This study focuses on two girls' experiences in one youth leadership organization during a period of 3 years. Relying on an embedded case study design, the authors examine the links between leadership development and programmatic structures and supports. Specifically, the development of leadership capacities are analyzed along three dimensions: communication and interpersonal skills, analytic and critical reflection, and positive involvement in community affairs. Within the leadership organization, the authors consider structures that accommodate and validate different styles of youth leadership and different developmental trajectories, focusing on how these structures evolved along with the leaders they were designed to support. The conclusion discusses the relevance of the lessons that the two girls exposed and that the program internalized to adolescent development research and youth development programming. (Contains 1 figure.)