The purpose of this study was to explore and identify enablers and barriers contributing to African Americans' career advancement into administrative positions at PWIs of higher learning. The analysis yielded 23 emergent themes and eight overall themes regarding the enablers and barriers influencing the career advancement of African Americans at public two and four-year PWIs in Mississippi. The findings from the study suggest the creation of a state and national mentoring program in addition to hiring strategies aimed at growing the pipeline of potential African American administrators could lead to PWIs having a workforce that adequately represents its student population.