Over the past decade, the independent school landscape in the U.S. and Hawai'i has experienced a dramatic transformation resulting in school closures, consolidations, and attempts at expansions. Leadership of organizational change, particularly within complex contexts undergoing highly dynamic and disruptive forces, is long understood as challenging at best and destructive at worst, where major organizational changes more often fail than succeed. This qualitative case study explored how independent school leaders in Hawai'i negotiated and led the process of school expansion in order to understand factors and practices that influence this organizational change. Through a cross-case analysis, this study examined the intersects of leadership approaches, organizational climate, and the operational environment at three independent schools in Hawai'i to discover rationales for school expansion and effective leadership practices to facilitate organizational change processes. The investigation explored the topic through a conceptual framework of organizational change leadership and an interpretive theoretical perspective framed by a constructivist epistemology and pragmatism. The significance of the investigation lies in the study's uncovering of the mechanisms and theories of change at three schools that deepens and enriches understanding of key contextual elements, challenges, and opportunities for independent school heads and governing boards considering school expansion. Unique circumstances and contexts of independent school expansions reflected system-level changes that were ''punctuated'' and ''continuous'' as well as ''adaptive'' and ''emergent'' to adjust to complex and unpredictable environments. The researcher purposefully focuses on effective practices and principles rather than emphasizing best practices to avoid making context free assertions and findings. [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.]