The U.S. Department of Defense has highlighted the importance of preparing health care leaders to succeed in joint, performance-based environments. The current wartime environment, rising health care costs, and an increased focus on joint operations have led to recommendations for Military Health System (MHS) transformation. Part of that transformation will involve improving the identification and development of potential MHS leaders. An examination of how candidates are identified for leadership positions, the training and education opportunities offered to them, and the competencies they are expected to achieve revealed both a range of approaches and several commonalities in the military, civilian, and government sectors. A conceptual framework guided a series of interviews with senior health care executives from a wide range of organizations and military health care leaders from the Army, Navy, and Air Force, as well as a case study of the leader development approaches used by the Veterans Health Administration. Several themes emerged in terms of how leaders are developed in each sector, including the importance of mentoring, career counseling, 360-degree feedback, self-development, and formal education and training programs. Lessons learned in the civilian and government sectors hold importance for transforming the way in which MHS identifies and develops health care officers with high leadership potential for senior executive positions.