Article is devoted to experience of studying regularities of development the personality in the conditions of collective interaction in creative organizing activity. Fully such conditions are created by an educational system based on the pedagogical concept of I.P. Ivanov. Objective of this research: to reveal specifics of socio-perceptive images of the person (including self-images and images of the senior companion) and life-meaningful orientations of the different generations included in collective creative organizing activity. Research methods: V.L. Sitnikov’s technique “Structure of an image of the person (hierarchical)” – SOCH(I), the test of life-meaningful orientations of D.A. Leontyev, the questionnaire. Research showed that active participation in the advanced school age in collective creative activity has essential impact on formation of life-meaningful orientations, images of yourself and other people.