Representations of Black leaders in the provost position are few, which speaks to historic views on Black intellectualism, barriers to administrative service, and a lack of professional networks and mentors. In this essay, Russell S. Thacker and Sydney Freeman Jr. examine the lived experiences of thirteen current and former Black provosts at predominantly White institutions and outline strategies to help other aspiring leaders of color prepare for senior administrative positions in higher education. They highlight the unique barriers faced in the preparation and service of Black provosts and also reveal positive evidence that institutions are increasingly open to the diverse backgrounds and contributions brought by leaders of color.