The reason why school teachers need leadership is that there is a wide variety of concepts of “demands” in schools including socially diverse requirements over schools and complicated admission systems. However, when a school faces burdens of challenges like collecting various opinions of parents and students in today’s increasing demand including accomplishments of various school goals with successful exertion of teachers’ expertise, a head teacher’s leadership as an intermediate leader is essential to overcome the limitations to manage the school. In this study, Strauss & Corbin s Grounded Theory method was used. The reason why Strauss & Corbin s Grounded Theory method was used is that this research mainly focused on social interactions. The conclusion of this study is as follows. First, the grade head teacher of a senior high school is showing leadership of ‘Dokbak’, which means a solitary confinement. Second, Dokbak’, a solitary confinement leadership, of a grade head teacher results not from an individual problem, but from the scene of schools. The very end of the educational administration organization is the class organization that directly teaches, directs, and coaches the students who will lead the future society, and the school year organization. No amount of effort and emphasis on reforming education at the national level will achieve the originally intended educational reform if it loses its original meaning in the lowest-level of class and grade organizations. Through this study, I hope that the senior high school grade-head teachers will show their leadership, that the senior organization will be revived through research and practice on senior high school teachers leadership, and that the school organization will perform its functions more properly, thereby developing education in Korea.