Administrators draw on prior experiences when negotiating, implementing new curricula, and resolving conflicts. This study attempted to determine whether building level administrators included graduate study, union leadership roles, coaching experiences, and school committee leadership as part of their career development prior to assuming educational leadership roles. The study also investigated possible male-female differences, such as total number of years as teachers and/or administrators, training choices, and ratings of administrative preparation experiences. A field-tested questionnaire was sent to 218 randomly selected elementary, junior high, and high school principals in southeastern Michigan districts with a school population between 2,400 and 30,000 students. Responses were received from 190 (87 percent) of the total group, including 128 male principals (67 percent) and 62 females (33 percent). Findings showed that female principals, compared with males, enter their roles with more teaching experience and more school committee leadership experience as teachers, but with less experience in other work-related settings that might enhance and hone their leadership skills, such as noneducation union membership and athletic coaching. The women surveyed moved out of their teaching districts to obtain their administrative positions and spent fewer years as administrators. The men were more likely to be principals where they had taught and to have been in administrative roles longer. All respondents attached a high degree of importance to advanced degree work. Appendices contain a sample questionnaire and summary data tables. (13 references) (MLH)