The purpose of this multi-case study was to explore the experiences of college presidents who have held top executive level positions at both academic and corporate institutions and who ascended to their college presidency from a role outside higher education. Through this study, the researcher ascertained from the presidents how prepared they believed they were to assume the role of president and uncovered what these particular leaders perceived as the similarities and differences in leading a college and a corporation. Seven presidents from colleges and universities in New England participated in this study. All of the presidents interviewed indicated that they felt prepared to assume the role of president from their former leadership position outside higher education. They described two main areas of preparedness: their own prior engagement in higher education and the match of their strengths to the needs of the institution. The similarities and differences described by the presidents were in the areas of finances, faculty and outcomes. The presidents spoke specifically about the attributes of professionals they believed would be successful in making a transition from a corporate environment to higher education, which included being open-minded, being collaborative, and having a passion for the mission. The results of this study may benefit Board of Trustees who are considering non-academic candidates for the role of president and current corporate CEOs who are considering transitioning to a leadership position in higher education.