Research that examines the lived experiences of Black senior level student affairs administrators at predominately white institutions remains limited (Wolf & Freeman, 2013). The underrepresentation of administration of color in higher education is one of the most important ethical dilemmas facing colleges and universities today (Wolf & Freeman, 2013). This study explored the lived experiences of Black senior level administrators at predominately white institutions, their race relations, and challenges faced. The findings from this study show variations in the experiences of Black senior level administrators who have excelled to their roles despite the lack of visual representation. Very few studies have explored or have sought to discover the experiences of Black senior level administrators in student affairs and what their experiences have been leading at predominately white institutions, racial relations, and their overall challenges they have faced to get to where they are and since they have been in their roles. Ten Black senior level student affairs administrators in the Southern Association of Colleges and Schools Commission on Colleges region were interviewed for this study. Three overarching themes emerged from this study: (a) Cultural Mirror; (b) Interpersonal Relationships; and (c) Transformation. Each of these themes express the experiences that Black senior level administrators cycle through during while in their role. Critical Race Theory (CRT) was used as a theoretical framework for this study as it looked at the telling the stories of Black administrators. The result of this study suggests there are unique experiences that Black administrators go through on their journey to higher level roles. This study also informs us of the varying leadership styles, challenges and how race shapes the relationship experiences of leaders. [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/en-US/products/dissertations/individuals.shtml.]