Although women comprise about 65% of the educational workforce, they occupy only about 14% of the superintendent positions nationwide. In the past, some theorists accounted for the underrepresentation of women by claiming that women were not assertive enough, didn't want the power, lacked self-confidence, didn't aspire to line positions, were unwilling to play the game, and wouldn't apply for the jobs. Others maintained that members of educational organizations erected barriers limiting the career opportunities for women and, consequently, locked them into low level jobs. A more recent explanation purports that multiple variables such as individual agency, educational structures, professional norms, and the larger sociocultural context converge to perpetuate the demographic profile of the superintendent as male. The explanation of concern for this article is whether women, as potential applicants for the superintendency, are likely to self-select out of the process when recruitment-message content emphasizes roles often associated with men. Recent research suggests that incompatibility between the historical expectations for superintendents and the historical expectations for women may, at least partially, explain why women have yet to access the superintendency in proportion to their numbers in education. Compared to male superintendents, female superintendents have more experience as classroom teachers, are more likely to begin their administrative careers in elementary positions, and are more likely to be hired as instructional leaders. The results of studies examining the recruitment and selection of principals indicate how preconceived notions of what men and women can and ought to do influences who gets hired as principal of an elementary, middle, or high school. The author contends that organizational representatives desiring to avoid recruitment practices perpetuating the notion that the superintendent's position is "male" would do well to emphasize all major roles of the job in recruitment message content and to place value on a broader array of experiences. Emphasizing all major roles assures that recruitment-message content does not focus exclusively on attributes of the job likely to appeal to either men or women. Placing value on a broader array of experiences such as leadership as a district-level curriculum specialist may encourage more women to apply for position vacancies.