AI can offer career advice in seconds, but should technology have a say in decisions that can shape an entire life? Charisse Lillie explores where AI-assisted guidance ends and human judgment begins—and why trusted mentors, meaningful relationships, and experienced advisors still matter. Drawing on her new book, Upon a Turning Stage, Lillie shares lessons from a remarkable five-decade career spanning civil rights law, government, corporate leadership, philanthropy, the Federal Reserve, and major corporate boards. Her journey—from growing up in segregated Houston to becoming Philadelphia City Solicitor, a senior Comcast executive, and Chair of the Federal Reserve Bank of Philadelphia—offers a unique perspective on how careers and leaders are built.