The content of notion “personality`s individuality”, individuality as a basis for successful professional activity, the optimal forms of organization and management of a training process aimed at self-education and development of individuality are in the focus of the authors. The psychological and pedagogical conditions of origin, formation and improvement of individuality in high school training, its relationship with person`s creativity are considered by the authors. According to them, the development of individualities of future specialists should be the main goal of any educational institution, and in this connection the authors propose the correction of requirements to educational system, its structure and content, paying attention primarily to personality-oriented organization of training process. The problem of development of personality`s individuality is examined on the example of the military high school for which it is especially actual problem. The role of teachers, commanders, senior officers and instructors in the formation and development of students` individualities is revealed.