E14 | How to Balance Human Connection and AI in Leadership Coaching | Andrea Chilcote

In this episode we explore how leaders navigate overwhelm and uncertainty while sustaining connection, learning, and forward motion. We discuss practical coaching habits — listening with empathy, pacing conversations so people are ready to move from grief to rebuilding, and using foresight to prepare for multiple scenarios. We examine how leaders balance human connection with technology adoption, when AI can augment basic coaching and when human wisdom and intuition remain essential. Listeners will leave with concrete prompts for empathic conversations and steps to coach change into their teams.

Andrea Chilcote brings three decades of executive coaching and organizational development experience as founder and CEO of Morningstar Ventures. She synthesizes frontline leadership work with research on post-pandemic needs and has written What Leaders Need Now to capture practical guidance for turbulent times. Andrea helps leaders build resilience, improve team cohesion, and align development practices with strategic change. Her focus on listening, empathy, and pragmatic foresight models the coaching mindset we recommend for sustaining engagement and catalyzing recovery.

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