Turnover of public school superintendents can be both costly and counterproductive for school districts. For those who are successful, who remain in one district as superintendent, and receive contract renewals from their school boards, it is important to uncover what may impact that success. Measures of personality have been applied to the fields of business and military to make attempts at predicting success within leadership roles. This study examines the personalities of several successful superintendents and the potential impacts of their personalities on their success within their respective school districts. In order to achieve this, we engaged the participation of nine public school superintendents from school districts throughout California. These superintendents completed DISC Personality Assessments before meeting for one-on-one semi-structured interviews to investigate their perceptions of their own personalities, the results of their DISC Assessments, their working relationships with school board members, and how personality has or has not impacted their interactions and conflict resolution with their school boards. Our results demonstrated that there is no single personality type or style that makes a successful superintendent and that successful superintendents have the ability to build relational trust, provide board education opportunities, see the influence of their experience impacting success, as well as their adaptability and capability to adjust personality to meet the needs of their boards. The results of this study underscore the need for further education in Educational Leadership programs on personality, emotional intelligence, and adaptability. This support should better prepare superintendents as they enter into these critical roles of district leadership for successful working relationships with board members and improve overall success rates for incoming district leaders. [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.]