While responding to increasing calls for accountability, educational leaders are challenged continually by a myriad of complex tasks amidst the need to adapt their postsecondary institutions for responding to the changing needs of society. This review of literature examines comparisons between the leadership style of Charles William Eliot and the prescribed theories introduced in current literature and textbooks. More specifically, it includes treatment of the leadership theories used, organizational environments, and the mindset and actions of followers.