The issue that this study addresses is the lack of Chicana/os in higher education leadership positions. In response to this issue, the purpose of the study is to understand the experiences and draw perspectives from successful non-faculty Chicana/o higher education leaders to identify the individual, cultural, organizational, and environmental influences that may inhibit or facilitate the transition of Chicana/os to leadership roles. This qualitative critical narrative study conducted interviews with 11 Chicana/os in administrative leadership roles. Findings determined that individual, workplace, and systemic influences positively and negatively influence Chicana/o professional advancement. These influences include community cultural wealth, personal growth, workplace environments, hiring, and institutional discrimination. Taken together, the findings and recommendations of this study provide valuable contributions to the body of knowledge addressing the lack of inclusion of Chicana/os in postsecondary leadership roles, assist aspiring Chicana/os seeking leadership, and help educate entities seeking to create college university leadership spaces that are more inclusive of Chicana/os. [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.]