The purpose of this study is to examine differences in the career pathways and experience of male and female superintendents employed in Illinois. In order to achieve this overall objective, the researcher examined gender differences in the career pathways of Illinois superintendents as well as gender differences in the perceptions of superintendents regarding which position most significantly contributed to her/his perceived ability to demonstrate AASA's professional standards for superintendents. Using a convergent triangulation design, both a survey and superintendent interviews were conducted with interested unit school district superintendents currently employed in the position within the State of Illinois. The data collected via both the survey and the interviews provided the required information to answer all four research questions included in this study. Conclusions of this study include the finding that there are no predominate pathways to the Illinois superintendency, although women travel a significantly greater number of unique pathways to this leadership position. 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. While finance and human resources management were identified as areas in which students felt least prepared, there were no observed differences between the perceptions of preparedness between male and female superintendents. Recommendations for current practitioners are the following: 1) superintendent preparation programs should provide candidates with greater opportunities to build finance and human resource management skills; 2) experience is not a contributing barrier for females aspiring to the superintendency; and 3) AASA's professional standards for superintendents continue to be a relevant tool for superintendent evaluation as well as professional reflection. Further, recommendations for future research include: 1) career pathway and AASA professional standard correlations should be conducted in other states; 2) the principalship should be investigated further with particular emphasis on the responsibilities and roles of this leadership position; and 3) mentoring, especially a comparison of that which occurs prior to and after obtaining a candidate's first superintendency should be gathered in order to address this barrier. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]