Career opportunities for those seeking school principalships should be available if predictions are correct, yet many inexperienced principals will fail when confronted by the first challenges inherent in a position of educational leadership. This study reviews some of the major problems and issues that appear to be characteristics of the beginning years of the principalship. A series of recommendations strengthening the leadership contributions of incoming administrators are also made. The findings from intensive, indepth interviews conducted with 12 first- and second-year principals pertain to (1) role clarification problems and difficulty handling authority and responsibility; (2) technical expertise problems, both in procedural or technical expertise and in interpersonal skills; and (3) socialization to the profession and the system issues. Recommendations include (1) increasing future administrators' awareness of the fundamental features or "realities" of the principal's job; (2) providing opportunities to reflect on the actual purpose behind the skills of the job; (3) creating more specialized inservice training programs; (4) reducing feelings of isolation through a "buddy system" enabling the new principal to receive feedback; and (5) providing a more experienced principal to turn to for advice. Seventeen references and an appendix conclude the paper. (WTH)