Physician assistant (PA) education has lacked literature that looks at the issue of leadership development, particularly of program directors, yet as the profession has grown it has often struggled to identify qualified leaders for directors of physician assistant training programs. There are currently 149 accredited programs throughout the United States and each program is required by the accrediting body to have a full-time program director, but it is not known what common paths these directors have taken to assuming the role of leader, nor do we fully know which paths to leadership provides directors with the optimum opportunity for comfort or preparedness in these positions. The purpose of this study was to determine the career paths of program directors in physician assistant education and to further determine if there is a specific path that provides the optimal start to this position in terms of comfort or preparedness across specific areas of administration. A quantitative approach was taken utilizing a survey methodology to determine what the common pathways to leadership were for current PA program directors. The study found that a variety of career paths are taken by program directors prior to their appointment as a program leader, but the only aspect of their background that may predict the best level of comfort or preparedness for the position is their age at the time of their appointment. Pearson’s point-biserial correlation indicated a significant positive relationship between the age of the program director at the time of their first appointment to their position and their total comfort score across areas of administration (r = 0.315, p = 0.005, N = 79). The study discusses the limitations of its findings for understanding the role that age or any other factor plays in predicting success as a program director.