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How to Find and Hire the Best Strategic Planning Facilitator – a 9-Point Checklist . . .

Screening for the Best Strategic Planning Facilitators


Have you ever sat through a strategic planning session and spent most of the time watching the clock, daydreaming, and checking texts? Did the facilitator waste most of the day wordsmithing your mission statement and conducting SWOT analysis? Were they unengaging? Did the sessions that fall far short of your expectations? Did the resulting plan collect dust in a file because it was never seen again? Did the outcomes of the day grow stale and ultimately have little 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? What follows is a checklist of attributes you can use when scouting for the “best” strategic planning facilitator.

1. In-the-Trenches Experience

Watch out! More than 60 percent of nonprofit strategic planning facilitators have never run a nonprofit. Many, and I mean many, planning “facilitators” are charlatans who got their credentials taking hokey online courses. The best facilitators have started or run multiple nonprofits. They can empathize with where you are because they’ve been where you are. They know firsthand the hardships of raising money, working with unruly board members, and managing expansion. And they provide insights on key issues that can prove invaluable because they can draw from the successes and perils of their in-the-trenches experience.

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. If you ask for references, they won’t provide their best three, they provide their last three. They often have their own 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 clients, or worse yet, none of each . . . run!

3. Results-Driven

It’s fair to expect exceptional service and specific outcomes from a facilitator. And why not . . . you’re paying good money! You want to hire a facilitator who is as passionate about your success as you and your team are. Look for someone with a record of going above and beyond, and exceeding expectations (watch video testimonials and call references). In the end, your board and staff should feel refreshed, inspired, and unified. Most importantly, you should leave with a clearly defined roadmap of priorities and a direction that will take your organization to the next level of performance and impact so your mission can soar!

4. Avoids Old-School Tactics

If you’ve sat through a strategic planning session where the facilitator wasted hours asking basic questions about your organization, conducting SWOT analysis, or wordsmithing a mission statement, you know what a HUGE waste of time it is. The best facilitators use pre-retreat exercises that manage time-consuming processes like these. This means more time—much more—can be spent during the planning session to discuss strategy and the big issues at hand.

5. 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, motivating, a master storyteller, and uses tactics to make the process fun, meaningful, and memorable. They will also incorporate team-building exercises to break up the day with some laughs and build relationships.

6. Facilitates and Engages with Confidence

We’ve all taken part in strategic planning sessions where the day was steamrolled by strong personalities. It’s maddening! Strategic planning should be a democratic process, not an autocracy. The best facilitators will confidently take you on a journey of exploration, education, discussion, and action 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.

7. Asks the Right Questions

Anyone can ask standard questions that will lead to a set of priorities, goals, objectives, and action plans. 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. Assessing this trait is difficult when inter­viewing facilitators, but you can glean insights from former clients, which is why you want to watch testi­monial videos and call references. Orchestrating a productive, fun, and high-impact strategic planning process is an art and the best facilitators are master artists (conductors).

8. Uses a Comprehensive Assessment Process

The best facilitators spend a lot time collecting information before the planning session. They use online surveys, analyze fundraising metrics, review marketing collateral, assess culture, and review key indicators from every functional area of an organization. They will make calls to select board members and staff, and solicit feedback from stakeholders and beneficiaries. If a facilitator lacks a comprehensive process for collecting, analyzing, and presenting key information about an organization, move on to the next candidate.

9. Offers Accountability and Management Tools

Why spend a bunch of money for a roadmap of success if it sits in a file and collects dust? The best strategic planning facilitators provide an implementation plan and on-going support services. This includes an accountability process to ensure the people overseeing the execution of the plan get things done on time. Facilitators should also provide a custom management tool (dashboard) to manage the details of the action plans . . . and make sure it’s not some cheesy Word document that squishes all the actions plans into a few columns.

Tom Iselin

“America’s Best Board Retreat and Strategic Planning Facilitator”

Additional Resources:


Finding the Best Strategic Planning Facilitator – 7 Things to Look For

Find the Best Board Develop Facilitator and Trainer - 9 Things to Look For

Best Board Retreat and Strategic Planning Facilitation: Checklist for Hosting the Best Board Retreat and Strategic Planning Session Ever!

Tom's Books and Channels

Check out Tom's latest books on culture, nonprofit management, and fundraising

Tom's YouTube Channel: The Nonprofit Mentor

Tom's Podcast: The Fundraising Coach

Tom's Podcast: The Nonprofit Mentor

About First Things First

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 America's best board retreat and strategic planning facilitator and is 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:

Author: Tom Iselin

Best Board Retreats

First Things First Homepage


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