There is no evidence that identifies support systems that contribute to the recruitment and retention of Black male K-12 administrators in urban districts. Traditional protocol in the K-12 educational arena often prescribes and requires school administrators to have prior teaching experiences before advancing to a career in school administration. However, within this framework, there is a severely limited pool of Black male teachers in the United States. Thus the opportunity for Black males to become school administrators is woefully inadequate. There are no incentives to attract Black male school administrators such as recruitment programs, scholarship programs, state or federal grants or mentoring programs. Lomotey (1989) conducted a study that asserted Black administrators serve a vital function for all students and for school staff and concluded that it is important to document the accomplishments of these individuals and to encourage both Black men and women to continue to take leadership positions in educational administration. The specific roles Black men and women play as school administrators have important implications for policies and practices in education. Clearly, there is a need for more of these individuals to serve not only Black students but all students. The overarching research question for the study posed to guide the collection of data for this study was to explore factors related to the career of Black male school principals. The interview instrument was a researcher-composed survey which consisted of 28 open ended questions in five distinct spheres of inquiry: (a) family, (b) individual, (c) institutional, (d) community, and (e) comprehensive. Following the development of the interview instrument, a pilot study was conducted to establish the reliability and validity of the researcher-designed instrument. Five themes emerged as a result of the data analysis: 1) colleague support is a key mechanism in the success of Black male school administrators; 2) parental involvement is important in the success of Black male school administrators; 3) connections to the community is important in the success of Black male school administrators; 4) support of higher administration is critical to the success of Black male school administrators; and 5) Access to adequate resources is important to the success of Black male school administrators. Participants responses to the researcher composed survey were the basis of the recommendations set forth in this study.