Aware of the gender disparities that exist in the most coveted school district leadership positions, the researchers undertook the project reported here to uncover themes related to factors that contribute to the low numbers of women in the superintendency and assistant superintendency. Having knowledge and understanding of the factors that contribute to the dearth of women's voices and viewing this knowledge from a feminist framework helped us to understand how gender has played into assumptions and practices related to the superintendency and assistant superintendency. Readers can learn from the stories and experiences of the women reported here and understand practices that serve to block women from becoming educational leaders while also learning how to make the paths to leadership taken by a future generation of women leaders less problematic through suggested actions and strategies.