Although developing leadership is often acknowledged as an important topic in higher education today, the percentage of women found in high leadership positions still remains quite low. Since the 1970s significant efforts have been made to increase women's participation in higher education administration, with some progress, according to Glazer-Raymo (1999). Today more women are interested in leadership. Yet the leadership gap continues and opportunities for in-depth development are still not widely available for many women. Little has been published about how high-level women leaders actually developed the leadership knowledge, skills, and abilities necessary to successfully lead. In addition, according to Olsson and Pringle (2004), "much of the women in management literature has focused on the glass half empty" and the perceptions and experiences of women who may be constructed as victims of organizational structure and culture that privilege masculine characteristics. They explained that the literature is missing studies of women who have succeeded and may feel comfortable participating in such a culture. The purpose of this article is to do just that. It reports the results of a research project studying successful women leaders who feel comfortable in an often male-dominated culture. It was designed to hear the voices of women leaders in higher education and highlight their perspectives and developmental experiences.