The Associate Dean for Students Affairs’ leadership role in medical schools represents an important, critical, and extremely valuable role within the medical school leadership suite. Deans for Students Affairs work closely with the students, leaders, and faculty to ensure students’ success in medical school and beyond. The Deans for Students Affairs are responsible for fostering and supporting an environment where all students thrive. The role comes with a diverse array of responsibilities that include, for the most part, career advising, academic advising, and professional and personal advising. In addition, the Dean for Student Affairs provides oversight and coordinates student events, including orientation, white coat ceremonies, match day, and graduation. The role also requires close collaboration with others within the medical school and active participation in school committees. Many rewards come with the role, including helping students achieve their goals, celebrating milestones, and helping students with personal and professional growth. For those considering this leadership role as their career path, we recommend an intentional assessment of personal values and strengths to align those with the expectations of this role. We conclude with some practical suggestions and resources.