The purpose of this study is to explore the department chair role relative to challenges and breakthroughs women leaders experience both inside and outside the discipline of education. The research reported is an exploration of relatively uncharted territory, adding to the data-based studies that exist of female leadership in this post-secondary context. Incorporated into this survey-based study are constructs established in the literature around relational and organizational aspects of leadership behavior. While attention is given to gender and leadership issues reported by 121 female department chairs, the discussion is broader than gender considerations. Focus is on the major challenges that practicing leaders have encountered, particularly within the domains of administration and scholarship. Included is discussion of these leaders' initiatives, reflections, and advice, complete with verbatim quotes, thematic analyses, and relevant tables. One recommendation is that more research be conducted of the issues and work of female department chairs, with consideration of the gender dynamics involving work-role identity. Other recommendations include the advocacy of women faculty members as college-level leaders who are effectively mentored.