Welcome back to Five Questions for a General, a production of the Modern War Institute at West Point. This series features specially selected cadet hosts who are given an incredible professional development opportunity—to sit down with senior military officers and ask carefully crafted questions about everything from leadership to their unique experiences while serving, to their expectations about the future of war. In this episode of Five Questions for a General, Cadet Donovan Scott sits down with retired Major General Bill Rapp for a wide-ranging conversation on leadership, decision-making, and the challenges of driving change in large organizations. Drawing on more than 30 years of Army service, including combat deployments, his tenure as commandant of West Point, and command of the US Army War College, General Rapp offers candid reflections on the lessons that shaped him as both a soldier and a leader. From steering cultural change in academic and operational settings, to managing seemingly impossible logistical challenges in Afghanistan, to championing humility and courage as the bedrock of leadership, General Rapp provides wisdom that resonates far beyond the military. Whether discussing cadet snowball fights at West Point or the moral courage required to change course when plans fail in combat, his insights blend humility, humor, and hard-earned perspective. This episode is a must-listen for anyone seeking practical lessons in leadership, resilience, and collaboration.