The issue for this case study involves current administrators' views regarding how well prepared they felt for their school leadership positions after graduating from an educational leadership program in Florida. The author examines whether the courses that perspective school administrators are required to take during their graduate program prepare them to be effective leaders. For this case study, the author relied on two sources of information from an elementary school in Florida. Vanessa, a second-year principal, and Patty, a first-year assistant principal, were the author's primary contacts. (Fictional names only are used in this text.) During a series of personal interviews in June 2001, the author asked both women leaders the same three questions: "What do you think are important leadership characteristics of a school administrator? What might you have been unprepared for during your first year of administration? What do you think colleges could do to help future leaders become better prepared?" From the author's interviews with Patty and Vanessa, she learned that they felt the universities they attended had successfully enabled them to enter the administrative world in terms of being prepared to take the Florida Educational Leadership Exam (FELE). The FELE is an official gateway to school administration, as candidates seeking certification in educational leadership are required by the Florida State Board of Education to take this examination. However, both of the author's participants in this case study stressed that experience and advice from a mentor/coach was what filled them with the confidence and cultural knowledge they needed to perform their jobs successfully.