In Europe, the reference for the digital competence profile of teachers is the framework of the DigCompEdu (Digital Competence Framework for Educators). The goal is to support teachers in monitoring their digital pedagogical competence, organized into eight competence profiles and six development areas, two of which concern the use of digital technologies. The Erickson Publisher has developed a skills Syllabus for the “Expert Teacher” divided into three macro-areas, linked to a training course. During the 2020 lockdown, a survey research was administered to more than a thousand teachers engaged in Distance Learning. The comparison between the data collected and the two models evokes reflections and suggestions to promote the development for the digital skills of the 21st century Teacher.