This paper describes a study that involved 25 school administrators who participated in one of five administrator-preparation programs at four New England universities. The study examined participants' perceptions of job preparedness and the ways in which components of formal training programs (internships, mentoring relationships, reflective practice, and student cohorts) prepared school leaders for their jobs. Data were gathered from interviews with the 25 administrators, analysis of school documents, and a survey of 627 administrators, teachers, and supervisors at each of the administrator's schools. The survey elicited 394 responses, an overall 63 percent response rate. The findings include discussion about the advantages and disadvantages of student cohorts, the key role of reflection within a program, the authenticity and connectedness provided by internships, and the importance of mentoring relationships. Suggestions for improving administrative training are: (1) include students with varied experiences from nontraditional backgrounds; (2) design programs that foster learning and provide a supportive environment for adults, such as cohorts and mentoring; and (3) implement learning practices and an integrated curriculum that reflect work-place problems and promote the development of problem-solving skills and reflective practice. One table is included. (Contains 55 references.) (LMI)