How to organize a retreat for a distributed team: 9 lessons we learned

The biggest challenge for a distributed team is to realize that all the people on the screen are actually real. For that reason, experienced remote workers like Buffer, Zapier or InVision come together at one location from time to time to work together and have fun. It makes their teams really strong, as people are not only coworkers but friends as well.

This year, the TRNDlabs team met up for the first time at a retreat. It was an amazing week that made us love our jobs twice as much as we did and laid the groundwork for many amazing ideas. Although it exceeded our expectations,  the retreat required lots of preparation. We’re sharing some lessons we learned here to help other teams organize a retreat.

Plan things in advance

Obviously, a retreat is not  a last-minute deal. We began with the idea as  much as 6 months prior to the event, and it was great!

TRNDlabs team working together

However, it’s important that you don’t start too early so as not to leave people hanging. Usually team members are looking forward to a retreat, and it’s not good to tell them about it for months with no result. Two to three months is more than enough to organize everything.

Involve team members in organization

If your company is rather small (we’re a team of 10), then make a list of tasks and assign them to different people. For instance, we had these main departments:

  • logistics (location, transportation)
  • food
  • activities

As a retreat is something people really look forward to, they’ll be glad to have a stake in organization. In addition, this collaboration helps to rally the team together before the retreat even happens. Every team member at TRNDlabs had their area of responsibility to make the retreat as great as possible.

For the first, do it at a familiar place

Yes, it’s tempting to travel to a place no one has been to (and it has its own advantages as well). But from our experience, we recommend choosing a location you’re familiar with, as you will be able to plan everything in detail and reduce many headaches.

Most of our team is located in the Netherlands, so we came together in Monnickendam, a lovely town near Amsterdam. We rented a hotel at a farm so we could spend time in nature without too many distractions while also having enough space for work, leisure and walks if someone wanted a little quiet time.

A distributed team coming together for a retreat at a farm

Stock up on the essentials

Double check the place where you work. Although Internet connection quality is obvious, it’s still something many places have troubles with. Make sure the place you stay at has stable WiFi for all your team members to be able to work at once.

TRNDlabs team working together at a retreat

Also, check if they have a coworking space, meeting room, projector for presentations and other small things you might need. Convenient transportation is a must as well.

Balance work with fun — but don’t mix the two

That’s an important thing we learned during our retreat. A retreat is not a vacation, but a time for working together in one place. We combined a few hours of work with a few hours of fun in our agenda and planned many meetings to get the most of our face-to-face communication.

However, it might be better to have separate days for work and spend weekends on sightseeing/leisure as it can be too distracting to mix them, and people won’t be able to get all the necessary work done.

Take time to talk about company mission and values

Everyone at one place, face to face?  Don’t miss this amazing opportunity to reflect on vision, mission, and values your company brings to this world. Have a collaboration session just for this so people won’t feel it’s something that comes from a top down, but they create and share it all together.

TRNDlabs CEO talking about company mission and vision

Combine different outdoor/indoor activities

Just like your work time, plan leisure time in detail. Eating breakfast, lunch, and dinner together are a good idea (and even better if you’ll try to cook together).

A distributed team at a retreat

Also, plan some board games, go fly drones, do cocktail parties, experience outdoor activities (like biking, football, sightseeing, and walks) or whatever people might be interested in. Encourage people to share their knowledge and to teach their teammates something new.

If there happen to be events nearby, feel free to attend. We went to a gym together as well and bonded even more.

Also, remember that no matter how often your team members travel (we have a few digital nomads on a board), they still need 1-2 days to adjust to a new environment and time zone and the activities on your agenda should facilitate that.

Explore cultures

Do sightseeing and experience typical local activities. Many people might be visiting a country for the first time, so make sure they won’t feel like they’ve seen nothing. We dug into the Dutch culture (even locals felt themselves becoming tourists for a while) by cycling, boating, attending local places and even taking a photo in traditional Dutch dresses.

TRNDlabs distributed team coming together at a retreat

Moreover, encourage your coworkers to share something from their cultures. We tried treats from different countries, cooked dishes from different cuisines and even had a Brazilian Caipirinha! There are so many things to learn from your co-workers.

How to organize a retreat for a dsitributed team

It’s not as expensive as you might think

Last but not least, some teams don’t do retreats as they think it will cost them a lot. Not only is nothing as important as the happiness of your team members (and therefore customers), but if planned well, a retreat doesn’t cost that much. People usually spend as much as they’re used to on a daily basis in their countries. And if you prepare in advance, even flights are can be affordable.

However, the most important thing we learned: a retreat exceeds any and all expectations. It rallies a team so much! We got to know each other a lot better, and our character and habits built great friendships. Take your time to think, plan, adjust — but do it and as often as possible.