Schools have been responding to the ongoing digital transformation, which requires continuous self-reflection and decision-making skills from teachers in the inclusion of new digital technologies in the teaching and learning process. In the present study, descriptive measures were used to understand how 140 teachers, in a school group, perceived their digital competences through the Check-in Questionnaire (Study 1). A school group is a Portuguese organisational unit, constituted by different schools, catering to different age groups, managed by a single director. Study 2 addressed how this specific school group organised teacher training courses, considering the results of Check-in Questionnaire, and the scope of the National Digital Transition Plan. Interviews, in which data content analysis was applied, were undertaken with seven teacher instructors, selected to implement digital training. The results of Study 1 revealed that most teachers are positioned at level 2, an intermediate level, with no differences in age or years of service. In Study 2, instructors revealed that the proficiency level assigned in the Check-in Questionnaire did not always correspond to a teacher's real digital skills, identifying this as one of the obstacles to achieving the initial training aims. The goal of the training was for these professionals to feel committed to their educational context and understand what is intended in the inclusion of digital skills in the classroom. The relevance of this study relates to the current context, which places education and teachers at the centre of a digital agenda focused on the development of digital skills, thus generating new pedagogical practices, while accompanying the process from the initial assessment to the implementation of training in the National Digital Transition Plan.