Find the Best Strategic Planner for Your Next Planning Session: 7 tips!
- Tom Iselin
- May 29, 2021
- 5 min read
Updated: Dec 11, 2025
Find the Best Strategic Planner for
Your Next Planning Session: 7 tips!
Have you ever sat through a strategic planning retreat watching the clock, sneaking looks at your phone, and wondering why you’re there? Maybe the facilitator burned half the day tweaking your mission statement and running a tired SWOT exercise. Maybe they were flat, unengaging, and the final “plan” disappeared into a folder and never saw daylight again.
If any of that sounds familiar, it’s time to hire someone new. But how do you sort the true pros from the pretenders? Use the checklist below to vet candidates and find a strategic planning facilitator who will actually move the needle for your organization.
Find the Best Strategic Planner . . . Here's How!
1. In-the-Trenches Experience
Be careful here. A shocking percentage of “strategic planning experts” have never led a nonprofit a single day in their lives.
You want someone who has:
Started or run multiple nonprofits
Dealt with dysfunctional boards, tight cash flow, and rapid growth
Wrestled with real-world challenges: fundraising, staffing, programs, culture
Facilitators with in-the-trenches experience bring more than theory. They can say, “I’ve been there,” and offer practical guidance drawn from wins, mistakes, and battle scars—not just a workbook.
2. Credibility You Can Verify (Don't skimp . . . Find the BEST strategic planner!)
A great planner doesn’t have to tell you they’re great—their body of work should. When you check them out online, look for signs of real, visible credibility:
Dozens of written and video testimonials
A solid, up-to-date client list
Books, articles, blogs, podcasts, or speaking engagements
A website that’s clear, organized, and easy to navigate
If their site looks like a cluttered closet, offers only vague claims, and shows little or no social proof? That’s a red flag. If other leaders aren’t raving about them, you probably won’t be either.
3. Obsessed with Outcomes (Not Just Activities)
You’re not hiring someone to “run a meeting.” You’re investing in better decisions, better alignment, and a better future for your organization.
Look for a facilitator who:
Talks about results—not just agendas and exercises
Has clients who can point to specific improvements after the retreat
Leaves organizations with a clear, practical roadmap of priorities and timelines
Helps boards and staff walk away energized, focused, and on the same page
By the end of the engagement, you should have a concise direction, a manageable set of priorities, and renewed confidence that your organization can reach the next level of performance and impact.
4. Uses Modern, Time-Smart Methods
Old-school strategic planning burns hours on things that could have been done before the retreat. If a facilitator spends half the day asking basic questions about your organization, wordsmithing your mission statement, or slogging through giant SWOT grids, you’re wasting precious time.
Top-tier planners:
Use pre-retreat surveys and interviews to gather core information
Push discovery work (history, baseline data, basic input) before everyone gets in the room
Design the session to focus on strategy, priorities, and tough decisions—not filler
You’re paying for strategic thinking, not for a live version of information they could have read in advance.
5. Inspiring and Clear Communicator
Nobody wants to spend the day listening to someone drone through PowerPoint slides and jargon.
A skilled strategic planning facilitator is:
Engaging, energetic, and easy to follow
A strong storyteller who uses real examples, not buzzwords
Practical—translating concepts into clear next steps
Intentional about making the day meaningful, memorable, and even fun
They’ll also weave in simple team-building activities to spark connection, break up the day, and build trust without turning the retreat into a game show.
6. Confident Facilitator, Not a Passive Moderator
If you’ve ever watched a planning session get hijacked by one or two strong personalities, you know how fast things can go sideways. Strategic planning should be inclusive—not dominated by the loudest voices.
The best planners:
Set expectations early and enforce them gently but firmly
Ensure quieter voices are heard
Manage conflict without letting it derail the day
Use tools and structures to keep the group on track and on time
Get people moving, talking, and working in small groups to spark thoughtful discussion
You want someone who can guide your board and staff through a structured journey of discovery, prioritization, and commitment—without letting sidebars and egos take over.
7. Asks Smart, Well-Timed Questions
Anyone can follow a script and ask generic questions that spit out goals and action items. That’s not what you’re looking for.
What sets a great facilitator apart is their ability to:
Ask the right question at the right moment
Go deeper when they sense confusion, fear, or avoidance
Reframe issues in ways that unlock new thinking
Shift direction when the conversation hits a wall
You won’t fully see this skill in a sales call, but you can look for clues. Watch testimonial videos and ask past clients what the facilitator was like “in the room.” The very best treat planning as an art form, not a checklist.
Bonus: Preparation and Follow-Through
Strong strategic planners don’t just show up and wing it. They put in serious prep time, which may include:
Online surveys for staff, board, and key stakeholders
Reviewing fundraising, program, financial, and marketing data
Assessing culture, engagement, and leadership dynamics
Holding pre-retreat calls with select board members and senior staff
And once the plan is created, they don’t disappear. Look for someone who offers:
A simple implementation framework and accountability process
Follow-up support or check-ins
A practical management tool or dashboard for tracking action items and progress
If the plan lives only in a binder or a Word document that nobody opens, you’ve wasted your money. The right facilitator will help you turn ideas into action—and action into impact.
Summary: What’s Next?
There’s no shortage of people calling themselves strategic planners. The real challenge is finding one who can help your organization think clearly, choose wisely, and execute consistently.
If you’re looking for a partner to lead your next planning effort and help you turn vision into reality, I’d be glad to learn more about your organization and the goals you’re driving toward. Send me an email and we’ll set up a brief meet-and-greet call to see if it’s a good fit.
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
