Introduction. The organization of the educational process in modern social conditions is focused on the realization of personal potential, as well as on informing students. The mechanisms of personality-oriented education do not always contribute to the subjectivity of interaction between participants in the educational process, so the personal potential is not fully revealed and realized, which reduces the effectiveness of the educational process. The construction of a personality-oriented education is relevant. The purpose of the article – determining the potential of pedagogical assistance in the system of personality-oriented education and in the construction of situational and environmental interaction of educational process subjects. Methodology, research methods. The research is based on the holistic principle of the integrity of phenomena; the principle of the system that ensures the interrelation of components of the pedagogical process; the activity principle in ensuring pedagogical interaction; the personal principle in facilitating pedagogy; the subject principle as the basis of self-consciousness; the heuristic principle of creative self-realization of subjects of educational interaction; the situational-environmental principle as the basis for building active education. Research results, discussion. The article scientifically substantiates the content of pedagogical assistance at the stages of the cycle of situational and environmental design of personal development trajectories of interaction subjects in education. The article describes the features of situational and environmental design of personal development in education, the role and organizational aspects of pedagogical assistance to students in situations of self-knowledge and self-determination, self-actualization and self-esteem, self-awareness and self-regulation, self-affirmation and self-realization. Conclusion. Generalizing conclusions concerning the realization of the potential of pedagogical assistance as an element of the organization of personality-oriented interaction of educational subjects are presented. Creating an educational environment based on pedagogical assistance in educational interaction contributes to the development of students ‘ personality, their abilities to transformative activities in the environment of life.