The dynamically changing sociocultural and educational environment is a source of personality development in each age group. It has enormous potential for educating human dignity associated with the freedom of choice and the responsibility for it, and at the same time creates rapidly increasing psychological and pedagogical risks. The aim of the article is to consider the ethical and pedagogical aspects of formation of an assertive personality in the context of psycho -pedagogical facilitation including diagnostics of assertiveness in different age groups. Assertiveness is considered a systemic property of a personality, consisting in the ability and willingness to form independent opinions freely and openly, to show faith and trust in others, and to be able to regulate their own behavior and personal identity. To achieve these goals, psychological and pedagogical support and facilitation of a person at any age are necessary (C. Rogers). Are professional educators ready for it? Are they aware of the theoretical and methodological foundations of this concept? Do they have the appropriate innovative technologies, including the criteria for evaluating the achievements of students at different levels of education? How can we practically help teachers master the corresponding general cultural, general professional and specific professional competences in the context of the theoretical and practical novelty of the new educational paradigm, a personality - oriented model of learning "through life"? Traditional ethical, pedagogical and psychological mechanisms of socialization dominate children and make the personality unprotected from peers, parents, teachers and other adults. Individual needs, desires and interests get lost; the growing person lives by external evaluations, forcing submission and suppression of the Self. If these issues are not dealt with in terms of assertive behavior, it leads to personality deformation, cuts down interpersonal relations and increases risks of conflict behavior.