School is a place used to gain knowledge. A good school will also be able to produce good graduates. To make it real, the school must have staffs that are professional in their respective fields such as principal, teachers as well as employees to create such school. Principal is the leader key who will be the director in developing a good school so that it can produce graduates who are ready to work in the community, particularly in the Business World and Industrial World (BWIW)/Dunia Usaha dan Dunia Industri (DUDI). The role of principal in school development is very important, both in controlling and guiding teachers to become professionals in their field and also all employees who help in developing the school so as to provide good services for learners. Particularly, vocational school teacher is an educator who has a great responsibility not only to transfer theoretical knowledge but also to develop the skills of learners' psychomotoric aspect. Based on the things above, the control and the role of principal are necessary to help develop teacher's way of thinking, to improve teachers' productivity and to improve their skills that will be transferred to the students. Many things a principal can do to develop ways of thinking of the educators in order to develop work productivity, such as providing training that helps teachers develop ways of thinking and expertise in psychomotoric competence to improve the learning process in the classroom. This study aims to determine how the role of principals in the empowerment of teachers' post-skill training in developing critical thinking skill to improve work productivity.