This edited volume seeks to interrogate the structures that affect the perceptions, experiences, performance and practices of Black women administrators. The chapters examine the nature and dynamics of the conflict within that space and the ways in which they transcend or confront the intersecting structures of power in academe. A related expectation is for interrogations of the ways in which their institutional contexts and, marginalized status inform their navigational strategies and leadership practices. More specifically, this work explores mentorship as critical praxis; that being, the ways in which Black women’s thinking and practices around mentoring affect their institutional contexts or environment, and, that of other marginalized groups within academe. A discussion of Black women in higher education administration as critically engaged mentors will ultimately diversify thought, approaches, and solutions to larger social and structural challenges embedded within academic climates.