This paper focuses on certain aspects of superintendency in Finland and Sweden, neighboring countries with a shared history, similar Nordic cultural beliefs and political systems. Our research question is: What does a knowledgeable superintendent know? By using this particular wording, we intend to probe deeper into what more experienced superintendents consider to be essential knowledge as an outcome of what they have learned over their years in service. Thus, we aim to go beyond technical rationality and approach what one might consider as profound professional judgment (Bondi 2011; Hargreaves 2018). Research into this issue has been insufficiently highlighted in the field of educational leadership, and as such, this paper is consistent with the theme of the 2020 UCEA.