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This dissertation examined the experiences and connections between head of school leadership and culture in small, independent boarding schools in New England. This study was the result of the participation of eight heads of school from eight separate institutions, engaging in semi-structured interviews. All of the schools were secular in their practice, all-gender, and had a formal dormitory-based boarding program. Each school enrolled 400 or fewer students, focusing the impact of these leaders on a tighter, interactional lens. This study explored a relatively under-researched area of K-12 education and used exploratory, qualitative methods to gather the stories of these formal leaders. The geographic boundaries of this study were limited to the six New England states. As a result of this study, several key themes involved in the practice of leadership and cultural development arose through the conversations with these heads. [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.]