To gain an in depth understanding of the youth leadership development process in sport, qualitative interviews were conducted with high school coaches (6 males; 4 females) known for cultivating leadership in their captains. Hierarchical content analyses revealed that all of the coaches reported proactive approaches toward teaching leadership through sport. However, based on the principles noted in the positive youth development literature, these coaches could do more to enhance their leadership development practices (e.g., empowering captains by more often involving them in important decision-making). Leadership philosophies, specific leadership training strategies, as well as the biggest challenges and mistakes when working with their captains are reported. Directions for future research and structuring captain training programs are discussed.