This research project analyzes a strategy for teaching philosophy in secondary school inspired by Socratic dialogue, which aims at the creation and effective management of cognitive dissonance as a tool for promoting critical thinking, called Socratic Challenge (SC). The research originates from workshops held in the years 2016/2019 in a technical and vocational institute in the province of Varese, in which I participated as the creator and conductor, involving the voluntary participation of about 150 students. The research questions are: What (...) are the characteristics of the Socratic Challenge? Can it constitute a teaching methodology to be proposed? Under what conditions? Within what project framework? The empirical research is qualitative, naturalistic, and exploratory (Lumbelli, 1984), specifically a self-study (Hamilton & Pinnegar 2009), divided into two phases. In the first phase, data regarding motivation and perceptions of training impact were collected through in-depth interviews of students (16) and analyzed using the criteria of reflective thematic analysis (Braun & Clarke 2019). In the second phase, the workshops were repeated remotely in technical and vocational institutes in Milan and the province, involving 113 students who were surveyed with a qualitative questionnaire. The workshops were recorded and the discussion interactions were analyzed according to a qualitative inductive approach that refers to Constructivist Grounded Theory (Charmaz, 2006). Results show how this dialogical instructional strategy in philosophy teaching can be considered an effective alternative to the historical-philosophical approach predominant in the Italian tradition (Illetterati 2007). (shrink)