The deployment of ICT in school setting is in many ways a complex managerial task that involves several stakeholder groups. Firstly, principals and deans have to relate to the local, regional, national, and international policies and governing systems. Furthermore, the voices of teachers, students and their parents have to be considered and negotiated. In this paper, we explore how school principals’ and municipal IT-managers’ perceive the usefulness and the potential role that ICT play in the school context. In a pilot study of a single school district in a Swedish municipality, we have interviewed representatives from the municipal board of education, the municipal IT-support for schools, and two principals. By using the Technology Acceptance Model (TAM3) as an analytical lens to understand the two constructs of “Perceived usefulness” and the possible role of ICT, we conclude that the barriers for successful integration of IT into educational practices requires firstly overcoming the lack of coordinated ICT investment strategy and tracking of ICT. This can be done by having a clearly articulated ICT policy distributed to school staff which we argue will positively influence the perceived usefulness as expressed by principals and their governing body. Secondly, inclusion of ICT in all aspects of teachers’ professional school activities will bring change to school activities and processes.