The aim of this phenomenological study was twofold. The first was to identify the reasons why female teachers are not interested in becoming administrators, namely to understand why they are not interested in this position. The second was to uncover what problems women administrators face and understand if these problems are influencing their decision not to pursue administrator positions. The participants were 26 female teachers and 17 female administrators working in different types of schools. The research data were collected through semi-structured questions and analyzed using the content analysis method. The majority of obstacles experienced by female administrators are the same ones seen as obstacles by female teachers. Despite no legal barriers to women becoming administrators, functional reasons underrepresent women in school administration. The reasons why female teachers don't want to become school administrators were due to family responsibilities, fear of economic losses, difficulties with female colleagues, heavy workloads and responsibilities, difficulty balancing work and private lives, difficulties with administration, and parent problems. Finally, some recommendations were proposed to overcome the reported issues.