The relationship between specific character traits and leadership has long been a focus in research. Grit, as a trait, has been explored in many realms such as the military, extremely tough competitions, relationships, and education. While there are ample studies that have examined grit in relation to successfully overcoming difficult situations and enduring in challenging jobs, there is little research focusing on grit as it relates to the role of superintendent. The job of superintendent is a complex one, comprised of a wide range of responsibilities. It is often filled with demanding challenges, difficult obstacles, and frequent turnover. This qualitative research study investigated the perceptions of superintendents on grit and its relationship to tenure length. This study analyzed the views and experiences shared by superintendents who had been serving their districts for longer than average tenures and had grit levels in the high and extremely high ranges. Results from this research indicated a positive relationship between grit levels and superintendent tenure lengths. Additionally, the findings point to the ability for grit to expand as challenges are successfully met. The results lead to specific recommendations for current and aspiring superintendents, school boards, and superintendent preparation programs. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]