This article examines how coaching and reflection contribute to a leadership development plan as applied to graduates of a faculty fellowship medical program. Specifically, the authors’ focus is on reciprocal coaching with respect to the implementation of a leadership development plan (LDP). A qualitative inquiry was conducted to evaluate program effectiveness, though the research also included a cohort comparison of LDP implementation. The authors indicate that program results improved participant’s emotional and functional skills, their ability to give and receive reciprocal peer coaching, and enhanced overall coaching skills.