A strategic pre-mortem is a collaborative exercise where participants imagine a project has already failed. Rooted in the work of Gary Klein, this practice encourages teams to work backward to diagnose hypothetical causes of failure. It leverages the expertise of stakeholders—including skeptics and domain experts—to surface concerns in a structured, non-confrontational environment. The exercise can be applied to projects of any scale, from large strategic initiatives to smaller tasks.

The objective of a strategic pre-mortem is to proactively identify potential risks and failure points in a project or initiative before it begins. By simulating a future failure scenario, teams can uncover hidden challenges, mitigate risks early, and increase the likelihood of project success.

• Learn from past failures: Identify and address historical patterns of failure.
• Engage experts: Involve critical thinkers who might otherwise be overlooked.
• Mitigate risks early: Proactively resolve issues before they escalate.
• Boost buy-in: Foster ownership and alignment among stakeholders by addressing concerns upfront.
• Save resources: Avoid wasted effort by addressing potential pitfalls during planning.

Preparation

1. Gather materials: Collect project plans, lessons learned documents, purpose statements, and other relevant artifacts.
2. Select participants: Include leaders, key team members, and skeptics with domain expertise.
3. Set expectations: Communicate the session’s goal: “Imagine this project failed—why did it happen?”

Session Execution (60–90 minutes)

1. Clarify the goal:

   • Have a stakeholder briefly articulate the project’s objective. Ensure alignment among participants.

2. Review the plan:

   • Present the high-level project plan. Confirm shared understanding.

3. Discuss past failures (optional):

   • Ask participants to list similar past initiatives and their failure reasons. Capture insights.

4. Simulate failure:

   • Instruct participants to write down hypothetical reasons for failure (e.g., “Poor communication” or “Resource shortages”).
   • Share and group these reasons on a “What Went Wrong?” canvas.

5. Prioritize risks:

   • Plot risks on a likelihood/consequence matrix. Focus on high-impact, high-probability risks.
   • Discuss mitigations (e.g., “Assign a dedicated project manager” or “Secure budget approval upfront”).

6. Assign actions:

   • Document actionable steps to address risks. Assign owners and deadlines.

Post-Session

• Track actions: Schedule follow-ups to ensure accountability.
• Update documentation: Transfer insights to team knowledge bases for future reference.
• Onboard new members: Use pre-mortem outputs to quickly align newcomers.

Async Facilitation Tips

• Use surveys or collaborative tools (e.g., shared docs) to gather input asynchronously.
• Balance async work with brief check-ins to maintain momentum.
• Document constraints and decisions clearly for remote participants.