing work-related things as well. The best format we've found is to pair a mini-conference with a hackathon. Here's how it works.

1. You'll have 4 work days. Split these days into themes (i.e. support, marketing, product, team).
2. Each morning have a few members of the team give 15 minute talks on something related to that area of the company. A good format is: here's what things used to be, here's where we're at now, here's what we're shooting for.
3. Do Q/A after the talks.
4. In the afternoon split into cross-functional groups and build something small (a prototype, an internal tool or maybe a real feature) that helps the team in some small way that's related to the theme day.
5. Re-group around 5pm and do demos about what was built.

After doing a couple retreats, the best retreats combine something everyone on the team can work on in person along with multiple activities that help the team get to know each other better.

5. What about the cost?

Obviously cost is a big consideration for doing a trip like this. We have the luxury of generating significant revenue each month so it makes it easy to splurge a little (we paid for the whole trip including plane tickets for all our teammates).

Also, a typical remote team saves tons of money each month by not having to pay for an office or paying for a much smaller one than you'd normally have to have. We decided to pour the money we save on office-related expenses into the trip.

The total cost of the trip wasn't cheap, but what's even more expensive is having a remote team that doesn't work well together. Ultimately, the cost of the trip is well worth it in my mind, but you have to make that choice based on the constraints of your own business.

Getting Feedback on the Trip

If you're planning to keep doing retreats as you grow then you'll want to make sure the retreats keep getting better. The way to do this is to ask for feedback.

For example, the feedback we got from our first company retreat was that since we paired the trip with a conference, everyone spent a ton of time doing their own thing at the conference and by the time we all were able re-group at the place in the evening everyone was really tired. So we decided not to do retreats alongside conferences again.

Here's some questions that are useful to ask the team after a retreat:

1. What was awesome about the trip? Be as detailed as you'd like.
2. What should we do differently the next time around? Be as detailed as you'd like.
3. In retrospect, are you glad we focussed on the projects we did or do you think a different project (or the same project structured differently) would have been better and why?
4. How do you feel about the length of the trip?
5. What dates are you NOT available between January and March?
6. Any preferred locations for next time around?

Conclusion

Doing a company wide retreat is a big event, but it's a lot of fun. If you run a remote team, I would highly encourage you to consider planning one for the next year. I think you'll find it well worth it and your teammates will love your company even more for it.

Curious what a remote team looks like in day-to-day action? In the next chapter, we'll peek at the Zapier team's workplaces, favorite tools and music, and more.

Go to Chapter 9!

Written by Wade Foster.