Board Development Facilitator - Find the IDEAL Facilitator
- Tom Iselin
- May 29, 2021
- 3 min read
Updated: 2 days ago
Board Development Facilitator
Find the IDEAL Facilitator
What to Look For
Ever walked into a board retreat hoping for clarity and inspiration… and instead found yourself silently begging for the lunch break to arrive? Maybe the facilitator droned through slides, spent half the morning wordsmithing statements no one cared about, or delivered content that felt stale, generic, and disconnected from reality.
If the retreat ended with yawns, blank stares, and notes that never saw daylight again, you’re not alone — and it’s absolutely time for an upgrade.
Below is a refreshed set of qualities to look for when evaluating who should lead your next board development retreat — rewritten so it stands apart from your other articles.
Real Leadership Experience
A surprising majority of “board development or retreat facilitators” have never actually led a nonprofit. That gap matters. The strongest facilitators are people who have started organizations, managed boards, raised money, and lived the pressure you’re under. Their experience gives them the ability to relate, to understand board dysfunction, and to offer real-world solutions grounded in practice—not theory.
Reputation You Can Verify
Quality leaves a trail. Top-notch facilitators showcase a wide range of client testimonials, video reviews, reference lists, and evidence of thought leadership such as articles, guides, or books. If a facilitator’s website is sparse, outdated, or has only a couple of lukewarm reviews, that’s your sign to move on.
Focused on Impact, Not Fluff
A board retreat should leave people energized, aligned, and ready to show up differently. That takes a facilitator who is deeply committed to elevating your board—not just entertaining them. Look for someone who consistently produces clear outcomes, practical next steps, and a renewed sense of purpose among board members.
Confident, Skilled Group Leadership
Strong personalities can hijack a retreat if they’re not managed well. Great facilitators know how to structure conversations, redirect repetitive voices, elevate quieter members, and keep discussions productive. They guide the room with assurance, fairness, and creativity — and they make sure the day belongs to everyone, not just the loudest person.
Creates an Enjoyable Experience
Board retreats don’t have to feel like dental work. The best facilitators make the day lively and interactive. They integrate exercises that spark laughter, connection, and teamwork. They use humor, movement, and memorable moments to keep people engaged — because a board that’s awake learns better, collaborates better, and commits better.
High-Energy, Clear Communicator
A great facilitator brings enthusiasm and presence. They know how to motivate a room, tell a compelling story, and communicate complex ideas in a way that feels simple and actionable. They’re engaging without being cheesy, inspiring without being dramatic, and clear without being condescending.
Masterful Question-Asking
What separates an average facilitator from a transformative one? Their questions. Exceptional facilitators ask questions that reveal blind spots, challenge assumptions, and lead boards to powerful insights. They don’t rely on templates. They listen, pivot, dig deeper, and guide the group toward meaningful realizations.
Thorough Pre-Retreat Preparation
The retreat doesn’t start in the room — it starts weeks before. Strong facilitators gather input through surveys, interviews, culture assessments, and organizational reviews. They arrive with a deep understanding of your board’s strengths, limitations, and history. If someone shows up unprepared or without a defined pre-retreat process, keep looking.
Provides Tools for Follow-Through
A retreat is only as good as what happens afterward. The best facilitators don’t hand you a stack of notes and disappear. They provide implementation frameworks, accountability processes, and user-friendly tools that help your board track progress. No cluttered spreadsheets or clunky Word docs — just clean, functional systems that keep momentum alive.
Tom Iselin
Rated One of America’s Best Board Retreat
and Strategic Planning Facilitators
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
