The role of a school district superintendent demands a balance of professional leadership and political astuteness. Individuals in this role possess distinct skills, values, and beliefs essential for navigating its complexities. This mixed-method phenomenological study employs self-reported values, decision-making styles, and interviews to explore the superintendent's experiences. Utilizing qualitative and quantitative data, this study delves into the intricate dynamics of value-based decision-making by school district superintendents, highlighting the pivotal collaboration between personal and institutional values. A phenomenological mixed-methods approach offers an understanding of how superintendents develop values, come to be in their positions and utilize their experiences to inform value-driven decisions, focusing on the role of collaboration in this process. By synthesizing qualitative and quantitative findings, this research contributes to the educational leadership and decision-making literature, illuminating the nuanced interplay between values, collaboration, and decision outcomes within the realm of school superintendency. Key findings are how reliant superintendents are on their values, how the years serving in their roles affect their willingness to adapt and compromise, and how cultural contexts and knowledge of their community help leaders navigate conflict. [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.]