Optimism bias can frequently present challenges to in-house counsel, making standard legal assessments feel like an attack on a project the business team is eager to launch. Olivier Sibony’s book You're About to Make a Terrible Mistake! introduces the "Premortem" as a highly effective tool to address this exact friction in corporate risk management. While the book offers an array of strategic frameworks, this specific concept stands out for its practical ability to make constructive dissent socially safe within an organization. Instead of asking, "What could go wrong?",  which can inadvertently position Legal as a roadblock, the premortem uses prospective hindsight (p. 224). Before a final sign-off, gather the project team, look forward in time, and frame the discussion as: "Imagine we are three years into the future, and this project has failed spectacularly. It is an absolute disaster. Now, everyone take 10 minutes and write the history of how it failed...