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This case study investigates a school district’s effort to improve the quality and diversity of its principal workforce by standardizing its human resources management (HRM) systems, including hiring, development, and promotion. These reforms were designed to increase transparency and fairness, with the expectation that candidates from historically underrepresented backgrounds would gain greater access to leadership roles. Data sources included 15 semi-structured interviews with district leaders (n=7) and principals (n=8), as well as district policy documents. Findings reveal, despite formal changes, the absence of explicit strategies to recruit and support women and leaders of color allowed gatekeeping barriers to persist. This study shows how leadership reforms must reckon with historical exclusion to meaningfully shape more equitable futures.