In cybersecurity, anticipating the worst isn't paranoia—it's strategy. This session introduces creative thinking frameworks designed to help leaders and security teams collaborate with Generative AI to stress-test assumptions, identify opportunities, explore edge-case risks, and uncover blind spots, often caused by cognitive biases, before they become breaches. 

Drawing inspiration from Stoic philosophy’s premeditation of evils—the practice of imagining future harms to build resilience—this talk repositions GenAI from its role as an operational efficiency tool to one where it serves as a creative partner in strategic planning. We’ll explore how GenAI can enhance your strategic imagination through various techniques that will expand your field of vision. Attendees will leave equipped with actionable tools for improving red teaming, scenario planning, and creative problem-solving.