The university president's role can be complicated and ambiguous. The pathway to the presidency remains a mystery as traditional and non-traditional presidents approach the position with various experiences, and 75% of those hired arrive as first-time presidents (Gagliardi et al., 2017). New and aspiring university presidents would benefit from learning how other presidents arrived at their positions and how their preparations impacted their ability to navigate their presidencies. Tailored training programs within specific fields such as student affairs or academic affairs exist; however, a better understanding of the impact of preparation for the presidency addresses the gaps in the existing literature on how presidents understand the role and their experiences held as they moved into that role. This qualitative collective case study used naturalistic inquiry to understand the participants' voices as they explain the role of the president, background experiences, and preparedness. Fifteen participants, eleven classified as ascending through the traditional path while four arrived through non-traditional routes, offered their stories. By showcasing the perspectives of traditional and non-traditional presidents, research regarding the path to university president becomes less mysterious. Findings from traditional presidents showed that: (a) presidents perceived themselves to be ambassadors of the university, (b) presidents found the importance of incorporating mentors as part of the preparation for the presidency, and (c) presidents must be authentic and commit to their institutions. Non-traditional presidents explained that: (a) they believed they were the face of the university, (b) their experiences were supported by being practitioners, and (c) presidents must incorporate challenging initiatives. From these findings, the researcher established presidents agree that preparation for the presidency consists of: (a) collection of experiences, both educational and professional, (b) an effective team to support the president, (c) strong support system such as family, friends, colleagues, and other presidents, and (d) network among presidents, industry leaders, and alumni. This research addresses the gap in existing literature on how university presidents ascend to the role, and the benefits of traversing these different paths. The researcher included recommendations for aspiring presidents, search committees, and search firm consultants relevant to preparing and educating university presidents. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]