The purpose of this study was to identify strategies and behaviors that successful superintendents used to build strong relationships and trust with their boards within their entry period. The three research questions were developed to guide this study: 1. What strategies and 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? 3. What formal and informal leadership preparation assisted superintendents for entry into the superintendency? This study was conducted by a cohort of researchers from the Rossier School of Education at the University of Southern California. A qualitative approach, using surveys and in-depth interviews, was used in the collection and analysis of the research data. Data analysis revealed that most successful superintendents had an entry plan and used multiple methods of communication to establish trust. Additionally, successful superintendents were strategic in their use of leadership strategies to establish a strong relationship with their board and relied on self-evaluation and self-reflection to evaluate their success as superintendents. Lastly, prior experiences, interpersonal skills, and trustworthiness were identified as factors for success. This study validated the importance and implications for aspiring and/or transitioning superintendents to understand that the entry period is a challenging and critical time. A successful transition during the entry period is possible through building trust and a strong relationship with the board. This study also provided insight for university program developers interested in creating a strong superintendent preparation program. It was found that superintendents regarded their informal training to be more beneficial than their formal training. Additionally, this study showed strong evidence of the use of business leadership strategies by superintendent participants. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]