Why Most Leadership Offsites Don’t Work — And What To Do Instead
Aug 28, 2025
Based on what clients tell me, most leadership offsites don’t just miss the mark — they leave people more drained than developed.
They’re not failing by a little. They’re failing by a lot.
Leaders come in hoping for clarity and connection. They leave feeling tired, unheard, and no closer to solving what really matters.
Why? Because most offsites don’t actually change anything.
They just turn up the volume on business as usual.
When BAU Turns Into BS
It usually sounds like this:
“Now that we’ve got everyone together, let’s power through the same issues we’ve already been talking about.”
Same conversations. Same PowerPoints. Same anxieties.
Just in a nicer venue. With better food.
Instead of making space for real thinking and stronger relationships, the agenda gets packed and overly controlled.
The result? Leaders leave more disconnected — not less.
What a Great Offsite Actually Looks Like
When offsites work, they don’t feel like work. They feel human.
Here’s what I’ve seen from the rare, high-impact ones:
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Leaders let go of the pressure to perform and start to reflect.
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The team builds genuine trust — not through forced games, but real conversation.
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The focus shifts from my role to our impact.
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There’s time left open — not as filler, but as fuel for the kind of conversations you can’t script.
Think about your best weekend away with friends.
It’s never the second day’s agenda that creates connection. It’s the unscheduled, free-flowing chat on night one that opens everything up.
Leadership offsites can feel the same — if you let them.
What to Do Differently
If you're planning an offsite, here's the most useful advice I can offer:
Stop over-planning it.
Make the offsite the plan. Create the right conditions — then trust the people in the room to surface what really needs to be said.
The results? Deeper trust. Clearer alignment. And more commitment to what happens next.
Work with James to Design an Offsite That Actually Works
If your team needs something real — something that builds connection, trust, and direction — I can help you design an offsite that people will remember for the right reasons.
Let’s talk — email [email protected]