Swiping Right: How to Choose the Right Facilitator

Photo Credit: Unsplash/Philip Oroni

Part 2 of 6 in the series “Not Every Facilitation Is a Love Story.”

In our last post, Tara made the case that hiring a facilitator is a lot like dating. You’re not looking for the most impressive profile. You’re looking for the right fit. She also pointed out that much of the damage from a bad match happens before anyone is hired.

I’d push that even earlier. In my experience, many bad matches are made before anyone starts scrolling. So the first step in finding a good match isn’t searching at all.

Know what you're looking for before you start swiping

The single biggest mistake I see is shopping for a facilitator before you can name the problem. "We need a strategic plan" isn't a problem statement. Neither is "our board needs to get on the same page." Those are outcomes, and fuzzy ones at that.

Before you contact anyone, try finishing this sentence: We need to bring [these people] together to [make this decision / resolve this tension / build this thing], and right now we're stuck because [the real reason].

That last part is where the match gets made. Here’s how that sentence plays out in the three situations Tara introduced in Post 1:

• It's Complicated. Your association board and foundation board have years of history and very little trust. You're stuck because nobody believes the other side is acting in good faith. You need someone who is skilled at surfacing conflict safely, not just someone who runs a tidy agenda.
• The Comfortable Long-Term Match. You're due for a routine strategic plan refresh. You're stuck mostly because staff and volunteers are busy. You need a solid process and someone who can keep energy up. The real risk here isn't picking the wrong person; it's picking a generic one.
• The Whirlwind Romance. Your CEO resigned unexpectedly and the board meets in ten days. You're stuck because emotions are high and information is incomplete. You need someone who builds trust fast and keeps a rattled group from making a reactive decision.

Same word (facilitator), but three very different job descriptions.

How executives actually vet facilitators

Here’s the kind of thing we hear from association CEOs and executive directors about how they make this call.

"I almost never start with a Google search. My first call is to two or three peer CEOs who've been through something similar. I'm not asking, 'Who's good?' I'm asking, 'Who was good for that?' Those are very different questions." 

"The discovery call tells me everything. The facilitator we ultimately hired spent 45 minutes asking about our history and our board dynamics before she said a single word about her process. The one we passed on had a slide deck ready before I finished describing the problem." 

"Years ago, we hired a big-name firm for a board retreat and got a junior associate we'd never met. Lovely person, wrong room. Now the first thing I ask is, 'Who exactly will be standing in front of my board?' and I want to talk to that person before we sign anything." 

What credentials should (and shouldn't) tell you

I'll be honest: I'm a credentials person. I'm a certified Technology of Participation (ToP) facilitator and mentor trainer. Credentials tell you someone has learned a method, been assessed against a standard, and likely belongs to a community of practice.

What credentials don't tell you is whether that person can read your room. A certification says someone knows how to run a process. It doesn't say whether they'll notice that your board chair and your treasurer haven't made eye contact in two years. Treat credentials as a floor, not a finish line.

Industry experience is another résumé item worth putting in perspective. As Tara noted in Post 1, your board already brings the subject-matter expertise. What it needs is someone who can help put that expertise to use, so treat industry familiarity as a bonus, not a requirement.

Check for chemistry, not just the résumé

You wouldn't marry someone based on their profile alone. Here's how to get past the bio:

• Have a real discovery conversation. Not a sales pitch, a conversation. Pay attention to the ratio. A good facilitator spends most of that call asking questions and listening.
• Make the reference calls. And ask better questions than, "Were you happy?" Try: What surprised you? What did they do when the room got tense? What would you do differently if you hired them again?
• Ask to see them in action. A recorded session, a sample agenda, a short demo, or a webinar they've led. You're looking for how they hold space, not how they present.

Questions to ask before you commit

Once you’ve narrowed your list, these questions can show you how a candidate thinks, not just what they’ve done:

• Walk me through how you'd design a session for our situation. What would you need to know first?
• Tell me about a session that went sideways. What did you do?
• Who, specifically, will be in the room facilitating?
• How do you handle a participant who dominates, or one who checks out?
• What happens after the session? What will we walk away with, and when?

Questions they should be asking you

A strong facilitator will interview you right back. Listen for questions like these:

• What's the history behind this? What's been tried before?
• Who are the key personalities, and where do people tend to disagree?
• What decisions are actually on the table, and what's already been decided?
• Who has the authority to act on what comes out of this session?
• What does success look like to you, and to your board chair?

If a candidate doesn't ask about history, politics, and decision rights, they're likely planning to run their standard playbook. That might be fine for the Comfortable Long-Term Match. It's a real problem, though, for It's Complicated.

Give them what they need to succeed

The best match in the world can't succeed without context. Once you're getting serious with a candidate, be forthcoming. Start with your goals: what you need this engagement to produce, and what you'll do with it afterward. Then share the governing documents, the last strategic plan, recent survey data, and, yes, the politics. A facilitator who walks into an It's Complicated situation without knowing the backstory is set up to fail, no matter how talented they are.

In a Whirlwind Romance, you may have little to share. Say what you know, what you don't, and what worries you.

Red flags, even at the swiping stage

Tara will dig into these in Post 5, but a few warning signs show up early:

• They pitch a solution before they understand your problem.
• Every example they share sounds identical, regardless of the situation.
• They can't describe what you'll receive afterward, or when.

The bottom line

Swiping right should follow a few good conversations, not a polished website. Know your problem, look past the profile, and notice the questions they ask you. That's where fit shows up.

Next up: Tara takes on "Meeting the Parents," how to sell the match to your board and get everyone dating the same person.

---

Aaron Wolowiec, FASAE, CAE, CMP Fellow, is founder and president of Event Garde and a certified Technology of Participation (ToP) facilitator and mentor trainer who helps associations think collaboratively, plan more boldly, and implement with intention.