On the basis of an empirical inquiry carried out at one major short-cycle tertiary education institution in Lombardy, the authors reflect on the educational role of tutors who accompany higher technical education students during their course and in particular through their apprenticeship and traineeship’s experience. These figures undoubtedly help the learning process, which in the cases taken into consideration occurs in alternation between classroom lessons and on-the-job experience, but their function seems to be closer to coaching. They also perform mediation and facilitation tasks, which are very important both for students and the entire learning organization. More precisely, they support their tutees in the orientation process, as well in the acquisition of the professional habits. The pedagogical challenge of investing in tutoring figures is still open, not only to guarantee the educational accompaniment needed by young people entering the world of work for the first time, but also to foster the learning process directly and intentionally. The full educational and cultural – and not only occupational – enhancement of higher technical education also depends on this.