Black superintendents are significantly underrepresented in our nation's schools. Despite a slight increase in representation of female Black superintendents, minorities of all races continue to be underrepresented (Tienken & Domenech, 2020). In this study, I examined the experiences of Black superintendents in Michigan who currently hold superintendent roles, along with the obstacles they faced and their personal characteristics and associated factors that attributed to their resilience and longevity in their role as superintendent. Using a phenomenological qualitative study approach of personal and confidential interviews and survey questions of 12 Black superintendents, data was collected to formulate a toolkit for aspiring Black superintendents. The purpose of this study serves to increase the representation of minorities to equal that of the increasingly diverse student populations and provide equity in the top leadership position in K-12 education. Three major themes explored in this study included: (1) external support systems needed for confronting obstacles; (2) hiring practice preparation; and (3) adequate and effective programs for the recruitment and retention of Black superintendents. These findings will be valuable to the aspiring Black superintendent candidate and will also serve as relevant insight for superintendent search firms and school boards to prioritize diversity and recognize their own biases and seek intentional policy changes that would provide opportunities for aspiring Black leaders to further their careers. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]