This paper focuses on the experience of traineeship for “second level” Adult Educators in the Master Degree Course in Pedagogical Sciences of the University of Milano Bicocca. First, it draws the normative and institutional framework related to the profile of the second level professions in the educational field, such as coordinators, supervisors, consultants, as well as trainers of educators, of teachers, and of other care professionals. Second, this paper analyses the traineeship educational project, highlighting its theoretical and methodological assumptions and its functioning as a “pilot” experience of tutoring. In the end, the article shows the new project of traineeship for second level adult educators, a project that derived from a critical process of evaluation of the pilot course.