How to Run a Company Retreat

By Wade Foster

You are reading: Chapter 5 of 15

Since day one Zapier has been a remote team. Now that we are up to seven people, 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 every 4-6 months.

Since we just completed our second team retreat, I thought it would be a good time to share what we've learned about how to run a company-wide retreat and get the most out of it.

1. Why should you do it?

Because the Marmot says so

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?

Mt. Rainier Company Retreat

Wherever you want!

For this latest trip, we chose an awesome five-bedroom home that overlooked Puget Sound and Mt. Rainier near Olympia, Wash.

We chose it for a few reasons:

  1. It was easy for everyone to get to, either by driving or flying
  2. It had enough space to hold everyone and then some
  3. The AirBnB listing looked amazing
  4. Close enough to some cool non-work related things we could do (Seattle, Mt. Rainier, etc.)

Ultimately, 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?

Cranking on day 1, maybe not so much on say 10

It depends. We did 10 days this last time around and it worked well because it gave us some time to do some work-related activities and some fun activities. It also worked well since our last retreat was five months ago and we'd added a new team member since then.

That said, you should be respectful of people's time. Many teammates might have family and other day-to-day activities they could be missing out on. I would never want our company retreat to cause marital strife or have some other unintended consequences.

One thing you can also do is setup the retreat so that if teammates have to join a day or two late or leave a day or two early it's not a big deal. That way you can get a longer retreat, but also not have to worry about coordinating tight schedules for a lot of people.

4. What should you do?

Zapier visits Startup Weekend HQ

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 did were 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.
  2. One evening after dinner we each went around and shared our story that lead to us working on Zapier. It helped create a shared sense of purpose that you don't get when you don't see each other every day.
  3. We hiked Mt. Rainer together. Doing something physical is also a great way to learn more about each other.
  4. We spent Friday night in Seattle celebrating Bryan's birthday.

We also spent time doing work-related things as well.

  1. We sat down on the first night and picked a shared project we could all work on and launch by week's end. We ended up shipping, which outlines one of the most common and easiest patterns to follow for adding webhooks to your existing API.
  2. We visited with some of our partners (shout outs to Stride, Smartsheet and Optify).
  3. We visited the Startup Weekend HQ office, which is the event where we got our start.
  4. We did super sprints on support to see how fast we could answer support questions when we had more than just Micah and a Dev working on the support queue at the same time.

After doing a couple retreats, I think the best retreat combines 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?

Cost of a Company Retreat for a Remote Team

Obviously cost is a big consideration for doing a trip like this. We have the luxury of generating significant revenue each month plus being well-funded so it made 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 way 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

Mike giving Bryan some feedback

Our latest trip to the great American Northwest wasn't our first company retreat. Our first company trip was in March during PyCon. While everyone had a good time, we learned a lot from post trip feedback. We used that feedback to make the trip to Seattle much better.

The feedback we got from our first company retreat during PyCon 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.

We definitely didn't get the same benefits from the trip in March as we did from our most recent Seattle trip two weeks ago. But in our quest for crafting the perfect company retreat, this time I posed the team six questions:

  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 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?

Here's what I learned about what we've got right versus what we can do better for our next trip.

Things We Got Right

We definitely got the cooking right

Based on the feedback from everyone on the team, here's what we got right this time around.

  • Don't skimp on the place—everyone was universally thrilled with the home we stayed in. The view was wonderful. There was plenty of space. The kitchen was great. A good place goes a long ways.
  • Cooking for each other was a big success too. Every single person mentioned paired cooking as being one of the most fun events of the retreat.
  • Sharing our backstories. As a remote team you don't learn all those little things about your co-workers as you might if you sit next to them and had lunch with them every day. Getting to hear the twists and turns that led everyone to Zapier was a lot of fun.
  • Talking about Zapier values. As a startup, talking about values can sometimes feel a little silly and corporate. As a remote team, it's nice to spend one meal talking about what we stand for so that when we add new team members we all have internalized the things that Zapier cares about.
  • Mix of going out and staying in. You can't work the whole time. Being able to mix up staying at the place and working vs. fun activities like hiking Mt. Rainer or spending the day in Seattle was a good call.
  • The length of time. I was a bit worried that 10 days might be a bit too long. Turns out 10 was about right, though I think 8 or 9 might be perfect.

What We Can Do Differently

Lets figure out how to get better

While I wish the trip would have been perfect (I'd give it a 90%), there's definitely a few things we're going to try to do differently next time around.

  • Scope back the team project as much as possible. Part of this was probably ambition. We all wanted to ship something big and awesome. But 10 days goes by faster than you'd think. And mix it even with the more team oriented activities like hiking and it becomes really important to scope out the project to work on. Next time we might try seeing how small we can make the project and possibly ship multiple micro-projects during the retreat.
  • Show off our work. One thing we didn't have a sense of was what looked like until it was almost shipped. Next time we'll likely do a nightly "show and tell" so we can see the progress being made.
  • A bit more planning before we get there. Our first afternoon we were there we planned out almost the entire week. This worked pretty well, however, a little bit more structure before will likely go a long way.


James dominated this trip

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.

Go to Chapter 6!


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