Despite an increasingly diverse student population across the United States, the alarming decrease in minority K-12 school administrators (Taie et al., 2022) demands immediate attention. This qualitative study aims to understand the experiences of three different African American school administrators, extracting insights and implications that can be beneficial for school administrators. As we strive to nurture the leaders of tomorrow, our leadership representation must be diversified. Using a case study methodology, the authors employed the Principal Talent Management Framework (George W. Bush Institute, 2020) to examine three cases. Through interviews and transcription coding, the researcher identified themes and action steps that could be utilized to maintain a diverse pool of K12 administrators and reverse the trend of recruiting new administrators of diverse backgrounds into the field. The emerging themes from the study included lack of respect, balance, discrimination, hiring practices, experience, advocacy, calling, intentionality, and mentorship.