The relevance of the study is determined by two factors. On the one hand, the study is relevant due to the priorities of modern educational policy, which provides for the development of mentoring at all stages of the educational process and, above all, in the fi eld of personal development. On the other hand, the lack of theoretical and methodological background to the issue of mentoring in psychology and pedagogy makes it topical. The purpose of the study is to develop a typology of mentors’ pedagogical positions and to analyze the influence of different types of positions on the personal development of students. The study hypothesizes that by taking a certain pedagogical position a mentor forms an appropriate environment type, which, in turn, forms a certain personality type. Methods (tools): typology of objects based on the vector modeling of the personality-developing environment. Results: the study presents an original typology of pedagogical positions of mentors, including teachers and parents, which determine the educational microenvironments that shape the personality. The following pedagogical positions of mentors have been identified: "coach", "boss", "commander", "conductor", "shepherd", "waiter", "expert", and "consultant". Parents can take on specific roles of the "ambitious jockey", the "executive bureaucrat", the "unyielding guru", the "fashionable decorator", the "detached workaholic", the "generous Santa", and the "reflective gardener". Main conclusions: by adopting a specifi c role, mentors create an environment type that is characterized by a specific level of freedom and a level of personal stimulation. This typology is complementary to Janusz Korczak’s typology of “educational environments,” which includes the dogmatic environment, the serene consumption environment, the ideological environment, and the superficiality and career environment. According to P. F. Lesgaft’s “school types,” which include ambitious, hypocritical, harshly-oppressed, mildly-oppressed, oppressed, good-natured, and normal types of students, the study shows the correlation between the environment type and the personality type developed in a particular environment. The study presents a causal chain that consists of the following elements: the mentor’s pedagogical position – specific educational environment – the resulting personality type. The practical significance of the study lies in the ability of mentors to understand and adjust their pedagogical positions to manage the personal development of their students.