Joseph Stalin famously said, In the Soviet army,
It takes more courage to retreat than advance.
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The common reaction to an off-site retreat—whether spoken aloud or silently grumbled—is often, “Is this really necessary? It’s just a lot of talk and a waste of money. Can’t we do this at the office?” If the goal is simply to push through an agenda, then yes, stay at the office.
If the intention is to think bigger, reset perspectives, or foster deeper engagement, a retreat should be seen as an investment in the people and goals we claim to prioritize. From Michael Morris:
Sometimes organizations don’t want the conventional ways of thinking and the conventional goals of their organizational culture to be top-of-mind for people. When an organization wants to rethink its strategy or brainstorm about an entirely new business model, they almost always will hold an offsite meeting in some very different setting… a hotel in the woods, a mountain resort. It’s someplace very different from the office so that these everyday office frames and scripts are not top-of-mind, and we have access to other kinds of thinking.
A well-planned retreat doesn’t have to be a boondoggle. Facilitators can be brought in if necessary, and while some choose “fun” team-building weekends, the best retreats offer a relaxed yet structured environment to slow down, think, plan, and reconnect.
Our law firm decided to hold a partners retreat at a Kentucky State Park lodge, just an hour and a half away. The drive alone helped set a positive tone. Our meetings took place in the great room of a cottage. We ate together at the lodge restaurant, took breaks in the fresh air, and walked between the lodge and the cottage. Being in Kentucky, we may have included a little bourbon in the evening session… It was simple, yet the atmosphere and setting gave it a different feel—more strategic, more focused—than our usual weekly lunch meetings. It went well, and we genuinely enjoyed the time together.
I helped a consulting client organize and lead a two-day retreat in Chicago. His team was spread across the U.S. and internationally. Bringing everyone together was disruptive and expensive, but it was worth it. The retreat itself was productive, but the biggest impact came from physical proximity. Meeting in person, sharing meals, bowling, and just spending time together created a renewed sense of camaraderie. You could feel how much the team valued being in the same space.
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Down the hall from one another or across the ocean, a retreat can pull us together.
