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10 Tips to Avoid Hiring a Dud Strategic Planning Facilitator

Updated: Apr 24

best strategic planning facilitator
Sometimes You Get What You Pay For!

Out for Charlatans!

Avoid Hiring a Dud Strategic Planning Facilitator


Hosting a strategic planning session can be costly and time-consuming. You can spend hours and hours trying to find a suitable venue, hire caterers, organize pre-work, and wrangle all the attendees. But often times, the biggest cost is the one you spend on hiring the facilitator.


Then, the big day arrives. Everyone is prepared and excited to roll up their sleeves, grapple with pressing issues, and create a roadmap for the future. They have high expectations the day will be a huge success and that the facilitator will be outstanding.


But when the day turns out to be a huge belly flop because the facilitator was a huge dud that wasted everyone’s time and the organization’s money, it can make the organization be wary of ever hiring another facilitator.


Therefore, when hiring a strategic planning facilitator, it's crucial to be cautious and thorough to avoid falling victim to ineffective facilitators who overpromise and underdeliver. Here are ten things to look out for the next time you’re scouting for a facilitator:


1. Credentials and Experience

Ensure the facilitator has relevant credentials and a proven track record in strategic planning facilitation. How many years did they work in the industry? What was their role? Why did they leave the industry to become a facilitator? Have they won awards or received accolades? Did they get their credentials online? Look for a facilitator whose credentials and experience greatly impress and wow you.


They should be able to offer valuable insights and guidance based on their years, if not decades, of expertise within the field. This wisdom can prove to be invaluable to keep the process moving when people attending a planning session hit a snag, feel lost, and aren’t sure what would be course of action or direction should be taken.


2. Look for References and Testimonials

Ask for references from their last three clients (so they can’t cherry pick their favorites) and then call the references to gauge their satisfaction with the facilitator's services. Ask poignant questions: Did the facilitator “knock it out of the park?” Did they exceed expectations? Was the day high impact? Would you hire them again? Were they dynamic, fun, and engaging?


Testimonials and case studies can also provide insights into a facilitator's effectiveness. The facilitator’s website should have many written testimonials—and even better, video testimonials. The best strategic planning facilitators have raving endorsements from senior executives and board members, and proudly showcase them.


3. Transparent Pricing

Be wary of facilitators who are not transparent about their pricing or who have vague or hidden fees. A reputable facilitator should provide a detailed breakdown of costs and deliverables, and happily write up a formal agreement. They will also provide a scaled fee structure based on an organization’s budget size, number of attendees, and number of days.


4. Customized Approach

Avoid facilitators who offer one-size-fits-all solutions or refuse to adapt their approach to meet your organization's specific needs and goals. A good facilitator should tailor their methodology to suit your unique circumstances and build a “custom” planning session. A canned approach is a red flag and should send you running to pursue other facilitators.


5. Clear Process and Timeline

Ensure the facilitator outlines a clear process and timeline for the strategic planning process. The best strategic planning facilitators usually require detailed pre-work, will review various documents, conduct interviews, create a planning session workbook, offer post-session implantation and execution tools, and provide follow-up calls. Beware of vague or overly optimistic promises regarding outcomes and timeframes.


6. Communication Skills

During the exploratory phase of the hiring process, pay attention to the facilitator's communication style and ability to listen attentively to your organization's concerns and objectives. Effective communication is essential for successful strategic planning. When talking with the facilitator, do they ask thought-provoking questions? Do they listen more than they talk? Do they sound like they genuinely care? Did they do research about your organization before your first call? Did they sound professional, positive, and easy-going?


7. Conflict Resolution Skills

Strategic planning sessions may involve conflicting viewpoints or tensions within the organization. A skilled facilitator should be adept at managing conflicts constructively and fostering collaboration. An effective way to vet this is to ask the facilitator what their process is when dealing with a conflict. Also, when you talk with references, ask how the facilitator handled any conflicts that came up at the planning session, or how they feel the facilitator would manage conflict and tensions if they came up.


8. Commitment to Follow-Up and Support

Ensure the facilitator is committed to providing ongoing support beyond the initial planning sessions. Follow-up assistance with implementation, execution, and evaluation can significantly enhance the success of the strategic planning process. Many times, this is an add-on cost, but if the facilitator was exceptional, it can be well worth it.


9. Trust Your Instincts

Ultimately, trust your instincts when evaluating potential facilitators. If something feels off or if the facilitator's approach seems too good to be true, or they don’t have clear fees, or they don’t offer post-session support, it's better to err on the side of caution and explore other options.

10. Don’t Get Stuck Thinking “Local”

Sure, it’s nice to hire local, but sometimes going with a local facilitator means mediocre results. Your strategic planning session is too important to skimp on. And though you may feel it’s risky and will cost more to hire a facilitator from outside your region, it may also be a game-changer. They can have more knowledge and experience, provide non-local perspective and objectivity, and their fees may be comparable, if not less expensive. So, explore facilitators outside your region; you just may find a gem at a price you can afford.



By paying attention to these key factors and conducting thorough due diligence, you can mitigate the risk of hiring a shoddy facilitator. The best strategic planning facilitators may cost more, but often times you get what you pay for so be willing to look outside your region. And in some cases, their insights and wisdom will be worth many times what you paid them.


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Tom's Books and Channels

Tom Iselin has built four sector-leading nonprofits and four foundations. He’s written six books, sits on three 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 and most popular 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.

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