A frequently cited explanation for women's underrepresentation in educational administration is the incongruence between traditional administrative role stereotypes and gender stereotypes. However, this paper posits that certain educational and demographic trends may influence school administrator roles to become less stereotypically masculine. Simultaneously, substantial numbers of administrative openings are anticipated, and significant numbers of women are securing administrative credentials. These forces may combine to increase women's representation in school administration. This paper aims to: (1) discuss the nature of sex role stereotyping in administrator selection; (2) describe educational reform and student demographic trends that may reshape school administrators' roles; (3) describe certain demographic trends involving school personnel that may increase women's educational leadership opportunities; and (4) discuss how these trends and patterns may combine to influence greater representation of women in school administration. The 1980s educational reform movement has spawned numerous changes (including site-based management, teacher empowerment, instructional leadership, and school effectiveness efforts) that may significantly alter the image of schools and school leadership. By the late 1990s, enrollment figures for school-aged children will approximate those of the early 1970s. This trend and the problems of a changing student population suggest a need for a different type of administrator--an "instructional physician," rather than an "executive manager" or "coach." The weakening of the dissonance between administrator role stereotypes and female stereotypes at a time of increasing educational leadership opportunities should see more women in administrative positions. (35 references) (Author/MLH)