The article considers the problem and the importance of formation of the active personal position of schoolchildren. Active personal position is a complex concept, which includes the ability to a problem solution, the ability to work in a team, the ability to express his or her views. The formation of an active personal position at school is necessary for the further development of the personality and the ability to evaluate their own activities in the society. Assessment and monitoring system is needed for complex and comprehensive development of active personal position. Thus, the purpose of the article is to develop such system theoretically. For this purpose, the methods of analysis, synthesis, and theoretical modeling were applied, and psycho-pedagogical and methodological literature was studied and summarized. The developed theoretical assessment system of active personal position of schoolchildren allows to devise an individual approach to each child based on the evaluation results, as well as to develop new methodological approaches for students' development.