In this article, David Watson debates the pros and cons of leadership skills in both a small and large university. Watson relates his own experiences regarding the changing atmosphere of leadership. He states that his experiences have caused him to reflect on what is genuinely generic about individual capacities for institutional leadership: that the knowledge and skills needed in earlier stages of one's career may be just as important as ones gained as career changes occur. Watson in hindsight asks--Are transfers just a case of changing teams and playing the same? More critically, how easy is it to reconstruct authentic institutional leadership in a new context? Perhaps size does matter after all.