Techniques for assessing the proficiency of artificial intelligence agents and users in a given knowledge domain are described. A plurality of proficiency agents can be initialized with a plurality of proficiency scores, by performing a plurality of assessments between pairs of proficiency agents selected from the plurality of proficiency agents. A first client device associated with a first user is matched with a first proficiency agent of the plurality of proficiency agents, based on a first proficiency score associated with the first user and a second proficiency score of the plurality of proficiency scores corresponding to the first proficiency agent. Assessments results of an assessment performed between the first client device and the first proficiency agent are received, and a rating system update function is used to update the first proficiency score and the second proficiency score, based on the assessment results.