The worst kind of retreat is the one where everyone smiles in the group photo, but nothing changes when they return.
That’s the trap most leadership offsites fall into: scenic views, packed agendas, and surface-level conversations that never lead to traction.
Heather Roose sees this all the time. She’s not just a retreat enthusiast — she’s a steward of a 50-year legacy at Wingspread Retreat & Executive Conference Center, where the Johnson Foundation has spent decades mastering the art of alignment.
Wingspread isn’t just scenic; it’s strategic.
With experience designing spaces for real conversations and real outcomes, Heather shares what makes Wingspread’s retreats more than just “offsites.”
Spoiler: It’s not the snacks.
We’ve all been there: a retreat that promised clarity but delivered confusion. Leadership retreats too often feel like adult summer camp — packed with activities but light on impact. There’s plenty of trust falls, yoga mats, and scenic overlooks, but not a lot of action to bring back home.
Heather puts it plainly: “It’s not just the change of scenery that’s important, but an intentional design.”
Wingspread retreats don’t just plop you into a pretty place and hope for magic. They engineer the experience with a clear purpose: meaningful dialogue, aligned outcomes, and yes — a walk in the woods, too.
Too many teams spend their time dancing around the real issues. They talk about initiatives without addressing misalignment. They brainstorm without direction. They debate without action.
Wingspread doesn’t allow that.
“We have our convening model — the candid dialogue between people. They’re away from their regular lives so they can have that candid dialogue,” Heather explains.
This isn’t Kumbaya in a conference room. It’s structured time for unstructured truth. Real conversation, held in a real space that encourages reflection and candor. No buzzwords, no PowerPoint roulette — just humans hashing it out.
At Wingspread, the goal is clear: “There’s a commitment to actionable outcomes,” Heather says.
Translation: You don’t leave until you’ve decided something that matters.
The retreat model is built around three things:
Teams don’t just “connect” at Wingspread. They reset. They realign. They walk out not only with shared understanding but with a plan in hand.
There’s one more ingredient: wellness. Yes, you’ll get honest. Yes, you’ll talk strategy. But Wingspread doesn’t separate personal well-being from professional clarity.
Heather says it best: “Not just the honest communication and people getting to know each other, but the wellness component.”
Because when people feel good, they think better. When they slow down, they speed up later, with more focus, more cohesion, and more clarity.
If your last retreat ended with confusion instead of cohesion, maybe it wasn’t the people — maybe it was the plan. Wingspread’s 50-year track record proves it takes more than Post-its and platitudes to create alignment.
It takes intention. It takes honesty. And sometimes, it takes unplugging.
As Heather Roose shows us, when you mix thoughtful design, honest conversation, and a dash of nature, magic happens — not in the trees, but in the traction you take home.
Ready to ditch the retreat rinse-and-repeat cycle?
Let’s talk about designing one that gets your team aligned — for real.
