Despite widespread alarms about a growing shortage of school leaders, an obvious source of well-prepared talent continues to be overlooked. Women are still under-represented in school administration, particularly at the highest levels of responsibility. This paper presents findings of a study that examined issues for women in accessing administrative positions, acculturating into the organization, advancing on the hierarchical ladder, and advocating for other women who may follow. The results suggest that the administrative profession, including women themselves, would benefit from a more sophisticated understanding of the gender biases that still persist to keep women on the operational and cultural margins of school organizations. (Contains 1 table.)