Women in education are strongly represented in the classroom but are much less likely to become school district superintendents. The purpose of this phenomenological study was to understand how women who have been superintendents for at least 3 years experienced mentoring and role preparation as they worked to attain the position. A transcendental phenomenological research methodology amplified and highlighted the voices of interviewees. Prominent themes included the glass ceiling, family influence, career pathways, mentoring and sponsorship, representation, volition, and personality characteristics. The underrepresentation of women in the superintendency is not changing quickly enough and perpetuates gender inequality in educational systems.