To be effective social justice leaders, school leaders need to gain critical understandings of their positionality and racial privilege and be prepared to engage in difficult conversations with others. This study examines how a peer-to-peer letter exchange assignment in a doctoral course allowed educational leadership doctoral students (N = 27) to reflect on race and privilege with each other. The findings reveal how students examined racial privilege, positionality, and bias. The authors discuss how this assignment can be used in educational leadership programs to develop and grow the practice of critical reflection for self-examination of privilege.