"The trap of thinking ahead"

As leaders, we’re told to prepare. Think things through. Anticipate problems.

But there’s a trap in this.
When we spend time alone turning a problem over, we come into the room with conclusions already forming. Then we drop a question into the mix:
​“So, what do you all think about the process?”

To us, it sounds open. To them, it feels loaded. They sense we’re ahead of them, maybe already decided. Instead of a conversation, it becomes a test. Silence is safer than contradicting.

This isn’t bad intent, it’s a timing gap. We’ve had time to reflect. They haven’t.

So how do you avoid collaboration theatre?

A few ways I’ve found helpful:

• Name your prep. Be honest that you’ve been thinking it through. Don’t pretend neutrality.
• Share your angle, not your answer. Frame your conclusion as a perspective, not the perspective.
• Level the time imbalance. Give people a few minutes to jot down thoughts before discussion.
• Ask concrete questions. Broad “what do you think?” invites silence. Specific prompts invite dialogue.

The real point? Curiosity isn’t just about asking questions. It’s about creating conditions where others can join you, without feeling like they’re already behind.

Until next time,
Dermot
The Messy Middle.

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