The Executive’s Excellence Checklist for Strategic Retreats
Critical Factors for Measurable Return on Your Next Leadership Gathering
Retreats aren't just agenda-filling—they can drive belonging, alignment, and business impact that lasts. This checklist gives you every critical factor the top teams use to ensure their offsite is unforgettable and valuable.
Section 1. The Excellence Checklist
Circle “Yes” “No” or “Needs Work” for each:
Retreat starts with a clear purpose—not just a list of topics
Yes No Needs Work
Every key stakeholder is involved in agenda-building
Yes No Needs Work
Agenda allows for both structured work and open, informal connections
Yes No Needs Work
There is dedicated time for candid, even tough, conversations
Yes No Needs Work
The offsite environment supports privacy, focus, and inspiration
Yes No Needs Work
Measures of success (“how will we know this worked?”) are set before arrival
Yes No Needs Work
A plan is in place for capturing outcomes, actions, and new ideas in real time
Yes No Needs Work
Leadership demonstrates vulnerability and models participation
Yes No Needs Work
Space for feedback—mid-retreat AND after—is built in
Yes No Needs Work
There is a follow-up process/local champion to ensure commitments don’t disappear
Yes No Needs Work
Bonus Section
“Red Flag Triggers”:
Signs a retreat will underperform (“VP skipped the discussion,” “Agenda = back-to-back PowerPoints,” “no one assigned for post-event action items”)
Example: "If you check fewer than 7 boxes, revisit your planning process!"
Section 2. Pro Tips for Maximum ROI
Align pre-event surveys or 1:1 interviews
Co-design a legacy moment: something memorable unique to your team and this retreat
Use the setting for team wellness or “energy up” breaks, not just work
Want a free pre-event consult or a custom version for your team? Let us help your retreat exceed every expectation.
Book a complimentary Retreat Impact Consult with our Flying Horse Experience Team. Meet@FlyingHorseClub.com or (719) 487-2662