While significant progress has been made in diversifying student demographics and entry-level staff and faculty positions, higher education leadership and decision making remain predominantly European American and male dominated. This dissertation explored this pressing issue by employing a critically interested grounded theory approach. Framed by critical feminism and critical leadership theories, this study explored how women navigate the third space of academic and higher education leadership. The primary purpose of this grounded theory study was to better understand how women navigate the academic third space and pathways to leadership and how organizational structures within higher education institutions influence the feminization of leadership roles and impede career advancement for women. This grounded theory study adopted a social constructionist approach, focusing on investigating the processes of feminizing executive leadership, developing leaders in the third space, and breaking the cycle of patriarchy within higher education institutions. The study situated these processes within the contemporary context of leadership in U.S. higher education in the 2020s. The conceptual framework guiding this research combined critical leadership theory and feminist theory, both of which offer valuable perspectives for understanding and challenging oppressive systems. Data analysis combined constructionist/interpretive and computational grounded theory. This methodological framework leverages both human expertise and computational tools to enhance the rigor and scalability of content analysis. By developing a comprehensive theory that incorporates traditionally marginalized voices, this research challenges the existing structures that have perpetuated exclusion from executive leadership 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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]