Abstract: This article introduces the main results of the self-assessment data collected for the Comprehensive Schools in the Digital Age -project (2016–2018) from the viewpoint of the schools’ strategy work and teachers’ and principals’ digital competence. The target groups were the principals and teachers of schools providing basic education. Over the two-year follow-up period, there has been some positive, yet slow progress in the strategic work in schools. Increasingly often, the schools have a common vision on digitalization, and its realization is supported in the working communities. Teachers’ and principals’ digital competences have gradually increased and their overall self-assessment results show that these key players on changing the school culture are in the basic and advanced level in utilizing ICT in their work.