In this paper we argue that creating and implementing a monitoring system for psychosocial development of schoolchildren is reasonable as it is one of the most effective and easily applied means of addressing a number of significant tasks, both psychological/pedagogical and organizational/administrative. In the context of testing the general hypothesis that the introduction of the monitoring system will promote individually oriented approach to learning without radical transformation of the existing secondary education system we developed and verified a set of techniques to be used in the monitoring, including the following: differential of psychosocial development, technique for defining group value orientations, and a social psychological modification of G. Kelly’s repertory grid. The paper presents outcomes of a study that aimed to prove the heuristic character of the chosen theoretical and methodological approach; it was carried out on a sample of children of 6th—10th classes of the Moscow school #1409.It is shown that monitoring of psychosocial development of schoolchildren helps to reveal educational and developmental difficulties and develop effective means of psychological and pedagogical intervention taking into account the specifics of a particular educational institution.