The chief residency is a role that can immensely benefit both residency programs and chiefs themselves. For programs, chiefs offer a unique perspective as recent residency graduates and future leaders and can represent and extend the presence of residency program leadership as educators, administrators, and scholars. For chiefs, the chief residency offers a taste of academic leadership and is a take-off point for an informed future in academic medicine. In this chapter, we discuss the types of chief residents in pediatric graduate medical education, typical chief roles and responsibilities, and best practices for the professional development and mentorship of chief residents. We cover recommendations for maximizing the success of the chief year by selecting a cohesive group of chief residents and aligning programmatic goals with those of the chiefs. We encourage chiefs to make their education work scholarly through basic education research principles and offer tips balancing board preparation and clinical work as new attendings with administrative tasks.