This special episode of CFO Thought Leader explores how finance leaders develop not through authority or technical brilliance, but through moments that reveal emotional intelligence. Drawing on recent conversations with Kevin Rubin, Toby Driver, and Bruce Schuman, the episode highlights a consistent pattern: leadership is forged through judgment, empathy, and self-awareness when stakes are high and answers unclear. Structured in two parts, the episode first examines formative moments that reshaped how CFOs think, featuring Shelagh Glaser, John McCauley, and Joe Euteneuer. It then shows how those lessons are applied in practice—through difficult decisions, organizational change, and trust-based leadership under real pressure.