This article considers the implications and effectiveness of a performing arts-based pedagogy in the professional development of school leaders. It reports on the findings from a study that exposed educational leaders to methods of dramatic analysis as a means of reflecting on the ethical dilemmas found in personnel management. Through the dynamic enactment of dramatized scripts representing highly charged situations in school leadership, participants came to recognize the limitations of merely discussing cases, the benefits of active learning to developing empathy amid the complexities of schools, and some of the ethical challenges inherent in their roles as school leaders.