The historical context of education in the United States reveals a consistent failure by American schooling to effectively educate Black boys. Multiple indicators of how Black male students are underserved have necessitated interventions to reverse decades of adverse outcomes. The single-gender school design became one such intervention dedicated to creating validating and affirming educational spaces in response to the educational crisis facing Black boys, with Black male adult school leaders, role models, and mentors being essential components of these schools. The minimal and mixed research on the single-sex approach on behalf of Black students--boys and girls--is reflected in both advocacy for the model as well as critiques questioning its efficacy based on the model assuming a reductive notion of masculinity that calls for Black men only to lead these all-boys schools and programs serving Black boys. Hence, Black women leading these spaces are very rare. This study contributes to the research guided by three questions: (1) What mentorship and role modeling beliefs and actions do Black women school leaders enact as essential for promoting the academic success of Black boys in all-male schools or programs for boys of color? (2) How do African American males who graduated from all-male Black secondary programs led by Black women perceive these women's influence as mentors and role models? (3) How do parents of these former students view the advantages or limitations of Black women leading single-sex, all-male educational environments aimed at supporting the academic and social-emotional growth of their sons? My research design consisted of individual interviews with study participants--women school leaders uniquely positioned as heads of all-male schools and programs serving Black boys, former students of the school leaders, and parents of the former students--guided by open-ended interview questions, focus groups of the former students and parents, environmental scans of the leaders' current school workspaces, and documents review. The data collected generated several important findings highlighted by Motherhood Leadership which was characterized by authentic, humanizing, and caring relationships between the leaders and their students. The women leaders nurtured the boys by creating intentional and organic soft spaces to support their holistic success. Implications for practice and recommendations for future research are discussed. The study honors the legacy of historical excellence of Black women for racial uplift and centers the voices of contemporary Black women leaders often silenced in the educational enterprise of single-sex school spaces designed to benefit Black boys. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]