Pedagogical competencies – motivation, communication, interpersonal relations, innovating and change-making are extremely important in almost every field of work worldwide, and with monitoring of teaching included among them, they are altogether especially significant in education. Since headmasters are people at the head of every school unit, it is crucial that they possess various competencies, among which pedagogical ones should most definitely be included. Accordingly, this paper discusses the headmaster's role as managing and expert leader of the school with an emphasis on his fundamental functions. There, an image of what headmaster exactly does in school and how he impacts the progression of his school through these functions is given. The role of basic competencies is stressed and after them, the emphasis is put on the role of pedagogical ones that are necessary for successful school leading. After that, the results of empirical research are shown. The main purpose of this research was to explore examinees’ views, opinions and experiences about specific areas of pedagogical competencies and to prove that their use leads to more successful educational practice. To provide this insight, the used method was interviewing, which contained 5 fundamental research questions that matched pedagogical competencies already listed. Examinees were headmasters of several elementary schools. To conclude, research results show that headmasters included in this research think that they possess pedagogical competencies and are aware of their importance in optimal performing of headmaster’s job. However, it has been shown that each examinee understands and uses those competencies in their own, different way. That is not necessarily a bad thing, but it certainly implies the need for constant emphasizing of pedagogical competencies’ importance, as well as their development in formal and informal education of all pedagogical employees who might one day become headmasters themselves.