Leadership Insights

Planning Forward by Imagining Backward

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The business professionals planning the company strategy

Leadership Insights

 

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:

  1. Briefly describe the goal or initiative you’re planning for next year. Keep it to two or three sentences. 
  2. 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. 
  3. Compile the failure scenarios. Group them by type: resource failures, execution failures, alignment failures, external disruptions. 
  4. 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. 

This is particularly worth doing in higher ed, where long lead times between decisions and outcomes can make it easy to defer hard conversations. A Pre-Mortem in June, before commitments are made, creates permission to ask difficult questions in a low-stakes environment. 

Pause & Reflect 

Pick your most significant initiative for next year. Imagine it’s June 2027, and it fell short. Write down three specific reasons it might have done so. For each one, ask yourself: “Is there something I could do this summer to reduce that risk?” 

Pro Tip: You don’t have to wait for a formal team meeting to try this. Enter this prompt into Sophia“Help me run a Pre-Mortem on [brief description of your initiative]. Generate five plausible failure scenarios I should stress-test before fall.” 

Learn more about leading change in Lessons from the Work, a recent paper by Amit Mrig.