What if the key to building resilient plans isn't optimism—but deliberately imagining failure?
In this game-changing conversation, we sit down with Leslie Grandy, a global product executive with 25+ years leading innovation at T-Mobile, Apple, Best Buy, and Amazon. Leslie is the founder of The Product Guild, Lead Executive in Residence at the University of Washington Foster School of Business, and author of the just-released book Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI (Wiley, May 2025).
This isn't another "AI will automate your tasks" conversation. Leslie introduces a radically different approach: using generative AI as a strategic partner to challenge assumptions, stress-test plans, and imagine failure scenarios your team is psychologically unwilling to consider.
Drawing on the ancient Stoic practice of "Premeditation of Evils," Leslie shows how deliberately imagining what could go wrong builds genuine organizational resilience and accelerates innovation.
In this episode, we explore:✨ Why humans are psychologically unwilling to plan for failure—and how this blindspot derails billion-dollar projects
🤖 How to reposition Gen AI from efficiency tool to creative collaborator in strategic planning
🏛️ The ancient Stoic practice that modern leaders need to future-proof their organizations
🎯 Practical frameworks for stress-testing plans using AI's "psychological distance"
🏢 How to embed resilience thinking as organizational culture, not just individual practice
Whether you're launching a product, managing a complex project, or leading organizational strategy, this conversation will fundamentally change how you think about risk, resilience, and the strategic role of AI.
Challenge for this week: Pick one project. Open your AI tool. Ask: "What am I not seeing? What could go wrong that I'm unwilling to imagine?"
🎧 Listen now and discover how to build plans that don't just survive the future—but thrive in it.
