This study utilized a qualitative approach to focus on three essential elements: how superintendents are prepared to serve in their role as school district leaders, how they are recruited, and what support is available to help them succeed and remain in their position. The study explored these essential elements from the perspective of currently serving urban and suburban superintendents, board members, and an executive search consultant within the state of California. The research questions used to guide this study were as follows: 1. How have training programs and experience prepared superintendents to manage the complexities and challenges of the superintendency? 2. What are the perceptions of current successful superintendents and school boards regarding the strategies used to help the current superintendent to attain his or her current position? 3. What are the perceived strategies that support the retention of superintendents? Structured interviews were conducted with nine participants (five superintendents--two from suburban school districts and three from urban school districts, three school board members, and an executive search consultant). The interviews were guided by a list of 13 questions that focused on training programs, prior experience, career pathways, and relational supports that helped to prepare superintendents and support their retention. Quantitative data were also collected to support the emerging themes derived from the qualitative findings. School district superintendents who were members of the Association of California School Administrators and the Dean's Superintendents Advisory Group received an invitation and link to the online survey. School board members who were affiliated with the California School Boards Association also received an invitation to the online survey. The results of this study revealed the following: 1. Superintendents' prior work experiences, mentoring support, and various career paths prepared them for the superintendency; 2. Strategic professional relationships with mentors, informal and formal networks, and creating an entry plan were important strategies that helped superintendents attain their position; and 3. Board relations, having a strategic plan, and establishing and maintaining trusting relationships were important to the retention of superintendents. [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.]