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This paper investigated how organizational elements and mechanisms, such as structural policies, procedural practices, and cultural norms, influenced leadership diversification efforts in one school district. Applying Ray’s theory of racialized organizations, I examined leaders’ perceptions of implementation mechanisms in Cascade Hills School District and their effects on diversification initiatives. Through 17 semi-structured interviews with district leaders, the study uncovered how racialized mechanisms such as loose coupling and organizational culture shaped the experiences of loC. Findings revealed challenges in coherence, inconsistent practices, and resistance to change, which affected the effectiveness of leadership diversification efforts. This paper provided insights into systemic barriers faced by loC and highlighted the need for cohesive, equity-centered organizational approaches to sustain a diverse leadership workforce.