In an ever-changing world, the goals of education and the expectations of education policy makers, society and parents for the education system are also changing. Pre-school educational institutions need teachers with professional excellence and leadership skills who are constantly improving their competencies. In this context, the management of a teacher’s career is becoming a particularly important issue. In the management of a teacher’s career, not only the motivation of the teacher himself but also the role of the headmaster is very important in creating conditions and providing opportunities for the development of a teacher’s career. The article reveals the attitude of headmasters in pre-school educational institutions to the possibilities of pedagogue career management. It presents the results of qualitative research (interviews with headmasters in pre-school institutions), which revealed that headmasters understand the importance of teachers’ career management both for the teacher himself and for the quality of the institution’s activities. Some headmasters take care of a teacher’s career, creating conditions for improving competencies, and providing financial and psychological support. However, not all headmasters in pre-school institutions create favourable conditions for the development of a teacher’s career by delegating this function to the teacher himself.