This study aims to explore the frequency and extent of principals’ use of systems thinking activities in Israel; to examine whether principals’ gender and seniority predict their systems thinking activities; and to determine how systems thinking activities are related to school outcomes. Results indicated that principals’ seniority predicted their extent of systems thinking, but no differences were found within principals’ gender. Positive correlations between principals’ systems thinking and middle-leaders’ job satisfaction and organizational commitment were found. Implications for theory, practice, as well as future research, are discussed.