Although the concept of leadership has been explored in the educational context, it continues to be a vague term, which most people find difficult to define. The present study offers insights into understanding how teachers' personal values (self-enhancement and self-transcendence) explain the preference for styles of effective principal. Beyond the direct effect on perceptions of the effective type of leader, we argue that values may also interact with organizational contexts in influencing perceptions. We suggest that teachers' managerial position may moderate the relationships between personal values and perception of the effective principal. Two hundred fifty-five Israeli teachers participated in this study by completing questionnaires. The questionnaires were administered using identical electronic and hard copy versions. The findings support the hypothesized effects of personal values on perceptions of the effective principal. However, hypotheses regarding the moderation effect were not supported. The study highlights the theoretical understanding of the relationship between personal values and individuals' perceptions in organizations. The present study also emphasizes the way to which individuals' cognitive structures characterize the effective leader. These findings should serve as a constructive tool for principals in choosing a leadership style that matches the teachers' values or/and in the teachers' recruitment process.