Despite the almost equal proportion of females to males who receive doctoral degrees in the U.S., women remain underrepresented in senior positions--faculty and administrative--in institutions of higher education. Unlike the more blatant discrimination extant before the era of civil rights legislation, barriers today are less obvious to the untutored observer. This paper will explore the gendered schemas that impede the equitable representation of women in senior administrative roles in higher education. Current formulations suggest a variety of rationales for this underrepresentation, including: traditional devaluation of women's abilities; beliefs about the appropriateness of roles and behaviors for women; unconscious biases which disadvantage women in multiple settings despite evidence of success; failure to appreciate the precedents provided by women administrators who created pathways for contemporary women in administration; as well as the reluctance to reconsider the requisite skill sets for a successful institutional leader in the 21st century. A consideration of leadership theory and research on the impact of stereotypes suggests ways in which women can develop the resilience necessary to challenge the traditions of the academy, traditions which remain heavily reliant on dated beliefs of male superiority and the rightness of the majority culture.