Organizing a Successful Team Retreat: The ClaimCompass Way

Are you thinking about organizing your own team retreat? The ClaimCompass team is back from a second successful one, with some tips for you.

Organizing a Successful Team Retreat: The ClaimCompass Way

January 2018. The ClaimCompass team had just returned from our first big retreat. While team members were sharing pictures and discussing how fun the whole experience was, there was one main question on everybody’s mind. When are we organizing the next retreat?

If you’re familiar with the words “team retreat”, you’ve probably heard them in the context of remote distributed teams of companies such as Buffer and Zapier. At ClaimCompass, we believe that every company can benefit from the opportunity to come together and bond as a team, even if most of our team members spend the whole year in the same office.

So, a few weeks ago, we embarked on a new adventure - our summer retreat in Greece.


For us, the team retreat stood for: celebrating togetherness and team bonding, communicating and collaborating with colleagues you don’t usually work with, aligning everybody on vision, goals and culture… while also having a ton of fun.

Every company has an unique and different culture, which goes to say that there’s no right or wrong way to think about organizing your own team retreat. Here’s a few tips from us at ClaimCompass:

The location of the team retreat


While some teams may be happy with simply hosting an office party or organizing a team building activity for their employees, the companies that choose to do a team retreat take things to another level.

They understand the importance of creating a setup where team members can distance themselves from day-to-day working life, enjoy some time getting to know each other and even exchange ideas and thoughts on the company’s goals and future. What better place to do that than a location far away from the office, like a cabin in the mountains or a beach house?

As a relatively small team, we decided to rent a private house on the beautiful Greek coastline. While hotels can feel quite sterile and boring, we thought a big standalone house would be more inviting and would give us the privacy and space to host all the activities we had planned. We chose a remote location close to the beach and nature rather than booking our accommodation in a bigger city.

The duration

For us, the perfect formula turned out to be: a weekend of relaxing, games and fun + two and a half days of work-related sessions, lightning talks and co-working.


One lesson we learned from our previous weekend-long retreat was that we simply couldn’t fit all the activities we wanted to in such a short time. As it turns out, getting up for a Google Ventures-inspired design sprint at 10am was quite hard after wrapping up a karaoke party in the early hours of the night.

The program

It can be easy to default to doing the things you always do on a day-to-day basis during the working days of the retreat, or to simply put “party hard” on the weekend todo list. But that would be a waste of opportunity!


For our summer retreat, we had the following goals:

  • Give team members the chance to learn more about each other
  • Create an environment where team members can collaborate on projects that are not necessarily related to their daily tasks, but advance the work of the whole company
  • Bring everybody closer together through memorable experiences

Here are a few of the items on our program that helped us achieve these goals:

The fun activities

We went to the beach, had a water fight near the pool, sang karaoke and shared delicious Greek meals together.


The get-to-know-each-other games

We prepared a ClaimCompass trivia game where team members had to answer questions about each other and the company. Nothing could top the unplanned deep late night conversations near the pool though!

The non-tech hackathon

Just like a hackathon… for people who can’t code. We used Zapier to come up with projects for two challenges (a productivity one and a fun/crazy one). One team created a solution that detects a conversation’s language on Intercom and assigns it to the right person. As our website supports 11 languages, that sure was helpful for our support team! Another team came up with a way of automatically archiving cases of users who submitted a double compensation claim for their disrupted flight. We also had a team that created a zap triggering a weekly newsletter informing team members about company events, birthdays, as well as their available vacation days or learning and development credit.


Celebrating ClaimCompass’ birthday

As our company turned 3 years old this July, we hosted a cake making competition and announced a final draft of our company’s values.

Lightning talks

From the always-so-relevant topic of Growth to specific talks on compensation claim processing - we used the time we had together to showcase what we’re working on and to share ideas.


The logistics

If you reached this part of the article, you’re probably wondering how much work goes into the organization of a retreat for a whole company. That can vary a lot depending on your team size, the retreat location and duration.

You may have a dedicated team member taking care of the retreat part or full-time. Their tasks would include location scouting, booking accommodation and transport for everybody, planning activities, ordering company swag, grocery shopping for drinks and snacks, picking the restaurants to have meals at, making sure the coworking conditions are fine etc. That’s a lot of work and it has a great impact on the whole event!

As we didn’t have a team member whose job would include taking care of the retreat back when we started organizing it, we decided to crowdsource the whole effort. Everybody took ownership in a specific task or joined a team like “House & beach”, “Food” or “Coworking”. We coordinated our efforts on slack:


And we used Trello to keep track of the work-in-progress program and responsibilities:


Some things to consider before you go off to your team retreat

As mentioned, no two companies are alike. Your team members are the best people to decide what kind of a retreat would make sense for you, how much time should you spend together and what the program should be. Take into account your company culture and tailor the whole experience to it.

Make sure you manage the team’s expectations on the retreat’s purpose and program beforehand. It’s best if every team member is given the chance to contribute to the event with ideas.

Successful or not, once the team retreat is over you need to collect feedback. At ClaimCompass, we asked our team questions like “What did you like most/least about the retreat?”, “Is there something you would change?” and “Do you have any thoughts on the location/duration/program of the next retreat?”.

Doing a company-wide retreat is a huge event that requires a ton of preparation, but it’s a lot of fun.

Over to you: get in touch if you have any questions or leave us a comment with your thoughts.

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