In professional practice contexts, the technical questions are rarely the ones that prove most difficult. Rather, the real questions that arise from complex and ambiguous contexts, and that require learners, teachers, and leaders to examine deeply held beliefs about selfhood, integrity, ethics, and justice, often prove to be the most challenging. A recent role-playing simulation in a graduate leadership preparation program demonstrates the tensions between identity and integrity, as well as the pedagogical implications of examining such tensions. This chapter investigates the role of identity in teaching and learning, and draws connections between the process of transformational education and the practice of leadership.