This study explored the relationship between a superintendent's leadership style and their strategic planning and change management process using a qualitative methodology with a case study design. Purposeful sampling methods were used to identify 13 superintendents from the Southwest and Midwest regions of the United States. The participants were interviewed using a semi-structured interview process. Findings suggested that superintendents define what they mean by strategic planning as well as how they measure success for their strategic planning efforts. Additionally, it was found that leadership preparation to manage and support change efforts needed to be improved. These findings led to the conclusion that the contextual, cultural and situational factors lead superintendents to find ways to integrate their experience with these district factors to define both strategic planning and assessment. The factors that impact a leader's experience are often embedded in the work they have done and not in leadership development programs. Implications for practice include the use of a mixed method strategic planning model that includes structural components of traditional models, but allows for flexibility to address contextual, cultural and situational factors in a district, and the embedding of scenario-based modules related to planning and supporting change efforts into leadership development courses at universities and external leadership development programs. [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.]