The resurgence of public concern about the effectiveness of schools has brought with it a renewed appreciation of the importance of the principal in the educational process. Most preparation programs for school administrators now require some type of internship or field experience. The purpose of this study was to gain a better understanding about mentor-protege relationships and the personal and contextual factors affecting those relationships in a regional program for the preparation of principals. Mentor-protege relationships were examined through the collection and analysis of demographic data, scores on a semantic differential, scores used to measure compatibility of personality traits (FIRO-B), and in-depth interviews. The personal and professional questionnaire and semantic differential were both developed by Martha Cobble. Data for four of the six dyads in this study were collected but not analyzed by Cobble in her exploratory study describing mentor-protege relationships in a regional program for the preparation of principals. The findings of this study indicated that mentors were important to the career development of proteges in educational settings. Close personal and professional relationships developed between mentors and proteges, and both populations stressed professional aspects of their relationships over social aspects. The mentors' ability to plan meaningful activities and experiences based on their administrative experience was more important to the development of the relationships than were demographic factors such as age and gender. This study should extend the generalizability of Cobble's work and be of interest to mentors, proteges, and others wanting to learn more about mentoring in educational administration. / Ph. D.