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Currently, there is limited research exploring internally developed principal pipeline programs and the effectiveness these programs have in diversifying the leadership workforce. This study uses a representative bureaucracy framework with quantitative and qualitative methods to explore what five large school districts in California are doing to develop educators along the leadership pipeline and how those pipeline programs influence the supply of educators advancing to leadership. Preliminary selected themes suggest an increase in racial and gender diversity in leadership roles across the five participation districts. Early results also illuminate district efforts to address recruitment efforts, investigate common pathways to leadership (e.g., teacher leadership), and show early hiring trends for leadership roles. Analysis is ongoing with preliminary results and implications discussed here.