9 Things that Make a Great Team Retreat

Team retreats, especially in today’s remote-first and dispersed work environments, help groups come up with better ideas, facilitate important decisions, and build trust by preempting online personality conflicts.

Yet, we’ve all been to some really bad corporate retreats.

We’ve heard from tons of leaders in the past few months saying that they want to do more team retreats, but they’re not certain how to approach them. Below are the 9 things to focus on to organize and run a great team retreat.
1. Host it somewhere new. You want to take people out of the familiar to create good ideas and build richer relationships. There are thousands of interesting and unique hotels and alternative spaces like event and wedding venues that are inspiring by design. To get new ideas and levels of development, you want a place that is designed around authentic, “non-corporate” culture. Beyond that, you’ll consider whether you want an exciting (maybe exotic) location, one that’s easy to access, or a hybrid of the two.

2. Design for the outcome. What are you trying to do with this retreat? If everything goes as you hope for, what will it look like? Keep your goals broad, allowing room for change and new developments. Good outcomes are things like: “We have a product problem that has no easy solution – by the end of the retreat we want to have plan.” Or: “Business is good, but people feel disconnected and we see more interpersonal problems and miscommunication. By the end of the retreat, we hope to have built trust and understanding within the team.” With this, then, the retreat should be structured to allow situations where the group can collaborate and deliver on the outcomes. The best retreats deliver on objectives in ways you don’t expect.

3. Be thoughtful on timing and duration. What’s the best time for a retreat? It’s likely not during your busy season. It might be at the end of a major project or before one is ramping up. Ideally it should be at a point in your organization’s business cycle that it doesn’t put a strain on people’s work and comes at a moment of the most possible future impact. Three days (2-3 nights) seems to be the sweet spot for most groups to keep the retreat fresh and not burdensome, but to allow enough time to sink into the experience and get the most out of it. The timing and duration will, of course, also have a direct impact on your budget. Speaking of which…  

4. Develop a budget. Retreat costs vary widely. Once you’ve considered what you want to do, bring it to reality to consider what it’ll cost. There will likely be costs for venue, catering, transportation, and others. And there are two methods for doing this: (1) design to the budget, or (2) budget to the design. The former will reign in costs if times are lean, and the latter might deliver a better experience but with a price-tag that will get considerably bloated beyond expectations.

5. Get group buy-in. It’s essential to get participant engagement in the retreat itself, and that starts by getting participants’ input and guidance from the beginning. Consider sending around a survey to gather information or – better – conduct short interviews with people to gather feedback.

6. Someone has to be in charge. Once you’ve decided on the retreat design and structure, it’s important to delegate responsibility to a person or group of people to make it happen. There are tons of decisions to be made – big (e.g. venue, transportation, food, etc.) and small (e.g. notepads, pens, etc.) – and someone needs to be at the helm to make sure it comes together. Be clear on to what extent these people are gathering info to bring it to the team to make decisions and where they have free reign.

7. Consider hiring a facilitator. Whether training sessions or building social cohesion, having someone that has experience and is trained in retreat facilitation will help ensure the retreat’s success. Not only that, since they are outside the organization they will bring a fresh set of eyes without organizational baggage. You’ll engage the facilitator not only to lead the retreat (or portions of it), but also to advise on the retreat’s design and structure.

8. Schedule fun and free time. Even if the retreat is focused on concrete “deliverables,” make sure to allow for fun, spontaneous activities. Making it social and enjoyable will help deliver a good product.

9. Plan for the day after. In your retreat design/structure, make sure to plan for what happens the day after, the month after, the year after, and so on. Plan for how the retreat will actually impact the function of your organization going forward. And by all means design ways to get feedback on the retreat in the same way you got group buy-in. You might be surprised by things that went well and that didn’t, and this will help make future retreats even better. Need more help? TeamDays is here to provide end-to-end help in delivering a memorable, impactful team retreat.
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