Pre-Mortem

A project planning technique where you imagine failure and work backward to identify risks.

A pre-mortem is a strategic planning exercise invented by psychologist Gary Klein. Unlike a post-mortem (analyzing what went wrong after failure), a pre-mortem imagines failure before it happens.

The exercise: 1. Imagine your project has completely failed 2. Work backward: Why did it fail? 3. List every possible reason for the failure 4. Identify which risks are most likely and severe 5. Create mitigation strategies for top risks

Why it works: - Overcomes optimism bias: We naturally underestimate risks - Empowers dissent: Team members can voice concerns safely - Surfaces blind spots: Different perspectives reveal hidden risks

For software development: Pre-mortems are especially valuable because building software is expensive. Common failure modes include: - Building something nobody wants - Underestimating technical complexity - Running out of time or money - Competitive disruption - Poor user experience

AI-powered pre-mortems: Tools like Cutline automate and enhance this process. AI can: - Generate failure scenarios you might miss - Test ideas with synthetic user personas - Identify assumptions you didn't know you were making - Prioritize risks based on likelihood and impact

Examples

  • Running a pre-mortem before starting a new feature
  • Using Cutline to generate AI-powered failure scenarios
  • Team exercise imagining why a product launch failed

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