Experience with the international copying of educational policies and practices suggests that “borrowed” changes are effective only if the underlying values are congruent with the culture of the receiving society. Consequently researchers are paying more attention to cultural issues. Although there is much agreement about the desirable characteristics and behaviors of good leaders, there is little information about the relative importance of those characteristics and behaviors in different cultures. This article reports findings from an investigation of Greek and Cypriot educators’ conceptions of positive and negative characteristics of school leaders and compares them against other researchers’ findings from other countries. The findings support the proposition that preferences for leadership style are different in different regions, and illustrate the need for caution in using “recommended practices” that were developed in other contexts.