Superintendents have vast demands placed upon them by their school boards and via the political pipeline. The purpose of the study was to identify strategies/behaviors that successful superintendents used to build strong relationships and trust with their school boards within their entry period. It is during the entry period that determines whether a superintendent experiences success or failure. This study captured those strategies in order to provide a blueprint by which other superintendents, researchers, policy makers, and leadership training programs could use. This study implored the use of a qualitative approach using surveys and face-to-face interviews with superintendents across California. Nine doctoral students from the USC Rossier School of Education developed survey questions and corroborated and validated them through the conceptual frameworks of Bolman and Deal (2008), Watkins (2003), Covey (2006), and Hurley (2006). The research team sent out a total of 90 surveys to superintendents and their school board president/board member designee (as identified through the selection criteria). A total of 64 superintendents and 48 board members participated in this study with 46 matched paired surveys (superintendent and board member) returned for further case study consideration. From the aforementioned surveys, the researchers chose one superintendent and board member, respectively, to interview. These interviews provided the contextual basis by which qualitative data was obtained and triangulated to confirm the survey results. The results of this study shed light on the following questions: (1) What strategies/behaviors were successful superintendents using to build strong relationships and trust with the board during their entry period; (2) How did superintendents implement these strategies and evaluate their success; and (3) What formal/informal leadership preparation assisted superintendents for entry into the superintendency? From the survey results, the following themes emerged that successful superintendents experienced during their entry period to establish trust and a positive relationship with their school boards: (1) the use of a formal or informal superintendent entry plan during the first 90-100 days had positive benefits for new or transitioning superintendents; (2) the frequency of the communication strategies played a key role in the establishment of trust; and (3) informal administrative experiences prepared future leaders for the superintendency. [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.]