The Columbia Academy for Psychoanalytic Educators supports graduate analysts' professional development at the Columbia University Center for Psychoanalytic Training and Research. In 2018, a pilot program was launched for faculty interested in analyzing and supervising candidates, whose aim is to support and educate those interested in taking on these essential training functions. The focus is on educating the educators, which is a significant departure from the historical focus on evaluation, vetting, and faculty hierarchies. In the process of developing and piloting the program, complex and long debated issues in psychoanalytic education and development were considered that are relevant to many institutes, including training of supervisors and analysts of candidates, addressing problematic faculty hierarchies, creating safety for those presenting clinical work to colleagues, building professional peer relationships, and engagement of faculty in time consuming and nonremunerative activities. The authors report on their experience developing and evaluating this pilot program.