By Christine Courtney
Why plan a leadership retreat or team offsite?
Because when done right, a retreat isn’t a break from the work—it’s an investment in the work. It deepens connection, clears mental clutter, and realigns people around purpose. And no, it doesn’t require a private jet or a mountaintop resort. What it requires is intention.
If you’ve been feeling disconnected from your team, hitting roadblocks in collaboration, or simply craving a reset—then yes. Your instinct is probably right. A well-crafted retreat can spark ideas, strengthen bonds, and shift energy in ways day-to-day work cannot.
Don’t begin with the venue. Start with the outcomes. What will success look like? Then build backward from that “super-objective.” One year, our theme was “buoying each other”—and the whole retreat flowed from that vision.
Ask team members what they need most from this time together. Let them co-create the agenda, the swag, the experiences. People support what they help build.
What your team will remember isn’t the logo on the notebook—it’s how they felt. Cared for, connected, and seen. Use nature. Use movement. Use music. But most of all, use heart.
Balance strategic sessions with creative challenges and lighthearted bonding. One of our favorite formats is a “wisdom walk” with reflection prompts. Another? Ropes courses and group art builds.
This is where the insights land. After any activity, ask: What happened? What did we learn? What’s transferable to our work? Without this reflection, much of the value gets lost.
Start by acknowledging what people gave up to be here—time with family, stress of travel—and thank them. End by capturing takeaways, action steps, and moments of appreciation. That’s what makes it stick
Whether you’re working with a shoestring budget or flying your team to Colorado, the key is: create an experience. One that reflects your people and your purpose. And one that sparks something new.
Need support designing a retreat that works? Explore our podcast and planning resources, or reach out for customized help.
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Christine Courtney is a leadership educator, facilitator, and podcast host helping leaders build emotionally intelligent, people-first workplaces.