Residency and fellowship program directors profoundly impact trainees, institutions, and patient safety. Yet, there is concern for rapid attrition in the role. The average program director tenure is only 4-7 years, and that timeline is likely a result of burnout or opportunities for career advancement. Program director transitions must be carefully executed to ensure minimal disruption to the program. Transitions benefit from clear communication with trainees and other stakeholders, well-planned successions or searches for a replacement, and clearly delineated expectations and responsibilities of the outgoing program director. In this Practical Tips, four former residency program directors offer a roadmap for a successful program director transition, with specific recommendations to guide critical decisions and steps in the process. Themes emphasized include readiness for a transition, communication strategies, alignment of program mission and search efforts, and anticipatory support to ensure the success of the new director.