Continuing professional development of physicians often revolves around clinical activities. Accordingly, there is a lack of intentional development and support of medical education leaders despite such individuals having critical influence over key organizational functions. Unequivocally, educational leaders have complex and dynamic jobs that require clear delineation of roles, responsibilities, and resources available to successfully train the next generation of health professionals. Although there is guidance on how to longitudinally onboard medical education leaders, there is little information on how to effectively orient such leaders on the functional nature of their jobs. Baylor College of Medicine's medical school dean developed and delivered a 2-day orientation program to educational leaders to clarify roles, responsibilities, and resources. Postevaluation surveys aimed to identify key session content that would be frequently used by educational leaders to oversee key aspects of medical education. The purpose of this article is to outline the structure and content of an orientation program designed for medical education leaders, and share postevaluation data to identify which sessions were most used in practice. Other deans are encouraged to take ownership over the professional development of their educational leaders and delivering similar programming.