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Although women represent the majority of K–12 educators, their presence dwindles at leadership levels—a phenomenon often described as a “broken pipeline.” This qualitative study explores the lived experiences of women K-12 leaders identifying systemic barriers, personal challenges, and resilience strategies along the pipeline. Through in-depth interviews across diverse districts and roles, the research reveals: 1) institutional gatekeeping and policy misalignments, 2) role incongruence and leadership norms, and 3) informal networks that perpetuate exclusion. Framed within feminist and critical leadership theories, this project offers research-informed remedies—including structured mentorship programs, policy realignment, and equity-centered leadership development—and a pathway to repair by fostering inclusive leadership ecosystems. Findings conclude with actionable implications for educational practitioners, policymakers, and researchers intent on renewing justice in school leadership.