How to Plan a Leadership Workshop That Leaves a Lasting Impact
If your team is meeting—but not growing—it may be time for a different approach. A leadership workshop in a peaceful, curated space creates room not just for ideas—but transformation. In this post, we’ll walk you through exactly how to design an experience that fosters insight, unity, and real momentum—and why choosing the right setting makes all the difference. At Journey to The Well, we guide organizations in crafting leadership moments that carry well beyond the retreat weekend.
Define Clear Objectives
Begin by asking: What do you truly want this workshop to accomplish?
Strengthen leadership alignment?
Boost team communication and trust?
Build actionable strategy for the year ahead?
Your goal needs to be crystal clear—so all elements, from teaching sessions to location, support it.
Structure the Experience Around Purpose
Morning teaching + midday reflection time—to process messages and let ideas sink in.
Group breakout sessions or workshop projects—giving hands-on engagement.
Rest-focused evening/Q&A time—to build trust and deeper conversations.
This intentional rhythm helps learning resonate, not just inform.
Why Venue Choice Is a Game-Changer
Holding a leadership workshop at Journey to The Well means you get more than meeting rooms:
Shared spaces for discussion or quiet reflection between sessions
Six cozy houses and central lodge designed for group flow
Access to trails, firepit evenings, kayaking, golf-cart transport—natural spaces that deepen connection
It’s more than a hotel conference room — it’s about creating family in the workplace, and the space you choose drives the feelings you evoke.
View Our Campus
hear it from our guests
“As a recent guest at The Well, I can only give it my highest recommendation. The accommodations, the menu, and the staff are all beyond first rate. For a private getaway or group retreat, you will not find a better atmosphere or location. Five ENTHUSIASTIC stars!”
Andy Stanley - NYT Bestselling Author & Speaker
Final Details That Matter
When planning your leadership workshop:
Confirm your headcount (due 30 days ahead) so we can set up houses and meals efficiently.
Determine AV needs and meeting room setup in advance.
Ask about available meal and lifestyle accommodations (e.g., gluten-free, or early rise schedules).
Consider seasonality (indoor vs outdoor activities both local and on-site; ask us for recommendations)!
When leadership meets rest, real transformation happens. If you’re planning a leadership workshop or team development retreat, consider what environment you’re choosing for growth.
At Journey to The Well, we partner with leaders to design retreats that speak clearly—to both mind and soul.
