Understanding antecedents to superintendent leadership development is crucial for the continued improvement of schools. This qualitative study seeks to identify skills superintendents consider critical to their position, antecedents that developed those skills, and provide an increased understanding of the methods needed for developing current and future leaders. Leadership skills explored include: communication, listening, building relationships, collaboration, work ethic, thinking and processing data, empathy, integrity, instructional leadership, vision, organization, financial analysis, aptitude, flexibility, and systems thinking. This study explores common antecedents to adult learning including experience, leadership experience, reflective practice and mentorship. For this study, the adult learning theories of Skills Approach Model (Katz, 1955), Knowles' Andragogy (Knowles, Holton, & Swanson, 1998), and Kegan's Constructive-developmental theory model (Helsing, Drago-Severson, & Kegan, 2003) provided a framework for understanding common antecedents. Superintendent skills and the corresponding antecedents were also compared to the leadership theories of Transformational, Synergistic, Adaptive and Instructional Leadership, as well as Marzano and Waters (2009) five skills for district leadership success. The methodology used online surveys, as well as purposeful interviews of current superintendents in Oregon. Findings include identifying skills needed in the superintendency and antecedents toward skill development. Implications include identifying skills needing further improvement and barriers to increasing skills, recognizing the need to raise awareness of common antecedents to skill development. [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/en-US/products/dissertations/individuals.shtml.]