A standard quantitative design study employing three surveys was used to identify motivating factors leading district level licensed personnel to choose whether or not to apply for the superintendency. Motivational theory, including the subcategories of content, process and environment, served as the framework for identifying features of district level positions that are, for qualified individuals, motivating or not motivating in their decision to apply for district level administration including the superintendency. A three-part survey was given to examine three areas of motivation: a) What motivates a person to become a superintendent; b) What does the person like about the superintendency; c) What are the challenges of the position. Data were analyzed using ANOVA and a MANOVA. Results indicated that there were no differences between superintendents and non-superintendents for the motivation for the job. Data showed gender differences suggesting that females like the position better than males. There was also a three-way interaction for position, gender and district size. Challenges were divided into four subcategories, with significant differences between superintendents and non-superintendents on organizational challenges and student-related challenges. Implications and further study are discussed.