Being a skillful school leader presumes the competence to judge the ethical consequences of actions. This implies a need for all school agents to discover and analyze what values are at stake and, in turn, reconcile didactic rationality with ethical rationality. This article aims to explore ethical dilemmas in daily school practice, experienced and identified by school agents on different levels: school politicians, superintendents, principals and teachers. These dilemmas are further analyzed from different ethical perspectives. The findings demonstrate a variety of ethical dilemmas on different leadership level. What was considered as an ethical dilemma on one level is not mentioned on another level in the school system. Nevertheless, one common trend was the conflict between a strong values oriented profession and personal values of individuals, where children's rights might be at stake. (Contains 1 note.)