Thesis advisor: Lauri Johnson / This qualitative case study, part of a larger group study about how leaders support marginalized student populations in a Massachusetts school district, explored how leaders develop and maintain cultural awareness and self-reflection for themselves and for their teachers. The study asked: 1) How, if at all, does the leader develop and maintain critical self-reflection to support marginalized populations? And 2) What leadership practices does the leader enact, if at all, to engage teachers in cultural awareness and self-reflection? Data was gathered and analyzed from 20 semi-structured interviews, including the superintendent, two assistant superintendents, director of bilingual education, two secondary level principals, two elementary level principals, and 12 teachers, and document reviews. Findings indicate that almost all of the leader participants exhibited cultural awareness and reflectiveness which was attributed to either feeling marginalized themselves, or through childhood and professional experiences. Leaders utilized a variety of leadership practices to maintain their awareness, engage in self-reflection, and create more equitable environments for marginalized students, but these practices were not consistent, embedded, or persistent. Implications of this study reveal that district and school leadership practices to enact cultural awareness and self-reflection of leaders and teachers are critical to effectively address inequities and to support marginalized students. / Thesis (EdD) — Boston College, 2020. / Submitted to: Boston College. Lynch School of Education. / Discipline: Educational Leadership and Higher Education.