TLDR:
The best facilitators aren't the ones with perfect agendas—they're the ones who make people feel safe enough to tell the truth. In a recent workshop, someone sheepishly admitted "It starts when I email her..." This triggered a domino effect as the team revealed their "simple" website change actually ping-ponged through 7 different people. The room erupted in laughter—not at each other, but at the absurd system they'd all been quietly navigating.
Real leadership isn't about having answers, it's about creating permission for people to share what's actually happening. Whether you're running a boardroom meeting or connecting with your teenager, the skill is the same—staying curious instead of controlling, and becoming someone who's safe enough to be honest with. Being impressive is optional. Being trustworthy isn't.
Main Article
Facilitation isn’t about running meetings or managing time—it’s about creating spaces where people feel safe enough to tell the truth. Whether in a boardroom or a living room, the real work of leadership is making it safe to be honest, ask hard questions, and share what’s really going on. The room is the work.
I was in California this week, leading another workshop. Different zip code, different faces, same core work: equipping smart people to solve hard problems together.
And I’ve been thinking a lot about what it actually means to facilitate, not just run a meeting, but to command the room in a way that makes others feel safe enough to lead inside it.
Here’s what it’s not:
It’s not keeping time.
It’s not nudging people toward consensus.
It’s not whiteboarding ideas or building a deck that proves how clever we are.
The real job is quieter.
And harder.
My experience suggests that good facilitation means creating a space people actually trust with their hard questions. A space where they can tell the truth about what’s working, what’s not, and what’s keeping them up at night, without the quiet fear of looking dumb, slow, or not “strategic” enough.
That kind of space can’t be forced.
But I think it can be invited.
There was a moment in a recent workshop, perhaps my favorite kind of moment, when we were mapping out an internal process for a relatively straightforward website change.
Someone raised their hand and said, almost sheepishly, "It starts when I email her," nodding to someone else in the room. That one comment unlocked a chain reaction. The woman he emailed laughed and added, "Yeah, and I forwarded it to another person."
Then another person jumped in: "It came to me next."
More voices chimed in, each admitting they had tried to move the same request forward by emailing someone else, hoping it would eventually land with the right person. Eventually, it did. But only after ping-ponging across the organization 7 times.
The room cracked up.
Here’s what mattered: there was no blame in the air. No side glances or defensiveness. Just a group of high-performing adults laughing, not at each other, but at the absurdity of a system that was clearly broken.
That moment was a highlight for me.
Not because we solved the workflow with AI automation. (We didn’t. Not right away.)
But because people felt safe enough to share the truth out loud.
That’s the signal I look for now. Not performance, but permission.
I’ve been sitting with that since. And not just in a business context.
I’ve got three teenagers at home (and I genuinely love it). That means most of my parenting lately is not about telling them the “right” thing to do, it’s about creating the kind of relationship where they’d want to tell me what’s actually going on.
That’s harder than it sounds.
I don’t get a whiteboard.
There’s no agenda slide.
And my facilitation skills are not nearly as smooth when there’s dirty laundry on the stairs and one-word answers from the backseat.
But the work feels familiar.
Staying curious instead of controlling.
Asking better questions instead of rushing in with advice.
Creating the kind of space where they can tell the truth without worrying it’ll cost them embarrassment or a speech. And I tend to fail more in the living room than in the boardroom. But it's essentially the same job, just in a different room.
More and more, I think that’s what leadership really is.
Not just in meetings. Not just at home.
But in every room we care about.
To be the kind of person who can ask hard questions without trying to fix them right away.
To stay steady when the answers are messy.
To make it safe enough for people to say, “Here’s what’s really going on.”
I don’t have to be impressive.
I just have to be safe enough to be honest with.
And if I can keep practicing that—in work, in parenting, in life—then maybe I’m starting to understand what the real job is.