In this paper, the authors utilize critical reflection and autobiographical narratives as a pedagogical tool for aspiring school leaders to examine beliefs and assumptions on equity and social justice in an educational leadership preparation program. Comparative themes related to their developing social justice and equity orientations included: (a)Understanding heritage and lived experience in relation to inequity and injustice, (b) Positionality awareness as a meaning making tool for leadership development, and (c) Praxis: Aspiration for action in one's leadership role. Incorporating pedagogical tools that engage in difficult conversations with the self and the world has the potential to provided avenues for students to become active interpreters of their past histories, current aspirations and heighten their capacity to be active agents of justice.