In Division III athletics, women hold 30% of athletic director positions, a percentage that has decreased when women held 90% of athletic director positions for women's athletics in 1972, which was the enactment of Title IX (Acosta & Carpenter, 2014). This study used role congruity theory as its conceptual framework to examine how stereotypical views of female behavior affect women who aspire to athletic director positions in Division III athletics. This was a qualitative study using a multiple case study methodology. The study was based on research questions that reflected on the underrepresentation of female Division III athletic directors. All female Division III athletic directors who held at least a bachelor's degree were eligible to participate in the study. The interview questions consisted of open-ended questions that explored gender roles, leadership styles, and obstacles that influenced the participants' workplace behavior and other experiences regarding their leadership roles. This study finds that the lack of women in Division III athletic director positions is not entirely due to a bias against the female gender. Rather, women need to possess the agentic characteristics deemed necessary for holders of the athletic director position that are typically found more naturally in men. As athletic directors, women offer a true Division III experience for their staff and student-athletes by capitalizing on their natural communal traits; but, from a hiring perspective, their agentic qualities are what secured them their positions. [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.]