This paper examines how principals in Greek schools’ foster teachers’ professional development through strategic incentives and motivational support, highlighting the critical influence of leadership on educators’ growth and engagement in professional training programs. The main purpose is to explore the role of principals in encouraging teachers’ professional development. The aim is to obtain a valid and reliable case and to draw a clear conclusion on how principals influence teachers in the Greek vocational schools’ environment. The literature review has taken place in Greece since there has been a significant shift to professional development, and more educators tend to participate in innovative programs. According to the results of the research, principals are the main type of leader who influence teachers towards their professional development. The main motivation of managers is based on the use of incentives related to the promotion for social participation and work satisfaction, but also of those incentives that are related to finances, especially when these lead to professional development. A key element in engaging teachers in programs that will enhance their professional development is the motivation they receive from the school’s management or principal. Nevertheless, the more time and effort that will be acquired for their training, the more effective and intensive the influence they receive must be.