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There exists a variety of programs designed to prepare future leaders. In the arena of graduate programs in leadership, the International Leadership Association (2020) provides over 350 programs in their database. Guthrie and Jenkins (2018) have outlined dozens of strategies for leadership education that are utilized in degree programs. As such, there exists a need for informed choices when experiential learning pedagogies are incorporated in leadership education curriculum. One methodology, known as case-in-point, was designed at the Harvard Kennedy School to teach adaptive leadership (Heifetz & Linsky, 2017). There lacks empirical research in demonstrating the effectiveness and impact of case-in-point pedagogy. This qualitative study explored the perceived impact of 12 alumni who took a case-in-point course embedded in a leadership master’s program across a decade. Alumni’s retrospective experiences were collected to understand the impact the course had on them during the time they were in their leadership program and the impact of the learning for their professional lives. Key themes that emerged from the participants included increased levels of awareness in race and power dynamics, an increased use of self-as-instrument, awareness of relationships to authority, and shifts in views of leadership. All participants viewed the case-in point pedagogy as powerful or positive after having graduated from the program despite many recollections of mixed or negative experiences during their time in the course/s. Implications of the findings suggest important considerations relating to scaffolding and proper processing to enhance or improve outcomes for case-in-point pedagogy designed to enhance leadership ability.