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Successful Team Retreats

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Last week our team gathered together for a team retreat. During this retreat, all of us left our families and work priorities to spend a few days together to grow as a team, work on Soapbox, and be intentional about the culture we are creating at Endurance Learning. We are all sensitive to the sacrifice it takes to attend these retreats and place the utmost priority on making them useful and successful.

A lot goes into making retreats work. Let’s look at a few things our team does on our retreats to ensure success.

A Well-Planned Agenda

Every retreat should have an agenda planned well in advance and shared with the team. This includes logistics, time for business, and time for fun. We will dig into what is on the agenda in a moment. The key is that it is dynamic. Retreats don’t happen that often. When things are derailed, or tangents happen that are necessary, lower priority agenda items may need to move to a later time or off the agenda entirely.

Business and Activities

All retreats have goals, and those goals should strike a balance. I see this as a three-legged stool that balances business, work, and fun. On the business leg, take about one-third of your time for regular updates, state-of-the-company breifings, reflections on successes, and any other business information employees should be privy to.

On the second leg is work, and this can also take about a third of your time, maybe a little more. These are often break-out or group activities where employees have a chance to really dig into something they wouldn’t otherwise do. This may be a major planning session, an opportunity to work through a new product or feature, or a chance to get something done that has been waiting for such an opportunity.

The fun leg of the stool is just as important as the other two legs and your stool will fall without it. Fun activities at retreats build team collaboration and creativity, among other things. Some ideas to build into your agenda include setting up time at a board game cafe, designating teams for a Pecha Kucha night, a sunrise hike, or even just grabbing some ice cream and seeing a free concert in the city of your retreat.


Every year one of my colleagues asks me to reflect on my favorite part of the retreat. Every year I stumble to figure it out because so much happens in such a short time. This year was a little easier as we are so very close to releasing a full version of Soapbox, and it is easier to see how far we have come. I still appreciate this question and hope he never stops asking me, because it always changes.  Debriefing helps demonstrate the value of these retreats and reflects on what we have done better from years past.

Team retreats are a lot like training. With facilitators, activities, and a similar structure. What do you see that goes right, and what can be improved at these events? Let’s talk about this and anything else on your mind in the comments below.

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