This paper focuses on fundamental aspects of superintendency in Finland and Sweden, neighboring countries with a shared history, similar Nordic cultural beliefs and political systems. We investigate what more experienced superintendents consider to be essential knowledge as an outcome of what they have learned over their years in service. From what positions about truth do they orient themselves and make decisions concerning education? Thus, we aim to go beyond technical rationality and approach aspects of the basis of professional values. We conclude that superintendent’s professional landscape emerges in the cross- section of the four different sets of relationships, where loyalty, solidarity, faithfulness, and authenticity are at stake.