Sunday, April 27, 2025
What is the difference between a successful retreat, and one that is… adequate? As a retreat leader, I’d like to think that the quality of the retreat leader (and the prep) makes a big difference, but there’s more to it. The most successful retreats get one thing very, very right: the balance between learning, facilitation, and relationship-building.

What is the difference between a successful retreat and one that is… adequate? As a retreat leader, I’d like to think that the quality of the retreat leader (and the prep) makes a big difference, but there’s more to it. The most successful retreats get one thing very, very right: the balance between learning, facilitation, and relationship-building.
Learning: The value of a training component is that it achieves two important goals: It introduces new concepts, and it builds a common vocabulary around these concepts. When everyone goes back to the office, there is mutual understanding on the subject matter, and a support structure around it.
Facilitation: The underlying assumption of any facilitated session is that “the answer is in the room”. Facilitating a conversation on a topic – whether it be in the context of strategic planning, addressing a major issue, or building consensus – brings the perspective of each person to bear on the outcome. It fosters understanding and builds buy-in.
Relationship-building: Spending time with colleagues outside of the day-to-day builds understanding, rapport, and stronger personal relationships. The payback on the relationship-building time investment accrues immediately post-retreat: improved collaboration, tighter alignment, and easier resolution on contentious issues. The dinners, wine tastings, and various other activities are not “perks”, but are examples of relationship-building activities: they are core to the event itself.
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So how do you get the balance right? It depends on your overall objectives, and who is attending. Here are some clues: If it’s a newer team, then lean into more relationship-building. If you’re looking to solve a specific problem and the team would benefit from new ideas, incorporate a bit more learning. And if you’re doing more planning, lean into more facilitation. But whatever you do, ensure that there is enough of each.
This week’s action plan:
Consider your last retreat: would a tweak to the balance equation have made a greater impact either at the retreat or afterwards? This week, craft a “mock agenda” for your next retreat/off-site to get the hang of balancing these three elements. And if you have a retreat on the books, you can do it for real. If you’re not sure you’ve got it 100% right, reach out to me at Request@RandallCraig.com – happy to answer your questions or share my perspective.
Leadership Insight:
Why not embed relationship-building directly into the learning and facilitation segments? Here are three ways to do this:
Training is delivered on a particular topic, and then break into small (facilitated) groups to explore the issue in greater detail. Working together in small groups builds great relationships.
If hiking (or walking) is an activity, pair attendees up, and have them tackle a specific topic while walking. The conversation will end up being wide-ranging, and ultimately will build a stronger relationship.
If there is car travel, have groups of 2-3-4 people travel together. Have them use any pre-reading as a basis for their discussion. Again, more relationship-building.
Related Post: Defining a Leadership Retreat’s Objectives
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