The purpose of this research study was to compare male and female assistant superintendents and their descriptions of Internal Barriers, External Barriers, Internal Motivators, External Motivators, Stressors, and Discriminatory Acts they anticipated encountering on the route to the superintendency in Suffolk and Nassau Counties on Long Island, New York and in Westchester County, New York. Furthermore, the purpose of this study was to determine if their experiences of Internal Barriers, External Barriers, Internal Motivators, External Motivators, Stressors, and Discriminatory Acts influenced their willingness to pursue a position as superintendent of schools. Data were collected using a 68-item survey that was developed based on the state of the American school superintendency. The survey aligned with the American Association of School Administrators (AASA) ongoing 10-year studies. One hundred forty-nine, or 74.5 percent of the 200 surveys, were returned. Overall, the findings of the study suggested that assistant superintendents viewed the superintendency as a complex position that was not appealing to them. Male respondents were more willing to pursue the superintendency than female respondents were. [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/en-US/products/dissertations/individuals.shtml.]