The chief academic officer (CAO) role is critical to the academic and often administrative mission of an institution of higher education. Key constituents served by CAOs are become more diverse; however the individuals serving in the position are not diversifying at the same rate. The purpose of this study was to collect and portray the narratives, life histories and events of African American women who are currently serving in CAO positions, as a means for discerning the challenges faced by African American women who aspire for the position of CAO. Four African American women, currently serving as CAOs at minority-serving institutions participated in this study. A qualitative methodology, specifically narrative inquiry and autoethnography, was chosen to collect and analyze data from this small, characteristically unique population. Data were collected via telephone interviews, field notes, journal entries and personal written biography. Findings from the study included five themes: (a) Roots to their success, (b) Branches: The Role of Mentoring, (c) Trunk: Life Lessons and Advice to achieve the CAO position, (d) Branches: Perceptions about African American women in academia and (e) Fruits of their Labor: Career Aspirations. Role modeling and mentoring, directly and indirectly related to the CAO position, was important. The narratives provide a roadmap to African American women aspiring to the CAO positions as well as tools for faculty and department chairs in educational leadership/administration preparation programs, and lastly, add to the limited body of literature. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]