Caught in the crossfire of expectations of improving students’ learning outcomes while simultaneously safeguarding students’ well-being, school principals must balance accountability and professional autonomy. This article presents findings from a small case study that examined the relationship between the supervisor and four school principals in a Swedish municipality. Drawing on an institutional perspective, the purpose of the study was to examine how the superintendent manages the principals through the quality assessment system through regulative, normative, and cognitive elements and how the principals relate to these institutional aspects. The empirical data was collected by interviews. Scott’s pillars of institutional order were applied to analyze what regulations, normative expectations, and cognitive elements that could be identified in the empirical material. Bridging and buffering were used as analytical tools to analyze the strategies used by the principals to relate to these institutional aspects. The findings indicate clear and well-implemented regulative routines, but also monitoring and a range of sanctions where the principals do not meet expectations. There are examples of normative elements emphasized by the superintendent, as well as cognitive elements, which provide the infrastructure of the organization. To handle these institutional aspects, school principals use adaptive strategies, such as bridging and buffering.