A business wargaming consultant knows that the most dangerous sound in a boardroom is less disagreement than the silence of assumption, that is, the moment when a company’s success becomes so familiar it feels like destiny. This case study introduces the pre-mortem, a strategic exercise designed to shatter this complacency by transporting leaders into a future where their organization has already failed. Unlike traditional risk analysis, which asks “what could go wrong?” and generates predictable checklists, the pre-mortem sets participants in the future and asks “what happened?” This subtle shift forces executives to construct a narrative of collapse, revealing the messy, nonlinear interactions between a wide range of forces that standard models miss. This is not about cultivating pessimism but the ability to celebrate current success while simultaneously exploring how it might unravel, turning the fear of disruption into the creative capacity to reinvent before the storm hits.