As an entirely distributed, remote team, getting together once a year is essential to our company operating at a high level. In Castos’ annual team retreats, we take dedicated time to deeply understand each other, get some time to celebrate the wins we’ve had in the past year, and do some heavy strategic planning for the next 12 months.
If it’s your first time organizing a remote company retreat, you may be wondering how to structure the retreat, where to hold it, what activities you’ll do, and how to make it approachable and accessible to all of your team.
We just finished our 3rd company-wide retreat, and in these three retreats, we’ve learned a lot, and I’d want to distill down the things that we’ve learned in organizing remote company retreats for distributed teams.
Location
Deciding where to hold your company’s annual retreat is a big decision. We’ve done this a few ways: either just before an industry conference or as a standalone event. More on this below.
If you’re going to hold your remote company retreat along with a conference, then the decision of “where” to hold your company retreat is easy.
If it’s going to be a standalone event, here are a few things we like to optimize for:
- Ease of travel: it should be in (or near) a large, international airport to maximize direct flights for our team members. This makes travel easier, and flights are cheaper.
- Convenience: Our team is pretty evenly split between North America and Europe. So the decision on a macro scale of where to hold our retreat is pretty split between those areas. But generally, we want it to be near where we all live, but in interesting places that everyone wants to visit.
- City or Country: All 3 of our team retreats have been in large cities (Berlin, Chicago, and Athens). But next time we’re going to do it in the countryside. Both options offer benefits and drawbacks.
- Lodging: Where you and your team will stay is a big decision. Do you want to all be together in a large house, or have separate living arrangements in a hotel? We did a large apartment when we were just 3 people, but now that we’re 9, we did hotels, and that feels like the right way to go at this size. Probably anything above 5 people, I’d do hotel rooms for each person individually. No room sharing, gross!
Timing
How long should a remote company retreat last? What time of year is good for your company offsite?
All good questions, and while I don’t have definitive answers that apply to everyone, here’s how we’ve approached it.
Early summer is a natural win. Kids are still largely in school, so there are fewer logistical considerations for those with families. Most locations are cheaper when it’s not the height of tourist season either.
The weather is warm, so you can enjoy time outside, especially here coming off the heels of Covid; we all enjoy some fresh air.
Duration
All 3 of our team retreats have been 2 full days, 3 nights. This is an OK amount of time, but I’d do it a bit differently next time.
I’ll break down the exact agenda we had for the last 2 retreats in a bit, but the short version is something like this:
- Day 1: Arrive, dinner together
- Day 2: Half day work, half day fun. All meals together.
- Day 3: Half day work, half day fun. All meals together.
So, it’s about half work and half play. Of course, since we all work together there are a lot of informal sidebar discussions that happen in “non-work” time. This is where the real magic of an in-person team retreat happens.
However, we’ve now consistently found that two days is just too short. Especially with half of our team traveling long distances, having a retreat only for two days doesn’t make the trip worth it.
So our next retreat, we’re going to stretch it out to be 3 full days together, four dinners.
Accommodations
In our first team retreat in Berlin, we were just three people. So sharing an Airbnb was pretty straightforward.
In our most recent retreat in Athens, we were nine people, and last year in Chicago, we were seven people in-person (a few couldn’t make the trip and attended virtually for the working sessions). At this scale, I think that a single apartment or Airbnb is just not feasible.
We all work remotely and are used to our “me time”, so having a place where we can all escape to in order to recharge is necessary.
Having a hotel with a good “common space” turned out to be hugely important. Last year in Chicago, we didn’t really have this, and wish we did. This year in Athens, we did…there was a large hotel lobby and a very casual bar/lounge area where we got together to talk and work. This was a game-changer.
With or Without A Conference
Two of the three company retreats we’ve done were just before WordCamp Europe. With our roots in the WordPress community and open source in general via our Seriously Simple Podcasting plugin, we like to attend this fantastic conference.
And doing your remote team retreat just before a conference is nice. It’s just one set of flights for both purposes, one hotel stay, and one change from your normal routine.
At our most recent team retreat in Athens, about half of our team stayed for WordCamp Europe. The rest wanted to get back to their normal routine, to their families, or just back to work in general.
For those of us who stayed, we had a really great time at #WCEU2023 in Athens.
But, being gone from home/family/routine for a week is a long time.
If I were just starting out, I would NOT do a company retreat around a conference.
It’s just a lot to consider all at the same time. Overall it takes some of the energy away from the conference if you do the retreat just before, so you’re not as fresh and energized for the conference.
Working Time
At each of our retreats thus far, we have followed a pretty straightforward formula for the day format: Half day of work, half day of fun.
And I still like this a lot.
Having two full days to work together, plus an icebreaker dinner the night before the first working day, is a good amount of productive time together.
In our most recent retreat, we decided that we’d like to experiment next year with a 3-day retreat and have less structured work (and play) time and more time just to be working together.
When you’re in person as a remote, distributed team, it’s hard to distinguish between Work Time and Play Time. Because of this, I think people sometimes aren’t sure what’s appropriate for a given situation. Is this the time to talk about my kids or my travel plans, or is this the time to dig deep into our product roadmap for the next 6 months?
Show And Tell
Something we made time for last year in Chicago was what I called Show And Tell.
In this, team members from very different groups (i.e. Support and Sales, or Development and Marketing) would get together and work on real life projects together. This cross-pollination of perspectives, ideas, and context did a LOT for increasing empathy between teams. When a sales person sits with a developer to see them debug code it makes understanding why features work like they do so much richer.
Fun Time
Our Fun Time has always been very intentional and usually revolves around something touristy, outdoors, and interactive where we can all be involved. A few examples of activities we’ve done as a team include:
- a ropes course
- an arcade game museum
- an escape room
- a baseball game
- a happy hour on a rooftop bar
- a walking tour
Most of the time we’ve had our Fun Time in the afternoons. This feels right, as we’re fresh and ready for work time in the morning, and can spend the afternoon blowing off some steam and hanging out together.
This is also a more natural transition into evening and dinner time.
Costs
You may be wondering: “Ok, great, sounds wonderful, but can we afford this?”
Our most recent retreat, in Athens, Greece for 9 people cost right around $25,000.
A few caveats and explanations here:
- I surveyed the team to decide together where we wanted to stay. We chose a place right in the action, more touristic than others. Because of this, it was a bit less expensive than some other nicer hotels that didn’t have a great location.
- Our retreat in Europe costs about the same as in the U.S. Our team is roughly split evenly (5-4) between being based in Europe vs. North America, the difference isn’t traveling costs, but local accommodations, meals, and on-the-ground expenses. Your mileage may vary here.
- 5 of the 9 of us stayed for an entire week to attend the WordCamp Europe conference, so accommodations are not strictly for the retreat but for the conference as well.
Team Building
Holding activities that organically allow team members to get to know each other is hugely important.
In some cases, I want this to be spontaneous and happen naturally.
Other times I want to spur this discussion through activities that I lead.
This year we did two things that I really loved, and were hugely helpful in this regard. All credit to my business coach, Mike Del Ponte for connecting me with both of these ideas. In some ways they really made the retreat for me.
Working Genius Survey
Created by Patrick Lencioni, the Working Genius survey is a fantastic tool for discovering where an individual’s strengths and tendencies are within a group. Understanding our team members’ underlying, natural biases goes a long way toward really understanding where they’re coming from on particular topics.
This gives us all the grace to recognize when someone is being a Wonderer and proactively seek opportunities for team members to embrace their strengths and truest selves.
5 Core Values
The 5 Core Values exercise took a list of core values from a James Clear blog post, and each team member wrote down the five most important values to them on an index card. At dinner one night, we went around the table and talked about why we chose the five values we selected and then which one was most important to us.
This got pretty deep, to be honest, and I was so grateful that we all felt comfortable enough together to be able to share some of these deeper emotions with each other. Talk about team building.
Getting Feedback
This retreat isn’t about me as the founder. Even though I’m the one organizing most of it, along the way, we try very hard to build consensus for where we’re going, where we stay, what we do, etc.
And that continues after the retreat is over. I send out a post-retreat survey for the team where I ask for their feedback on everything from the agenda of activities, the type of place we stayed, travel accommodations, and generally what folks liked (and didn’t like).
Getting async, written feedback like this from the team in the form of a survey is a great way to organize thoughts (and refer back to them) when it’s time to start planning next year’s retreat.
Considerations
In designing your remote company retreat, there’s much to consider. For many of us as company leaders, it’ll be the first time we got to play travel agent for so many people. And it’s a daunting task to have that one time of year that your entire distributed team can get together and really capitalize on that face-to-face time.
But, with careful planning, a bit of consensus-making between the team, and some wiggle room to let people explore on their own and just spend time working (or sharing a beverage) together, this could be some of the best days you spend all year.
