A municipality in Sweden took initiative to enhance the competence for all principals to lead digitalization in schools. The initiative was implemented during 2018-2019. Participant observations and surveys were used to document results, which showed a gap in the chain of command, as well as different attitudes towards the course between school and preschool principals. The attitudes were more mixed among the school principals than preschool principals, who were mainly positive about the initiative. The study suggests that leading digitalization through a chain of command should be done as a process, not a project, enabling integration of multilevel organizational aspects over time.