The purpose of this study was to learn about mentoring relationships in a principal preparation program, the contexts in which they developed, and the influence of personality traits on relationships. Relationships between four pairs of mentors and proteges were described using data collected with a questionnaire, a semantic differential, the FIRO-B (Fundamental Interpersonal Relations Orientation), and in-depth interviews. Analyses of data identified variables associated with mentor-protege relationships and their influence on relationships. The variables that played a role in the formation of relationships were age, gender, experience, proximity, school division support, program design, time, and family support. The semantic differential proved to be an indicator of relationships while FIRO-B was inconclusive. This study should be beneficial to mentors, proteges, and others interested in learning more about mentoring relationships in educational administration. / Ed. D.