There's a lot of hype around failure in the business world, "Fail fast, fail often". It's true that most significant accomplishments come after hundreds of mistakes and failures. As a competitive rock climber and coach, I have integrated extreme failure safely into my process for progression in the sport. How can a software development organization embrace failure in an intelligent way? This presentation will illustrate Lean, Agile, and Extreme Leadership concepts related to failure, rapid proto-typing, and feedback loops through the metaphor of professional rock climbing and with real-life case studies from IT projects.