Failure, Fearlessness, and Finding Your Edge: A CISO’s Unconventional Path with James Hardie CISO Jeff Deakins

In this episode of The Security Sitdown, we sit down with Jeff Deakins, CISO of James Hardie, for a candid conversation about failure, curiosity, and what it really takes to lead cybersecurity in an AI-driven world.

Jeff shares his unconventional path to the CISO seat from early academic struggles and learning disabilities to leading large organizations through risk, resilience, and rapid technological change. We explore why fearlessness matters more than perfection, how embracing failure shaped his leadership style, and what CISOs can learn from saying “yes” before they feel ready.

The conversation dives deep into AI as both a force multiplier and a threat vector, from automating security operations to rethinking identity, passwords, and breach preparedness. Jeff offers a refreshingly honest take on security awareness, third-party risk, zero trust, and why modern security design must assume humans will make mistakes.

From building AI agents to managing burnout, board conversations, and high-stakes incidents, this episode is a masterclass in modern security leadership — grounded, human, and unapologetically real.

Pull up a chair, it’s time to talk about the human side of cybersecurity.