This qualitative research examined perceptions of Muslim and Jewish teachers in Israel concerning the masculinity of male school principals, and the way in which these perceptions affect principal–teacher relationships. Muslim and Jewish teachers studying for master of arts’ degrees in a university and a teacher-education college in Israel completed open questionnaires and participated in semi-structured interviews. Findings indicated similarities and differences between the perceptions of the two different cultural groups, highlighting reciprocal principal–teacher influences and elucidating a cultural discourse concerning a principal’s perceived masculinity and femininity. It is concluded that the concept of the school principal’s masculinity is a fluid social construct, varying according to cultural–ideological perceptions that affect the principal’s own preferred communication patterns in the school. Since both masculine and feminine qualities are needed for effective education leadership, a policy advocating employment of female mentors for newly appointed principals, in order to give voice to female qualities in principalship, is strongly recommended.