In recent years, a deep digital transformation has been taking place within education at all levels; the Covid-19 pandemic has given a strong acceleration to the use of new technologies for teaching and created a new approach to life. The digital evolution of experiential contexts is embedded both within the social interaction between individuals and within organizational, educational contexts. This contribution intends to illustrate an orientation experience with undergraduates’ students carried out within the framework of initiatives aimed at fostering employability. The training path has been realized by the Career Services of Roma Tre University and Lazio Region within the “Porta Futuro Lazio” project. The activities took place online through the adoption of self-guidance and self-assessment tools (questionnaires), interviews and focus-groups aim to increase self-guidance skills development process and employability.