Mentoring is a widely used method of induction into a variety of professional roles, including educational leadership. However, little scholarly literature has focused on the role of mentoring in the career development of special education administrators. In this examination of 14 such mentoring relationships, the existence of career and psychosocial functions as theorized by Kram is explored and the perceived value of the functions to mentors and protégés in the career development of beginning special education administrators is identified. Evidence of coaching, a career function, and counseling, a psychosocial function, was found in all relationships studied and these two functions were ranked as most important to the career development of beginning special education administrators by both mentors and protégés. Recommendations include incorporating mentoring functions into mentor and protégé training to increase the positive effect of mentoring on the career development of beginning special education administrators.