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, retired Major General Doug Crissman reflects on more than three decades of Army service and the leadership lessons that endured from West Point through combat, senior command, service alongside the British Army, and life after the uniform. In this conversation with host Cadet Orion van Buskirk, General Crissman argues that great leadership rests less on rank or authority than on authentic connection, competence, trust, and a willingness to keep learning. He discusses why mission command remains an aspirational goal that leaders must continually rebuild, why leader development should happen every day rather than during designated events, and how setbacks often provide more valuable lessons than successes. He also offers a candid look at retirement and purpose, describing his continuing work mentoring military and civilian leaders—and the grounding experience of simply being “Doug” while selling outdoor gear in his post-Army years. General Crissman's message for leaders at every stage is straightforward: focus on what matters, invest in people, learn continuously, and find the work and relationships that fill your tank.

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, Cadet Zach Olson speaks with Major General James Bartholomees, the commanding general of the 25th Infantry Division, about the leadership philosophy that has guided him from the Ranger Regiment to division command. The conversation also covers the Army's ongoing process of transformation for future conflict, and the strategic importance of the Indo-Pacific. Drawing on decades of experience, General Bartholomees explains why discipline, leader initiative, and strengthening soldiers through personal connection remain timeless leadership principles, even as the character of warfare rapidly evolves through developments like drones, electronic warfare, and artificial intelligence. The discussion concludes with an exploration of wide-ranging topics such as deterrence in the Pacific, the lessons of Ukraine, Operation Pathways, the importance of sustainment, and why tomorrow's leaders must combine mastery of fundamentals with curiosity, adaptability, and a commitment to continuous learning.

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.

This episode features Major General Wolfe Davidson, commander of the US Air Force's training enterprise, in a wide-ranging discussion with Cadet Zach Olson about leadership, joint warfighting, innovation, and preparing the next generation of airmen for an increasingly contested battlefield. Drawing on more than three decades as a special tactics officer and senior leader—including assignments supporting US Space Command, the Defense Threat Reduction Agency, and the chief of staff of the Air Force—Davidson explains why modern warfare demands leaders who understand all domains of conflict, embrace joint and coalition operations, and balance innovation with disciplined execution. He shares insights on transforming Air Force basic training for the first time since the Korean War, building trust and accountability within military organizations, the importance of broadening assignments and professional education, and why understanding the why behind the mission is essential for developing adaptive leaders capable of winning tomorrow's wars.