The One Thing That Makes—or Breaks—Your Strategic Retreat
After leading many strategic planning retreats across sectors - public, private, and nonprofit - I’ve come to a conclusion I didn’t expect when I started doing this work decades ago:
The secret isn’t a smarter framework or the “perfect” facilitator. It’s caring.
Not in the generic, feel-good sense. I mean the kind of caring that gets you to ask:
“Why are we doing this, and does it really matter?”
Strategic retreats are expensive - not just in dollars, but in time, energy, and attention. They pull the team away from the day-to-day fires and force everyone to slow down long enough to think. If there’s no genuine connection to purpose, then no agenda, flip chart, or buzzword will turn that time into something meaningful.
I’ve seen this firsthand. I’ve also had to learn it the hard way.
When participants show up out of obligation, you can feel it. The conversations stay shallow. The insights sound familiar. And the strategy, if one emerges, rarely lives beyond the binder it’s printed in.
But when people show up because they care - about the mission, the moment, or the opportunity to reset - something shifts. The room comes alive. People take risks. Even disagreements become productive. And that elusive thing we all say we want from planning – alignment - actually begins to emerge.
This doesn’t mean a retreat should turn into a therapy session. But it does mean we have to design these experiences with intention. We need to ask the hard questions early. Create space for honest reflection. And invite people to bring their full, invested selves - not just their titles.
Leaders, this starts with you. The tone you set shapes everything. You don’t need to have all the answers. But you do need to care enough to make the questions matter.
So, before you lock in the venue or finalize the agenda, I’d offer two questions worth sitting with:
Do we know why we’re doing this?
Do we care enough to make it count?
If the answer is yes, everything else gets easier. And the strategy you build? It might actually stick.
If you’re thinking about how to make your next retreat meaningful, I’d love to hear what you’re wrestling with. Sometimes a good conversation is the best place to start.