This paper examines how superintendents and school principals enact national policy reform expectations and what characterises their local organisational arrangements. Furthermore, the paper investigates how superintendents and school principals deal with tensions as entrepreneurs. The study builds on qualitative interview data from two municipalities in Norway. Analytically, the study draws on institutional theory, more specifically, on entrepreneurship, which to a limited degree has been applied in educational and empirical studies. The superintendents and principals interviewed referred to various local arrangements and resources that were partly adapted and changed through reform work to better fit local needs. Such arrangements included intra and interorganisational dependency and cooperation with several actors and organisational resources. Superintendents and principals seemed to partly break away from existing patterns of interaction. The entrepreneurial work entailed dealing with several tensions emerging within and across institutional boundaries in the process of enacting national reform policies.