Women's participation in school administration is low and actually declining, despite legislation, affirmative action, and special programs. This article views the research guiding educational policy as useful, but concerned with ancillary issues. After a literature review of sex discrimination, administrator gender differences, role conflicts, and norms favoring men, this article addresses the informal criteria and organizational processes that favor men and hinder women. It describes a retrospective, ethnographic study of 25 women in educational administration careers. Data analysis reveals three career development stages. Women administrators begin as culturally defined, molding identities, behaviors, attitudes, and choices according to society's expectations. (In a school environment, this means women remain teachers, and administrators are male.) If women teachers develop supports and incentives, they may pass through transition (a difficult resocialization process) and eventually become self-defined, competent, and placed in higher administrative positions. Analyzing women's careers according to organizational socialization theory provides useful perspectives for rethinking assumptions and formulating new questions. Besides showing women where the informal barriers lie, this theory shows policymakers and university-based educators what structures need alteration. Appended are 34 reference notes. (HLM)