A "pre-mortem" is a powerful strategic exercise. Instead of asking "What could go wrong?", you assume "The project has already failed" and work backward to determine the most likely causes. This shift in perspective often uncovers risks that a standard brainstorming session might miss.

You can supercharge this process by feeding an AI the details of a real past project that struggled, asking it to find parallels.

The Strategy: Combining Imagination with Historical Data

This prompt asks the AI to take on a creative, pessimistic persona and connect its imagined failures to concrete data you provide.

Step 1: Anonymize a "Lessons Learned" Document Find a post-mortem document from a past project that was late, over-budget, or failed to meet its goals. Remove all names and sensitive project details.

Step 2: Craft Your "Pre-Mortem" Prompt Now, write a prompt that sets the scene for failure and asks the AI to connect it to your past experiences.

Example Prompt:

"Act as a cynical but brilliant senior supply chain analyst writing a 'pre-mortem' report.

Our New Project: We are about to start a project to build a new distribution center in Texas. The entire project's success relies on a single, specialized crane that we are leasing from a small, regional equipment provider.

Your Task: Imagine it's one year from now, and this project is a complete failure. Write a short pre-mortem report explaining what went wrong.

CRITICAL: In your report, you must draw direct parallels to the problems we faced in our 'Western Region Warehouse' project, described below.

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Past Project Failure Context: [Paste your anonymized data from the past project here] ---"

⚡️ The AI-Generated Report

This technique forces the AI to move beyond generic failure modes. It will use the specific details you provided to create a chillingly plausible scenario. This provides you with a clear, high-priority risk to address immediately: vet the equipment provider's maintenance record and identify a backup vendor before breaking ground.

This is another example of a safe way to use public AI tools, as all sensitive data has been anonymized. The true enterprise solution, however, would be a tool like Microsoft Copilot, which could securely access all of your past project documents on SharePoint and generate this pre-mortem without you needing to copy, paste, or anonymize anything.