This study explored the motivators and inhibitors experienced by women pursuing high school administration positions. Additionally, it sought to identify the reasons behind the gender discrepancies to support improved hiring practices and job requirements and inform districts and states about areas for improvement to attract and retain qualified candidates. This phenomenological study included female high school administrators currently employed in a large, suburban district in eastern Metro Phoenix, Arizona. Initially, all qualified candidates within the district were sent an invitation to participate in the study. The invitation included a questionnaire to collect background information and other professional data. Seven participants were selected: six assistant principals and one principal. The results of this study indicated that women are motivated to pursue leadership positions to impact students positively and are incentivized by the authority and autonomy an administration position provides. However, specific factors that inhibit women from pursuing leadership positions include the lack of a female network, the impact of social norms and gender bias in the workplace, and the lack of work-life balance due to the political nature of the position and the immense time commitments. The findings suggested a need for a formal mentoring process for women in leadership and opportunities for aspiring administrators to develop and strengthen their professional skills. [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.]