How to Find and Hire the Best Strategic Planning Facilitator – a 9-Point Checklist
- Tom Iselin
- Jun 25, 2023
- 5 min read
Updated: Dec 17, 2025
Screening for the Best Strategic Planning Facilitators
Have you ever sat through a strategic planning session where you spent most of the day watching the clock, daydreaming, or checking your phone?
Did the facilitator burn hours wordsmithing your mission statement or running a tired SWOT analysis? Were they unengaging? Did the day fall far short of expectations? Did the resulting plan get filed away—never to be seen again? Did the “outcomes” quickly grow stale and have little real impact on your organization?
If you answered yes to any of these questions, it’s time to find a new facilitator.
But how do you choose the right one?
Below is a practical checklist you can use when scouting for the best strategic planning facilitator—one who delivers clarity, momentum, and results.
In-the-Trenches Experience
Be careful here.
More than 60 percent of nonprofit strategic planning facilitators have never actually run a nonprofit. Many earned credentials through shallow online courses and now call themselves experts.
The best facilitators have started, led, or run multiple nonprofits. They’ve raised money. They’ve dealt with difficult boards. They’ve managed growth, failure, and recovery.
Because they’ve been where you are, they can:
Empathize with your challenges
Offer real-world solutions
Draw on hard-earned successes and mistakes
Experience matters—especially when things get messy.
Credibility You Can Verify
Great facilitators leave a trail.
They have:
Numerous written and video testimonials
Long client lists
Strong references
Books, blogs, or podcasts that demonstrate thought leadership
When you ask for references, they don’t cherry-pick their “best three.” They confidently offer their most recent three.
If a facilitator’s website looks like a messy kitchen, lists only a few testimonials—or none at all—run.
Results-Driven, Not Process-Driven
You’re paying good money. You should expect exceptional service and measurable outcomes.
The best facilitators are as invested in your success as you are. They consistently go above and beyond and exceed expectations.
At the end of the process, your board and staff should feel:
Energized
Unified
Focused
Most importantly, you should walk away with a clear roadmap, defined priorities, and strategic direction that moves your organization to the next level of performance and impact.
Avoids Old-School Time Wasters
If a facilitator spends half the day asking basic questions about your organization, running SWOT analyses, or wordsmithing mission statements, that’s a red flag.
The best facilitators handle these tasks before the retreat through:
Pre-retreat surveys
Interviews
Data review
Written exercises
This frees up valuable in-person time for what actually matters: strategy, decision-making, and alignment.
Inspirational and Exceptional Communicator
No one wants to listen to a monotone facilitator hiding behind a lectern and reading dull PowerPoint slides.
The best facilitators are:
High-energy and engaging
Clear and practical
Excellent storytellers
Comfortable motivating a room
They also design sessions that are fun, meaningful, and memorable—often incorporating team-building activities to strengthen relationships and break up the day.
Facilitates with Confidence and Control
Strategic planning should never be hijacked by dominant personalities.
The best facilitators confidently guide the process and know how to:
Manage strong voices
Control derailments
Handle conflict productively
Ensure everyone is heard
Build consensus and buy-in
Expect movement, interaction, and small-group work—not eight hours of sitting and listening.
Asks the Right Questions at the Right Time
Anyone can ask standard questions and produce a generic plan.
What separates average facilitators from exceptional ones is their ability to ask the right question at the right moment—the kind that unlocks insight, clarity, and momentum.
They don’t follow scripts.They read the room.They adapt in real time.
This is hard to assess in an interview, which is why testimonials and references matter so much.
Strategic planning at this level is an art—and the best facilitators are master conductors.
Uses a Comprehensive Assessment Process
Great facilitators do serious homework.
Before the retreat, they gather and analyze information through:
Online surveys
Fundraising and financial metrics
Marketing and communications review
Culture assessments
Program and operational analysis
Stakeholder and beneficiary feedback
They speak directly with board members and staff to understand what’s really happening.
If a facilitator lacks a comprehensive assessment process, keep looking.
Provides Accountability and Management Tools
A strategic plan that sits in a file is worthless.
The best facilitators ensure implementation by providing:
A clear execution plan
Defined ownership
Accountability systems
Ongoing support or follow-up
They also offer a custom management tool or dashboard to track progress—not a clunky Word document crammed into a few columns.
Execution is where strategy succeeds or fails.
Takeaways
If you want a strategic planning process that actually works:
Prioritize real nonprofit experience
Demand credibility and proof
Insist on outcomes, not just discussion
Avoid outdated facilitation tactics
Choose someone who controls the room and drives execution
The right facilitator doesn’t just guide a conversation—they move your organization forward.
Summary
Strategic planning is too important—and too expensive—to waste on the wrong facilitator.
Use this checklist to choose wisely. When you do, your planning session won’t be something people dread. It will be something they talk about—and act on—for months to come.
Tom Iselin
“America’s Best Board Retreat and Strategic Planning Facilitator”
Additional Resources:
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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:
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