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This mixed-methods study explores the career aspirations and trajectories of Black female teachers in an urban district, with a focus on advancement into educational leadership. A survey of 380 teachers, analyzed using chi-square tests, revealed a disproportionate inclination among the 48 Black women in the sample toward administrative roles. These findings informed interviews with 11 Black female teachers who shared their professional histories. Among those pursuing leadership, we found divergent paths: some advanced quickly, while others experienced delays despite meeting state requirements and applying for positions. A key theme across interviews was the role of “tapping” (informal recruitment and sponsorship) as a mediating factor in career advancement. The study highlights systemic barriers and opportunities to support Black women’s leadership pathways.