Is Your Leadership Retreat Designed for Impact or Activity?
A Purpose-Driven Self-Assessment for Executive Corporate Retreats
Welcome!
How confident are you that your next corporate retreat will do more than check a box? The world’s top teams raise the bar on connection, clarity, and legacy—not just “time away.”
This 10-minute self-assessment reveals if your retreat plan will truly move your people, shape real culture, and deliver business value for your leaders and organization.
Quick Start: Instructions
For each question, rate your answer from 1 (Never) to 5 (Always).
At the end, tally your score and get personalized recommendations.
Best used as a team with leadership, People Ops, or your event/HR planner.
With respect,
The Flying Horse Strategic Retreat Team
Section 1. The Real Retreat Readiness Test
Section 2. Results & Reflection
Score Yourself:
48–60: Your retreat is primed for legacy and impact. Spread this discipline across your org!
36–47: Good foundational planning—but add 2–3 “level up” moments for an unforgettable retreat.
24–35: You risk a “nice event, little impact” outcome. Prioritize ownership, connection, and follow-through.
Below 24: High danger of wasted investment, disengaged execs, or “another year, another retreat.” Time for serious change.
Section 3. Retreat Planning Gaps – What To Watch For
Look at where you scored 3 or lower.
Are you missing real dialogue time?
Do execs truly *own* the design, or is this HR’s project?
Are next steps always clear, and is feedback actively sought?
Is the experience adaptable, or is it “set-it-and-forget-it”?
Remember: Logistics matter, but connection and legacy are the true ROI for any leadership retreat.
Section 4. Three Fast Fixes For A Standout Retreat
1. Start with Legacy: In your next team call, ask, “How do we want people to describe this retreat a year from now?”
2. Plan for Genuine Dialogue: Schedule at least 20% of retreat time for discussion, reflection, and unstructured team moments.
3. Assign Champions: Make every exec one “champion” area—wellness, candor, team story, fun, follow-up.
Bonus: Your Custom Action Plan
Prompt your team:
“What’s one change that would make this retreat a true inflection point for our culture?”
“Who outside the C-Suite should be part of at least one major session?”
“How will we ensure the ‘retreat effect’ endures for the next 90 days?”
Section 5. Ready To Transform Your Retreat?
If your retreat scores below expectations, or you’re hungry for breakthrough—not just “boxchecking”— Flying Horse’s experts will help you design the ideal agenda and environment for legacy, culture, and results.
Brought to you by the “Belonging & Connection” retreat experts at Flying Horse Resort & Club. We help leadership teams craft experiences that drive trust, energy, and future performance. Meet@FlyingHorseClub.com or (719) 487-2662