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In medical education, evaluating outcomes from programs intended to transform attitudes or influence career trajectories using conventional methods of monitoring is often difficult. To address this problem, the authors adapted the most significant change (MSC) technique to gain a more comprehensive understanding of the impact of the Medical Education Partnership Initiative (MEPI) program at the University of Zimbabwe College of Health Sciences.In 2014–2015, the authors applied the MSC to systematically examine the personal significance and level of positive transformation that individuals attributed to their MEPI participation. Interviews were conducted with 28 participants nominated by program leaders. The authors coded results inductively for prevalent themes in participants’ stories and prepared profiles with representative quotes to place the stories in context. Stakeholders selected 9 themes and 18 stories to illustrate the most significant changes.Six themes (or outcomes) were expected, as they aligned with MEPI goals—becoming a better teacher, becoming a better clinician, increased interest in teaching, increased interest in research, new career pathways (including commitment to practice in Zimbabwe), and improved research skills. Three themes were unexpected—increased confidence, expanded interprofessional networks, and improved interpersonal interactions.The authors found the MSC to be a useful and systematic evaluation approach for large, complex, and transformative initiatives like MEPI. The MSC seemed to encourage participant reflection, support values inquiry by program leaders, and provide insights into the personal and cultural impacts of MEPI. Additional trial applications of the MSC technique in academic medicine are warranted.