The position of public school superintendent has experienced both a redefinition and a rebirth in its criticality. With increased accountability due to the shifting public school "Back to Basics" educational perspective in the 1980s, the launch of the No Child Left Behind Act (NCLB) in 2001, and the signing of the Every Student Succeeds Act (ESSA) in 2015 by President Barack Obama, the role of superintendent has seen a shift from that of an organizational manager to that of an instructional leader. Much has been studied about the importance of the public school superintendent, particularly the challenge of superintendent retention. High turnover rates appear to contribute to the lack of continuity required to move an educational organization in the direction of its mission. One factor accounting for high turnover appears to be some superintendents' inability to build relationships with their school boards. This multi-case study/cross-case analysis examined why superintendents struggle to create and sustain significant relationships with their school boards. It explored the metacognitive processes of two superintendents, what factors contribute to their use of specific strategies, and how decisions relating to the strategies have been made. This study provides an important investigation into a topic that may offer greater understanding of ways to improve superintendency tenure, and how educational preparation and training programs for superintendents can be improved to equip superintendents with leadership skills to work collaboratively and constructively with school boards. Chief findings showed how the two superintendents in the study used strategies of relationships, management of ego, communication, educating the board, and politics to build and maintain relationships with their school board members. While the findings show these superintendents were mindful, thoughtful, and strategic, the data also indicate a linear, technical, and interpersonal connection between these superintendents' leadership and their board member relationships. The findings suggest ways to enhance superintendent leadership by having them focus on transformational leadership, adaptive leadership, and interactions with board members that affect the organizational system as a whole. Each of these is influenced by both superintendent and board member contextual understanding, political interplay, and organizational learning. DEDICATION While this journey was not without great sacrifices made by so many, this dissertation is dedicated to my father, the late Warren Lavoy Jackson. In his short 44year life, he instilled respect, integrity, honor, and perseverance. All are qualities that have lived throughout this process. His guidance and wisdom will forever live in my heart and certainly in my mind. Without his insistence that every journey deserves "completion to the end," this certainly would not have been possible. Dad, I thank you from the bottom of my heart, and this is a testament to your life of courage and perseverance. There were man...