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This study examined differences in the career pathways and experience of male and female superintendents employed in Illinois. A convergent triangulation design was employed to review the results of surveys and interviews conducted with Illinois superintendents. Results of the study included the finding that that there are no predominate pathways to the Illinois superintendency, although women travel a significantly greater number of unique pathways. Further, the teacher and principal positions were most consistently selected by superintendents as the positions which best prepared them to demonstrate AASA’s professional standards for superintendents. Finance and human resources management were identified as areas in which students felt least prepared, and there were no observed differences between the perceived preparedness between male and female superintendents.