In 2014, statisticians at the Bureau of Labor Statistics found that women constitute 45% of the workforce. Women's participation in high-level organizational leadership roles remains low. In higher education, women's representation in top-ranking leadership roles is less than one-third at colleges and universities. The conceptual framework for this study was the role congruity theory of prejudice toward female leaders. The specific problem is how stereotypical views of female behavior affect women who aspire to high-ranking leadership roles in higher education. This was a qualitative study using a multiple-case study methodology. The study was organized by research questions that reflected on the underrepresentation of women leadership roles in higher education. Members of Arizona Women in Higher Education were invited to participate in interviews regarding their experiences as a woman in leadership. The interview questions consisted of open-ended questions that explored the definitions of leadership, leadership styles, how these definitions influenced their workplace behavior, and the experiences of these women in their leadership roles. The findings of this study did not fully support that the lack of women in leadership positions in higher education is due to a bias toward their role as a female when serving in the position of a traditionally defined masculine role of leadership. The conclusion is that stereotypical views of female behavior had little impact on the successful careers of the participants. The participants gave little significance to experiences with social role expectations or to the definitions society have given to the definition and characteristics of leadership. The participants' perception of their success was due to merit; the recognition by others as having the qualities and skills to lead in a variety of positions. Further qualitative research with male leaders as participants would provide a comparison between male and female gender roles and how those roles are influenced by society's expectations. Additional research using a mixed methodology may provide a broader range of understanding of women's experiences with the stereotyping of female behavior through the combining of quantitative and qualitative data analysis, as the qualitative data can enhance the interpretation of the quantitative data collected. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]