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In the latest educational policies at national and European level, lifelong guidance is increasingly identified as a key instrument to innovate and strengthen the provision of schooling to reduce school dropout and develop students’ adaptive capacities in a context of growing job flexibility. Guidance activities constitute indeed a key setting for the development of Career Management Skills (CMS), those abilities needed to support students in their transitions through education, work and training. By looking at the Italian context, our paper outlines how lifelong guidance policies, and the technological mediation used to make them operational, constitute crucial devices promoting changings in teachers’ professional culture. In particular, we analyse how teachers are recruited into a new pedagogical paradigm and we reflect on if and how this opens or closes spaces for developing processes of empowering or domination, especially for students from an underprivileged background. In the paper, we discuss the case of the recent introduction of a career guidance software in Italian schools, named SORPRENDO, whose aim is to improve the quality of guidance services in Italy and provide an e-learning platform where teachers can support and evaluate the future planning of students. First, we provide a theoretical reflection on the agential effect of digital devices in the governing of education, in particular through their interaction with teachers’ practices; secondly, through an empiric case study research, we show the types of educational practices the software makes ‘affordable’ within the Italian school context, and the organisational and cultural tensions it creates. We conclude by reflecting on the impact of the lifelong guidance project on the pedagogical relationship between teachers and their students, highlighting limits and opportunities.