The purpose of this study was to examine the effectiveness of an Illinois metropolitan program that prepares teachers for administrative and supervisory positions in schools by analyzing, over a 10-year period, its employment outcomes. Overall, from 1995 to 2005, 503 students graduated from the program, 451 of whom with Illinois principal certificates. By Fiscal Year 2007, 168 of the certified candidates had held administrative positions in public schools in Illinois; 38 had served as principals. This rate falls short of the Illinois State Board of Education's (ISBE) 2.0 ratio of new certificates issued to new positions filled upon which educator supply and demand projections are made each year. It was recommended that the program continue strengthening practical experiences for its candidates, and expand networking relationships, not just within the city's public school system, but also with suburban school districts. Candidates will then have exposure to more prospective employers. Because of the competitive nature of the administrative sector, it was also recommended that the program work with the schools to develop mechanisms for valorizing and utilizing the leadership skills and technical competencies of the ever-increasing numbers of teachers with administrative certificates, but employed in non-administrative positions.