The roles that program leaders establish in their relationships with youth structure how leaders are able to foster youth development. This article examines the complex roles program leaders create in youth programs and investigates how they balanced multiple roles to most effectively respond to the youth they serve. Analyses of qualitative data from 12 high quality programs for high school-aged youth suggest that program leaders take on different roles. In some cases, youth experienced their program leader as a trusted friend, caring parent figure, or influential mentor. In other instances they described him or her as having the knowledge and authority of a teacher or boss. Analyses further suggest that moving across multiple roles appeared to make the program leaders more effective. (Contains 2 tables and 4 notes.)