Historical analyses of educational attainment trends have revealed disparities concerning Black males, particularly with respect to attainment of advanced degrees. The purpose of the present study was to identify critical factors that promoted educational attainment of advanced degrees among ten Black men who were leaders within educational organizations and had earned at least one advanced degree. The present study was grounded in understandings related to social cognitive theory and considered the distinctiveness of the Black male experience. Using a phenomenological qualitative research design, data were analyzed using a grounded theory approach, which led to the identification of three themes: (1) supportive social networks; (2) aspects of cultural identity; and (3) self-beliefs. A discussion of findings summarized favorable and unfavorable critical factors that emerged from data analyses and pointed to implications for graduate program stakeholders regarding educational resilience and leaders within educational organizations regarding the recruitment, retention, and development of Black male leaders. Recommendations for future areas of research were provided, as well as limitations with the present study.