The aim of the research is to confirm whether gender, age, residence in rural or urban areas and work experience influence the peculiarities of hierarchy of leaders’ personal values, and also to investigate the differences in the hierarchy of leaders’ personal values and that of their subordinates. The significant changes in the social value system create for the majority of people the urgent need to adopt new benchmarks and rebuild their personal values system. This also applies directly to the modern leader who is trying to reach a mutual understanding in the relationship. The goal of our research is to study the peculiarities of the hierarchy of leaders’ personal values. These were the hypotheses of the study: 1) the specific and individual-oriented values prevail in leaders as well as values of “business” and “self-affirmation”; 2) the hierarchy of value self-determination of modern leaders in education is influenced by their work experience, residence in rural or urban areas, age and gender. To solve the empirical problems of our research and to confirm or refute the hypotheses, we used the method of studying the value orientations, developed by the American researcher Milton Rokeach. According to the results of the research, the most important leaders’ terminal values have been the specific and individually oriented values, and the most important leaders’ instrumental values have been mainly the values of «business» and «self-affirmation», while gender affects the terminal and instrumental values, and the age impacts mainly instrumental values.