The “Chatbot for diagnostics of communicative skills of counteraction to psychological pressure” was developed and tested on a sample of students. The bot imitates the situation of communication in real time and helps to assess the level of development of communicative skills identified in the analysis of the literature as skills of counteracting psychological pressure: the ability to recognize situations of psychological pressure; the ability to verbally express their emotions and desires in a socially acceptable way (“I-speech”, the ability to say “no”); the ability to use different ways of “listening”, depending on the content of the information transmitted by the interlocutor (active, empathic, passive). The method proposed by the authors showed high values of reliabilitystability (retest) and reliability-consistency. The validity of the methodology was confirmed by high discriminability values, as well as by additional methods of validity assessment (formative experiment and sentiment analysis using the TextBlob text library).