Collaborative problem solving (CPS) is a process that relies on both cognitive and social skills contributions by those involved in the joint activity. If a student is matched with a problematic group of peers, then there will be no valid measurement of the CPS skills. In the human-agent settings, CPS skills are measured by pairing each individual student with a computer agent or agents that can be programmed to act as team members with varying characteristics relevant to different CPS skills and contexts. This paper describes current research on measuring CPS skills through human-agent interactions in a prototype of a collaborative educational game.