The study reveals the barriers and challenges of African Americans during their ascendancy to senior-level leadership roles. The study addresses the problem of racism and white privilege in higher education institutions related to the underrepresentation of African Americans in senior-level positions, specifically in Washington State community and technical colleges. Despite the passage of landmark decisions and enactment of several laws and regulations, racial discrimination and disparities continue to be a prevalent problem on university and college campuses. The purpose of this phenomenological qualitative study was to explore the paucity of African American representation in these roles. The population was a purposeful sampling of 12 African American senior-level administrators or leaders. Data were collected from eight interview participants and a focus group of four participants of the sampling pool. Critical Race Theory was the theoretical framework selected for this study to understand the factors contributing to the underrepresentation of African Americans in senior leadership positions. The emerging themes indicated that participants perceived barriers and challenges to their ascendancy to these positions which are related to the disparity of African American representation in Washington State community and technical colleges. Racism and race-related issues, feeling of not belonging, gender, and questions of qualification supported the emerging themes stemming from the research questions. These findings shape the basis for the study's recommendations that administrators in higher education institutions implement guidelines or procedures to alleviate the underrepresentation of African Americans and other minorities as well as address racial, diversity, and ethical or equity issues. Recommendations for additional research are presented and include exploring in-depth the barriers affecting ascension of African Americans to senior-level roles and the development of strategies that senior administrators can implement to increase the presence of African Americans in these roles. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]