A few days ago, I found myself in the margins of a senior leadership offsite — one of those long-table affairs where no one’s quite sure whether to relax or hold their breath.
It was a “future of work” conversation, billed as strategic but simmering with unspoken tensions: AI, restructuring, legacy systems, job security. The big themes. The elephant in the room wasn’t so much a single issue as a stampede waiting for a signal.
About 40 minutes in, a leader paused mid-sentence, turned to me, and asked — a little too casually:
“So, in your experience… how do other organisations deal with this?”
And there it was. That subtle sidestep — the invitation to shift from “our uncomfortable reality” to “a neutral third-party example.” Not because they didn’t care, but because they weren’t ready to name it directly. Not yet.
This happens often in facilitation. The moment when people look outward — “What are others doing?” — not to compare, but to delay. To stall. To find a safe way back into their own discomfort.
It’s a perfectly human reflex. Leaders want insight, but also air cover. They want options, but not exposure. A little context, but no confrontation.
The trick, I’ve found, isn’t to push them back into the discomfort too quickly. It’s to meet them there. Reflect their question, not dodge it — and gently offer the mirror anyway.
So I said, “What I’ve noticed is that most organisations don’t really deal with it — not until someone calls the moment. What’s interesting is that we’re already naming it now. That’s the difference.”
There was a pause. A good one. The kind that lets a room breathe before it re-enters the work with just a little more honesty.
Facilitation isn’t always about answers. Sometimes it’s about holding the moment when someone doesn’t quite ask the real question — and giving them just enough safety to circle back around and find it themselves.
In your experience, when do those moments tend to surface — and how do you handle them?
—
Note: All stories are adapted and anonymised to protect client confidentiality.
