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The most useful question you can ask before fall planning begins.
Most leaders begin fall planning by asking some version of the question: What are we trying to accomplish?
It’s the right question. But there’s a second question that most planning conversations skip entirely: Why might this fail?
The Pre-Mortem is a change management tool built around that second question. Rather than evaluating risks abstractly, it asks you to project forward in time: Imagine it’s June of next year, and the initiative you’re planning right now didn’t work. What happened?
The inversion matters. Asking “What could go wrong?” tends to generate vague, defensive answers. Asking “What did go wrong?” puts your brain in narrative mode. You start describing specific failures with specific causes, which is a much more useful input to your planning.
How to run a Pre-Mortem with your team:
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Briefly describe the goal or initiative you’re planning for next year. Keep it to two or three sentences.
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Tell the group: “It’s June 2027. This didn’t work. Why not?” Give everyone two minutes to write down three reasons independently before the group discusses.
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Compile the failure scenarios. Group them by type: resource failures, execution failures, alignment failures, external disruptions.
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For each major cluster, ask: “What’s one thing we could build into our plan now that would make this failure less likely?”
The Pre-Mortem doesn’t predict the future. What it does is surface the concerns your team is already holding quietly, before those concerns become obstacles that no one named until it was too late.
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