The case presentation is a time-honored tradition in clinical medicine, and medical journals and national conferences have provided a forum for this type of scholarship for more than a century. Case presentations can also be used by educators as a means to understand challenging learner experiences, and by doing so, lead to advances in the practice of medical education. Medical school faculty are asked to serve in student advisor roles, yet best practices for student advising are not known. Unlike clinicians, who often discuss difficult patient cases, medical educators do not typically have opportunities to discuss challenging student cases to learn how best to support trainees. In this commentary, the authors-from the Johns Hopkins University School of Medicine Colleges Advisory Program (CAP), a longitudinal advising program with the goal of promoting personal and professional development of students—describe the novel quarterly Advisory Case Conference, where medical student cases can be confidentially presented and discussed by faculty advisors, along with relevant literature reviews, to enhance faculty advising skills for students. As medical student advising needs often vary, CAP advisors employ adult learning principles and emphasize shared responsibility between advisor and advisee as keys to successful advising. Unlike traditional clinical case conferences, the Advising Case Conference format encourages advisors to share perspectives about the cases by working in small groups to exchange ideas and role-play solutions. This model may be applicable to other schools or training programs wishing to enhance faculty advising skills.