The Industry 4.0 paradigm and all its connected technologies (Big Data, Internet of Thing, Artificial Intelligence, Cloud Computing, Machine Learning, Augmented Reality, etc.) are quickly and deeply impacting on the companies’ organization and technical capability. Although it is commonly accepted that the “digital shift” is an essential requirement for the companies’ competitiveness, the Industry 4.0 paradigm has also introduced several relevant changes in the competences and skills of employees and managers, that may be a bottleneck in the adoption of the Industry 4.0 model. Some initiatives have been created at European level to support the education in the context of Industry 4.0. In this paper we present a selection of them, focusing in particular on the innovative didactic methodologies adopted in each different initiative.