The authors of this paper, while observing the Polish education system, can not accept the ossified administrative structures existing in the system and the triumph of economic objectives over the human ones, the latter understood as individuals having the opportunity for self-realisation (developing one's subjectivity). We want to ask what identities an education system functioning in this way would create? A lot of attention is devoted in the literature to the problem of education. We also want to speak on this matter, for the sake of the common good which education undoubtedly is. We sincerely hope that the perception of problems in the system will lead to its repair and not its destruction. This paper consists of two main parts. The first part presents the reconstruction of critical theory based on the philosophy of Theodor Adorno, Max Horkheimer and Jurgen Habermas, which concerns the concept of subjectivity. The notion of subjectivity emerging from the thoughts of the representatives of the Frankfurt School is then confronted with the image of man created by the Machiavellian thought, according to social sciences. This is followed by a description of the Machiavellian personality trait, based on the psychological interpretation of Machiavellianism, and not on the current philosophical interpretation. In the second part, the authors present the proposal for using computer exploration methods to identify Machiavellian behaviours. The proposed solution takes into account cognitive, educational and preventive aspects
