To build capacity for students in educational leadership programs, we developed a teaching case study focused on managing emotion for ethical decision making in supervision of personnel. The case offers troubling encounters between a secondary assistant principal and a novice teacher, a veteran teacher, and a veteran administrator. Scenarios include issues of confidentiality, politics, and the tension between educators' professional ethical principles and an established more laissez-faire school climate and culture. Readers are guided to consider the role of emotion in leadership and how self-reflection can be used as a process for managing emotion.