Educators who enter administrator/leadership preparation programmes undergo an interesting transformation. They enter as teachers, thinking as teachers do, and they graduate as future administrators, thinking as administrators do. This enhanced, school-wide perspective provides a number of benefits to the teachers themselves, to their administrators, and even to the students within the school's classrooms. This article looks at the types of individuals who enter these programmes and what motivates them. It also discusses this paradigm shift that occurs as they progress through the course work. It provides some testimony from students about their enhanced "administrative eye" and concludes with some opinions on some current trends in policy requirements that could negatively impact successful recruiting of future administrators into these programmes.