podcast 030: the leadership skill that AI can’t replace
In today’s episode, Deb sits down with longtime friend and former Big Law CIO Bob Craig for a conversation that starts with AI but quickly becomes something deeper: identity, approval, and what it really costs to be “the steady one” in every room.
“My obsession with outcomes was all about earning approval. I missed a lot of joy in the journey and that’s where human flourishing shows up.”
Bob has spent four decades guiding people through wave after wave of tech disruption. But in this season, he’s doing a different kind of work turning inward, processing regret, and building a small, intentional community to explore what it means to stay fully human in the age of generative AI.
Together, Deb and Bob unpack the hidden driver behind high performance (and why it can quietly hollow us out), the difference between burnout and fragility, and why the most important leadership skill now might be learning to hold contradictions without forcing an answer. Bob introduces “the liminal mind,” a way of thinking that lives on the boundary between the coded and the intuitive, and shares a manifesto that feels like a call to presence, not productivity.
Key Highlights:
Bob’s honest reframe: how “people-first leadership” can be fueled by a quiet hunger for approval and what happens when you finally see it
The moment he realized he’d stepped away too early, why regret isn’t the problem, and how processing it becomes fuel for flourishing
The Liminal Mind manifesto: a boundary-walking approach to being human alongside AI without defaulting to binaries or panic
The four primal powers (intuition, imagination, emotion, common sense) and why emotion might be the leadership superpower everyone keeps avoiding
A simple 30-day practice for anyone who feels “off”: nature walks with no headphones + one question that keeps getting sharper the more you ask it
About Our Guest:
Bob Craig is a former Chief Information Officer and technology leader with a 40-year career guiding large organizations, especially law firms, through digital transformation. In his current chapter, Bob is focused on presence-based coaching and on exploring the intersection of artificial intelligence and human flourishing through his work with The Liminal Mind Collective.
About The HX Collective:
The HX Collective is a movement to elevate the human experience—at work, in relationships, and with ourselves. Through honest conversations and strategic insight, we explore how connection, context, and compassion can create a more flourishing world, starting right where we are.
