Podcast: Board Retreat and Strategic Planning Facilitators: How to Search Out the Best!
- Tom Iselin
- Oct 20, 2023
- 3 min read
Updated: Dec 17, 2025
How to Search Out the Best
Board Retreat and Strategic Planning Facilitators:
Listen in as Tom walks through a 9-point checklist of essential attributes you can use when scouting for the best board retreat or strategic planning facilitator.
Board retreats and strategic planning sessions represent significant investments. They require money, energy, and preparation—but most importantly, they require people’s time.
And nothing kills enthusiasm faster than feeling like that time was wasted.
Why So Many Retreats Fall Flat
Board members and staff often dread retreats for one simple reason: too many of them deliver very little value.
When retreats are poorly facilitated, people experience:
Long days with little direction
Generic content that doesn’t apply
Endless discussion without outcomes
No follow-through after the session
Wasting the time of board members and staff is the number one reason people come to resent retreats and planning sessions.
Why the Facilitator Makes All the Difference
The difference between a forgettable retreat and a high-impact experience usually comes down to one factor: the facilitator.
The best facilitators:
Create high value and high impact
Keep people engaged and energized
Design sessions that lead to clear outcomes
Make the day productive and enjoyable
Deliver results at a price nonprofits can afford
Great facilitators don’t just manage conversations—they drive clarity, alignment, and momentum.
What to Look for in a Top-Tier Facilitator
In the podcast, Tom breaks down a practical 9-point checklist to help you evaluate facilitators before you hire them.
You’ll learn how to:
Spot facilitators who truly understand nonprofits
Avoid flashy presenters with little substance
Ask the right questions during the selection process
Identify facilitators who focus on outcomes, not talk
Choose someone who fits your culture and budget
Takeaways
If you want a retreat that people actually appreciate and talk about afterward:
Prioritize facilitation quality over convenience
Protect the time of your board and staff
Look for engagement, outcomes, and follow-through
Choose facilitators who understand nonprofit realities
The right facilitator transforms the entire experience.
Summary
Board retreats and strategic planning sessions should never feel like an obligation or a waste of time. When led by the right facilitator, they become powerful moments of clarity, alignment, and progress.
Listen to the podcast and let Tom guide you through the 9-point checklist you need to find that one-of-a-kind facilitator.
Because when you choose wisely, you don’t just get a good retreat—you get the best board retreat and strategic planning facilitation ever.
Additional Resources:
Related Article
Tom's Books, Podcasts, and YouTube Channel
About the Author
Tom Iselin is recognized as one of America’s leading authorities on high-performance nonprofits. He has built nine sector-leading nonprofits and two software companies, written six books, sits on multiple boards, and has been rated one of America’s Best Board Retreat and Strategic Planning Facilitators. His work on nonprofit strategy, board leadership, and culture has been featured on CNN, Nightline, and in Newsweek.
Tom is the president of First Things First, a firm specializing in board retreats, strategic planning services, fundraising strategy, and executive coaching for nonprofit CEOs.
Board Retreats & Strategic Planning
If you’re looking for a board retreat facilitator or strategic planning facilitator who has been in the trenches and understands real-world nonprofit challenges, Tom can help your board gain clarity, build alignment, and create an actionable plan that improves performance and impact. His sessions propel organizations to the next level of performance and impact . . . and they're fun!
Board Retreats and Strategic Planning Services:
858.888.2278
