This article discusses the lack of female teachers in leadership positions. In 1988, The National Association of Elementary School Principals (NAESP) and the National Association of Secondary School Principals (NASSP) commissioned a study to address the administrator shortage. They found that the top three reasons candidates gave for not applying for principal openings were low pay in comparison to the job responsibilities, too much stress, and too great a time commitment. However, these results fall short of explaining why 75 percent of women hold jobs as teachers in public education while men hold 60 percent of the administrative positions (National Center for Education Statistics 1997). This discrepancy suggests that despite female interest in education, women have trouble making the leap into administration, wasting a great deal of female talent. This article evaluates the role of female administrators, encouraging factors, and inhibiting factors.