This study examines the experiences of prominent college and university presidents recognized for leading the successful transformation of their institutions. While "change" and "transformation" are often used interchangeably, the success rate of transformation at the institutional level--of reinventing the organization based on a new model and vision for the future--has remained steady at just 30% (de Los Reyes, 2015). In order to raise the success rate, this study sought to increase understanding of key elements required to drive organizational transformation. To do so, four eminent college and university presidents were interviewed about their experiences and decision-making when leading transformation at their institutions. Analysis of transcripts and resources using integrative complexity as a theoretical framework helped identify patterns across the case studies. Seven key elements emerged as crucial for driving transformation: challenging conventions; taking bold risks; empowering others within the organization; maintaining values while charting a new trajectory; knowing the institution; designing purpose and vision; and understanding the organizational complexity and global context. The findings suggest a nuanced interplay between leaders and organizational context, as well as leaders' mindset, relationships, and decision-making. The results of this research are intended to support current and future leaders wanting to drive transformation across different sectors, to help leaders make a difference in their organizations, communities, and society. [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.]