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How to Search Out and Find the Best Board Retreat and Strategic Planning Facilitator

Updated: Apr 24


Woman at mind mapping board at a Best Strategic Planning Session with Tom Iselin

Be Wise, Hire Smart!


Have you ever sat through a board development retreat and spent more time watching the clock, daydreaming, and checking texts than listening to the facilitator? Are your board members cringing at the thought of attending another retreat? Did your last facilitator stand behind a lectern and drone on like a record playing in slow motion? Did the outcomes of the day grow stale and ultimately have little impact on your board and your organization?


If you answered “yes” to any of these questions, it’s time to find a new facilitator/trainer -- and why not the Best Strategic Planning Facilitator!. But how do you choose? What follows is a checklist of attributes you can use when scouting for the “best” board development facilitator.

1. In-the-Trenches Experience

Watch out! More than 80 percent of board development facilitators have never started or run an organization. The best facilitators have started or run multiple businesses or nonprofits. They can empathize with where you are because they’ve been where you are.


They know firsthand the hardships of engaging board members, raising money, creating a unifying culture, and managing through the ups and downs of business cycles. And they can provide key insights that prove invaluable because they can draw from the successes and perils of their in-the-trenches experience. Therefore, hire someone who has been deep in the trenches multiple times.


2. Credibility

If a facilitator does good work, people will happily sing their praises. The best facilitators have dozens of written and video testimonials on their websites. They will have long lists of clients and references. They often have books, blogs, and podcasts. If you visit a prospective facilitator’s site and it looks like a messy kitchen and lists only a few testimonials, or worse yet, no testimonials . . . run!


3. Impact-Driven

It’s fair to expect exceptional service and high-impact outcomes from a facilitator. And why not . . . you’re paying good money! You want to hire a facilitator who is as passionate about improving the quality of your board and organization as you are. Look for someone with a record of going above and beyond, and exceeding expectations. In the end, your board should leave feeling inspired and unified. Most importantly, board members should leave feeling motivated to make the changes necessary that will take your board to the next level of performance and impact so your mission can soar!


4. Facilitates and Engages with Confidence

We’ve all taken part in board development retreats where the day was steamrolled by strong personalities, and it’s maddening. The best facilitators will confidently take you on a journey of exploration, education, discussion, and planning. Look for a facilitator who uses tactics to control hijackers, manage disputes, give everyone a voice, create buy-in, and build consensus. They will also have people up and moving around doing thoughtful, interactive exercises, usually in small groups to facilitate discussion and collaboration.


5. Makes the Day Fun!

Tired of squirming through board development retreats that fall short of your expectations? Did you get “rock butt” from sitting for hours, listening to the drone of nothingness!? Boring retreats provide no value and waste everyone’s time. The best facilitators make their retreats fun and lively, and they are quick witted and funny themselves. They incorporate engaging team-building exercises and icebreakers to break up the day with some laughs and to build relationships.


6. Enthusiastic, Inspirational, and Exceptional Communicator

No one wants to listen to a stoic facilitator pontificate behind a lectern reading lame PowerPoint slides. Yuck! The best facilitators are professional, intentional, and practical, but that doesn’t mean they are dull. Look for a facilitator who is enthusiastic, high-energy, motivational, a master storyteller, and uses retreat tactics to make the day fun, meaningful, and memorable.


7. Asks the Right Questions

Anyone can ask canned questions that lead to canned responses. What distinguishes the best facilitators from average ones is knowing the right questions to ask at the right moment to yield outstanding results. They don’t a follow a script. Ascertaining this is difficult when interviewing a facilitator, but you can glean insights from former clients, which is why you want to watch testimonial videos and call references. Facilitating a high-impact, memorable retreat is an art and the best facilitators are master artists.


8. Uses a Pre-Retreat Assessment Process

The best facilitators spend a lot time collecting information before the retreat. They use online surveys, analyze metrics, review marketing collateral, assess board culture, and review key information about an organization. They do their homework. They will make calls to select board members and staff, and solicit feedback from stakeholders if required. If a facilitator lacks a pre-retreat process for collecting, analyzing, and presenting key information about the board and organization, move on to the next candidate.


9. Offers High-Quality Accountability and Management Tools

Why spend a bunch of money on a retreat if the outcomes sit in a file and collect dust? The best board retreat facilitators provide an implementation plan and on-going support services. This includes an accountability process to ensure the people overseeing the execution of the outcomes get things done. Facilitators should also provide some type of management tool (dashboard) to manage retreat outcomes . . . and make sure it’s not some cheesy Word document that squishes all the actions plans into a few columns.


10. Look Beyond Local

Sure, it’s nice to support local vendors, but sometimes you get what you pay for . . . which can mean mediocre results. Retreats and planning sessions are too important to skimp on. Look beyond your region and state when searching. The good news is many facilitators adjust fees so they can compete with local facilitators. And most of the best facilitators adjust their fees based on the budget size of an organization, number of hours, and number of people attending the retreat. So, if you want to have a fun, memorable, and high-impact, retreat, search out the best, there’s no need to be pennywise and dollar foolish!


Additional Resources:


Toms Books and Channels:



Tom Iselin

“America’s Best Retreat and Strategic Planning Facilitator”



Tom Iselin has built four sector-leading nonprofits and four foundations. He’s written six books, sits on six boards, and hosts a video blog and podcast. Each year, Tom speaks to more than 5,000 nonprofit leaders at conferences across the country.


He is considered a leading authority on high-performance nonprofits, and his impact on the industry has been featured on CNN, Nightline, and in Newsweek.


Tom is the president of First Things First, a business specializing in board development retreats, strategic planning, fundraising, executive coaching, and speaking. To relax, he loves mountain biking, hiking, skiing, tennis, and baking.


If you’re in the hunt for the best board retreat/board development facilitation, or the best strategic planning facilitation, it would be a privilege to learn more about your organization and the aspirations you hope to achieve as you work to propel your noble mission. Jot me an email to set up a meet-and-greet call.


To learn more, visit:

858.888.2278

Looking for answers?

I’m here to help. Contact me . . .

TomIselin@gmail.com, or 858.888.2278




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