Why Your Offsite Isn't Working (And How to Fix It)
Too many offsite retreats fail before they begin. Not because teams lack commitment or the venue disappoints, but because leaders try to facilitate their own strategic conversations while simultaneously participating in them.
It doesn't work.
Here's why: The moment you step into facilitation mode, you step out of contribution mode. You're managing the room, watching the clock, navigating dynamics - not wrestling with the hard questions your team needs you to engage with.
The Hidden Cost of Self-Facilitation
When leaders facilitate their own offsites, three things happen:
The loudest voices win. Without a neutral party managing airtime, the same people dominate. Quieter team members - often those with the sharpest insights - stay silent.
Rabbit holes derail progress. Leaders get pulled into tangents because they're invested in the content. A skilled facilitator keeps you on track without killing momentum.
Groupthink takes hold. When the boss is also running the meeting, dissent becomes harder. People read the room, not the agenda.
What External Facilitation Actually Buys You
A strong facilitator isn't there to run your meeting. They're there to free you to contribute and be present for your team.
They create the conditions for honest conversation. They surface what's unsaid. They push back when consensus feels too easy or when the real issue is getting sidestepped.
And crucially, they close with clarity - action items with owners, timeframes, and accountability baked in.
When to Bring Someone In
Not every meeting needs a facilitator. But if you're investing in an offsite, an external voice earns its keep.
The value isn’t in having an outsider in the room. It’s in finally hearing what the room has been trying to say.
Ellie Hearne teaches AI and strategy at Oxford University's Saïd Business School and facilitates offsites for leaders navigating complexity. She serves as a trustee of the University of St Andrews American Foundation.