The present study aimed to trace the ways by which Israeli principals manage their emotions at work and posed two questions: (1) How do principals tend to express empathy toward others in the school? and (2) How do principals regulate their empathy at work? Based on semi-structured interviews with 10 Israeli school principals, it was found that they are allowed, even encouraged, to display, under specific circumstances, three components of empathy: cognitive, affective (e.g., compassion), and behavioral (e.g., caring), while consciously inhibiting the expression of anger and fear publically. In addition, the principals use four strategies to regulate the components of empathy and its related emotions. Cultural, professional, and personal characteristics seem to explain empathy display and regulation among the Israeli principals.