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As of May 1997, 28.8 percent of the heads of schools in the National Association of Independent Schools were female. The number grew .8 percent during the previous year and has grown at a rate of 1 percent a year for the past 10 years. This document reports the findings of a research project that explored reasons for the dearth of women heads of independent schools. The paper identifies differences in the ways in which male and female administrators and heads of NAIS schools view the job and their career-development strategies that led toward the headship. The paper identifies the barriers perceived by both men and women and offers advice from female heads of schools for overcoming those barriers. Data were obtained through a survey of male and female heads and administrators of NAIS schools, which elicited an overall response rate of 53 percent (n=106). Followup interviews were conducted by telephone with 11 survey respondents and in person with 27 respondents. Both men and women heads attributed the lack of female heads in NAIS schools to women choosing family over career and to social biases against women leaders. Women reported that women self-select out of the process because they make personal sacrifices, give up relationships, and fear the consequences for choosing nontraditional gender roles. Women heads offer the following advice to other women: Make a conscious decision to go for it; find your own leadership style; try not to take anything personally; trust your inner voice; build your own support network; insist on having household support; build a strong relationship with your board; find a good mentor; develop a strong inner life; and find a balance between work and personal life. Nineteen charts, a copy of the questionnaire, and an annotated bibliography of 59 entries. (Contains 31 references.) (LMI)