Despite a tremendous increase in sport participation opportunities for women and girls over the previous decades, women are highly underrepresented in leadership roles throughout the sport industry. This underrepresentation has been attributed to a variety of social and cultural barriers faced by women in this male prominent industry, and while these barriers to leadership advancement are well established in literature, individual perceptions of the barriers and obstacles are not well known. Given that men hold the majority of NCAA sport leadership roles, it is critical to evaluate employee perceptions of the barriers to sport leadership advancement for women as networking opportunities, hiring practices, and the effectiveness of organizational diversity initiatives may hang in the balance. As a result, and to fill this gap in the previous literature, the Career Pathways Survey was utilized to gauge employee perceptions of the barriers. Overall, findings revealed that men administrators were less likely to acknowledge the existence of leadership barriers for women employees. Based on these findings, we argue that symbolic organizational structures/policies are falling short of advancing Equal Opportunity Law towards social and cultural change. Implications are discussed along with suggestions on how to improve upon the arguably unsuccessful symbolic structures/policies that sport organizations have implemented to improve their levels of diversity.