Leading change that promotes social justice requires courage and conviction. Drawing on identity theory, insights from a New Zealand case study show how two principals found their leadership identity challenged as they resolved issues arising from social disadvantage. The programs they developed to enhance pastoral care, behavior management, and academic achievements were underpinned by a clearly articulated set of values aligned with the principals' values. Findings suggest a focus on intrapersonal factors may be important for leadership preparation and practice. A model is proposed to support critical reflection of personal responses to challenges in leadership practice.