Most product failures happen because teams underestimate risk, navigate around stakeholder objections, miss second-order consequences, or commit too early to a narrow framing of the problem. Premortems reverse this dynamic. Instead of asking why a project might succeed, teams imagine that the initiative has already failed and work backward to uncover the causes. Long before modern product teams existed, Stoic thinkers practiced the premeditation of evils, mentally rehearsing what could go wrong so they could make better decisions in the present. Today, organizations that are willing to imagine that a project has already failed and work backward to uncover the causes, increase their odds of success. Instead of waiting for a retrospective to evaluate a plan in hindsight, agile teams should be running pre-mortems to anticipate risks and create plans to mitigate them should they become real. In this session, I will show how to combine this proven decision technique with generative AI to dramatically expand the range of risks a team can surface. Attendees will learn how AI can help expand their field of vision to see vulnerabilities, explore what happens when assumptions are flipped, and identify hidden biases that might undermine success. Product leaders will leave with a practical framework, and a reusable worksheet, for running high-impact premortems using GenAI—helping teams anticipate failure, strengthen strategy, and fortify product plans.