The research aims to explore empirically the competences-based teaching and assessment practices of 19 Italian secondary school teachers through a focus group methodology. The meeting was the starting point for a professional training course on inclusive learning design using multimodal digital environments, i.e. social network sites and the Web 2.0. Results show that the competences-based framework adopted at an institutional level more than one decade ago did not impact the knowledge-based teaching and “intuitive” assessment practices of participants. These conclusions advance the understanding of the weak relationship between educational policies and teaching practices in the Italian context. Furthermore, interesting limits toward pedagogical and digital innovation in secondary school emerged. In particular, the learning practices of young people in social network sites and Web 2.0 were identified as the most influencing factor on the perceived detachment between participants and their students. As a consequence, teachers stigmatised these technologies, revealing marked tensions while introducing ITC and innovative digital pedagogies based on new forms of learning.