There is a growing trend of individuals coming to the university presidency from nontraditional/nonacademic pathways. However, current dialogue on the topic seems to be focused on the opinions or preferences associated with certain presidential career patterns or pathways with little emphasis being placed on what truly prepares individuals for leading institutions of higher education in the 21st century. Therefore, the purpose of this study was to explore the preparatory (pre-presidential) experiences of university presidents, and their perceptions about what best prepared them for the demands they experience leading today's institutions of higher education. This case study of six presidents at master's colleges and universities in the Midwest resulted in three findings. The first finding documented the importance of know-why competencies: Preparatory experiences that enculturated individuals to the understood values and perceived purpose of the Academe were critical to their abilities to successfully navigate the academic cultures of their respective institutions. The second finding documented the importance of know-how competencies: Experiences that helped individuals develop knowledge and expertise for specific job functions or duties were important preparation for the presidency. The third finding documented the importance of know-who competencies: Experiences that fostered opportunities for individuals to develop interpersonal skill sets and to learn to navigate social networks were essential preparation for the university presidency. Therefore, this study transitions discussion on presidential preparation from a pathway based perspective to a competency based perspective. [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.]