For the Best Strategic Planning Facilitators, Look Beyond Your City Limits
- Tom Iselin
- Oct 20, 2023
- 3 min read
Updated: Dec 17, 2025
For the Best Strategic Planning Facilitators,
Look Beyond Your City Limits
Listen to this podcast and learn several important reasons why you should consider looking beyond your city limits when searching for your next board retreat or strategic planning facilitator.
Hiring locally often feels like the safest option. Familiar. Convenient. Comfortable. But when it comes to board retreats and strategic planning sessions, staying local can unintentionally limit your options—and your outcomes.
Why Board Retreats and Strategic Planning Sessions Matter
One of the most effective ways to strengthen your board and nonprofit organization is by hosting a well-designed board retreat or strategic planning session.
When done well, these sessions can:
Improve board engagement and performance
Strengthen governance and leadership
Sharpen fundraising focus and effectiveness
Build alignment and trust
Create a clear roadmap for future impact
Because these days shape culture and direction, they deserve serious thought and intentional planning.
Why Hiring the Best Facilitator Matters More Than Hiring Local
Given the importance of these sessions, it’s critical to hire the best board retreat and strategic planning facilitator you can find—at a price you can afford.
Yes, hiring a facilitator from outside your region can feel risky. There’s travel. There’s unfamiliarity. There’s the unknown.
But expanding your search can also open the door to:
More experienced facilitators
Specialized nonprofit expertise
Proven retreat frameworks and processes
Fresh perspectives
Competitive or even lower pricing
Many highly qualified facilitators regularly work nationally and will often match the fees of local providers.
The Myth of “Local Is Always Better”
We all value supporting local businesses. Buying local produce. Hiring local contractors. Strengthening our communities.
But sometimes, you truly get what you pay for.
When it comes to board retreats and strategic planning sessions, hiring solely based on geography can result in:
Generic facilitation
Limited experience
Lackluster outcomes
Missed opportunities for growth
Facilitation is not a commodity. It’s a craft.
Board Retreat Facilitation Is an Art
High-quality board retreat and strategic planning facilitation is an art form. It requires experience, intuition, preparation, and the ability to guide complex conversations toward real outcomes.
Your retreat or planning session is far too important to treat as an experiment or a convenience hire.
The right facilitator—regardless of where they live—can elevate the entire experience and deliver measurable value.
Takeaways
Before defaulting to a local facilitator:
Expand your search beyond your region
Compare experience, not just proximity
Interview facilitators nationally
Focus on outcomes, not convenience
Protect the time and investment of your board
You may be surprised by what you find.
Summary
Board retreats and strategic planning sessions are pivotal moments for nonprofit organizations. They shape culture, clarify direction, and influence long-term impact.
Before making a final decision, take the time to thoughtfully search and interview facilitators outside your region. The best fit may not be local—but they may be more experienced, more effective, and even more affordable.
Listen to the podcast and discover why looking beyond your city just might lead to your best retreat yet.
Tom Iselin
“One of America’s Best Board Retreat and
Strategic Planning Facilitators”
Additional Resources:
Articles
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
