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This study explores the ways in which the politics of race, diversity, and social justice inform the principal preparation and leadership development of Black principals and other senior educators. Through a qualitative, phenomenological study and in-depth semi-structured interviews, the research presents humanized portraits of Black leadership and leadership development as described by four Black senior educators. Critical race theory and historicizing of knowledge are connected with culturally sustaining pedagogy to ensure cultural sensitivity. The research also draws on African-centered leadership development models, as well as the role of Civil Rights activism and advocacy as part of leadership praxis, to inform the inquiry. Centering the dominant paradigms of leadership, the research presents more expansive and inclusive paradigms of leadership development.