The purpose of this qualitative study was to examine the relationship between the background of superintendents and their hiring of principals. This study explored whether six superintendents in Nassau County, NY hire principals based on what the research says makes a successful principal or based on their personal background and professional experiences. Using a narrative inquiry approach, the researcher analyzed interviews with six superintendents, their resumes, and documents used for hiring 19 principals. The study found that superintendents' backgrounds and experiences influence the hiring process of principals while also seeking school leadership practices and personal qualities found in the research. Each of the participants has become superintendent through different career paths and what they look for in principals has similarities and differences. This study will inform superintendent preparation programs about the relationship between prior experiences and how superintendents select new principals. In addition, aspiring superintendents will learn about the possible effect of certain pathways to becoming a superintendent. Lastly, current superintendents will become more aware of how their backgrounds may be influencing how they select new principals. [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.]