A growing body of initiatives aims to connect school improvement with external actors, such as universities, by means of networks and collaborative partnerships of different kinds. Simultaneously, many schools have difficulties in assessing or predicting their needs associated with the digitalization of a specific local school practice given their lack of existing tools to articulate those needs. This has made it difficult to study digitalization in a complementary and symmetrical way between academia and practice. In this study, we used a quantitative instrument to generate findings and development needs relevant to both research and school development. The instrument, which we distributed to all school leaders in one municipality, measures perceptions of three overall areas: (a) levels of digitalization, (b) organizational digital maturity, and (c) notions of leadership. The data shows, for example, that digitalization, in this municipality, was a concern or issue on an individual level. Achieving a more complex view of digitalization as school development—a collegial approach and mindset together with leadership and organization that focuses on strategy and common goals—appears to be a high priority for research and practice. To conclude, the results generated from the instrument used in this study can contribute to a shared understanding of the findings and the needs relevant to both research and school development.