Although record numbers of women educators are entering masters and doctoral programs in educational administration, the percentage of women who actually obtain positions in educational administration is under 30 percent. This paper reviews the experiences of women who have obtained positions of educational leadership as reported in a number of studies, and examines the ways in which they prepared to enter and successfully entered the field of educational administration. Despite the wide availability of literature offering suggestions to aspiring women administrators and the evidence that women candidates are following the advice, there is also evidence that women are not acquiring administrative positions or are not staying in the administrative positions for long durations. It is almost as though women are doing everything right and still not succeeding. The paper cautions against falling into the following traps identified by Fine and Gordon (1989): (1) to note positive progress in relation to women's futures without sufficient cautionary analysis; (2) to psychologize structural forces that construct women's lives; and (3) to promote individualized change strategies wherein women are invited to alter some aspect of the self. Therefore, although it is important that women prepare for administrative positions by adopting suggested strategies, they also need to be aware of the structural forces that impinge upon them. (Contains 25 references.) (LMI)