The effect of leadership styles of school administrators on teacher evaluations of their job performances is examined in this paper. A secondary focus is a comparison of teacher characteristics and their effects on administrator evaluation. A principal evaluation survey was administered to 120 Chicago public and nonpublic school teachers, counselors, coordinators, and assistant principals with ratings assigned on the basis of four leadership styles: Laissez Faire, Democratic, Dictatorial, and Transactional. Findings indicate that teacher experience or principals' administrative level had no significant effects on evaluation. Overall, the Transactional and Democratic leadership styles as well as the type of school (private and preschool) had the most positive influence on the evaluation of principals' job performance. The results suggest that principals, particularly those who employ the Laissaz Faire and Dictatorial styles, reexamine their approaches to school management. Five statistical tables and an extensive bibliography are included. (LMI)