This research had two basic objectives: (1) To shed light on the factors that contribute to attaining a middle management position (including facilitating circumstances and impediments); and (2) to uncover the experience of Black men once they attained such positions (supervisory experiences, and race relations). Data were collected from twenty-three managers employed at 20 distinct organizations (15 middle managers and 8 managers of others) using semi-structured interviews conducted by the author. Participants completed a demographic questionnaire detailing biographical and career information. The findings included information about developmental relationships, pressures of middle management, the impact of race and gender on dynamics with supervisors and direct reports, and the nature of intraracial relationships within organizational settings. The qualitative analysis revealed the benefits of developmental relationships across race and gender group memberships, the differences between interracial and intraracial relationships with subordinates, and the costs and benefits of an incongruent expressed racial identity. Implications for those who work for and consult to organizations and their employees are discussed in addition to suggestions for future research.