How remote companies plan Team Retreats


It's tradition for most remote teams to pick one or two dates per year and meet in-person. Apart from some effective team building, that also means a ton of planning. How do you start such an operation? We've been looking at team retreats and are following some leading teams to see how they are doing it.

What is a team retreat?

A team retreat is an extended trip with your whole company – usually a few days or up to a week long – that is intended to build team culture, let people socialize and get to know eachother. While a common thing to do in many companies and teams, it's almost crucial to the culture of a remote team, due to the usual lack of casual conversation and private exchange.

Remote team retreats tend to be longer – often a week or more – and tend to include more work-related presentations and discussions, rather than just social exchange. As it is often the only time a remote team comes together in-person, it's a popular time for long discussion and planning for the mid- to longterm future of the company.

Depending on company, team retreats happen in different locations that are well accessible to the largest part of the company (e.g. US is often a bad choice for international teams).

What's happening in these retreats?

Retreat activities differ based on focus and company, these are some of our favourites:

  • Team excursions
  • "Unconference" sessions
  • Gaming and karaoke nights
  • Hackathons
  • Planning Sessions
  • Presentations about past work
  • Workshops & Learning Sessions

Of course, there is almost no limit to what you can do during this retreat. One thing to keep in mind: This is a special week, so don't strap people into tight deadlines. Give everyone the opportunity to enjoy themselves – it's just one week.

Learning it from the Pros

Quite franky, I haven't organized a full team retreat myself, so this post was heavily inspired by the work of some leading remote-first organizations. Let's look at how they do it.

Zapier: "Doing day-to-day work would be a wasted opportunity"

Zapier's piece is especially interesting because they have planned remote retreats with two employees to close to 200 employees. In this piece, they go over all the little details of what goes into planning and executing a successful retreat. This article is a must-read, but I had some favourite pieces nonetheless:

  • In terms of location, Zapier mentions that having a place close to an airport is a must. It does not need to be in a city (because there's rarely time to make use of all the amenities), instead there should be activities nearby: The beach, hiking trails, game room....
  • Retreats are expensive, but not as expensive as a team that doesn't work well together!
  • Getting feedback on the trip and iterate for the next one is useful

StackOverflow, Fog Creek & co: "Get face-to-face time"

The folks at have asked dozens of remote companies about their retreats and the responses – while not very detailed – are interesting to read nonetheless. A lot of it is duplicated, but some favourites:

  • Kin: "Consider having the whole team living under one roof through AirBnB"
  • StackOverflow: "We find a yearly all-team meetup is a good time to have year-in-review discussions about our culture and practices, with less focus on specific current projects."
  • Tortuga: "Please don’t spend your retreats sitting around a table looking at your laptops. You can do that the rest of the year."

Buffer: "Schedule 7 months beforehand"

Buffer's report on their retreats is – as expected – a great and very transparent view into planning a retreat for your remote team. If you've read the previous posts, you'll re-read a lot of stuff here, but there are some notable points to look at either way:

  • There's a distinction between work time and non-work time, even though it's much looser and more focused on collaboration.
  • Work-time is to get work done, have meetings, have discussions
  • Non work-time (evenings and weekend) are for excursions, spending time with your coworkers, having fun...
  • Retreats are one of Buffer's biggest expenses, expect to spend ~$5,000 per person on this!

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