The purpose of this study is as follows. First, I would like to examine the patterns and causes of changes in the Office of Education that occurred after the implementation of the system in which residents directly vote and elect the superintendent of education. Second, I analyze the positive and negative types of the educational supervisors and examine the structural constraints they face. Third, I would like to suggest the roles and tasks of educational supervisors required in the era of self-government education. For these purposes, interviews were conducted with 15 people, including teachers and tenure-term officials, who worked, or interacted with educational supervisors. The results of analysis are as follows. Since the emergence of superintendent through direct voting, positive changes have been confirmed in the Office of Education. The cause of the change was analyzed as ① election mechanism ② superintendent's leadership ③ transition committee and governance ④ human resource replacement and inflow of various resources ⑤ inflow and activity of professional staff with field practice experience. There are three structural constraints experienced by education professionals: the Ministry of Education, the Office of Education, and educational supervisors The types of educational supervisors are divided into positive types and negative types. The positive type was named ① innovator type, ② learning community participation type, and ③ field network utilization type. Negative types can be classified into ① authoritarian type, ② incompetent type, ③ status quo type, ④ promotion-oriented type, and ⑤ self-experience confidence type. Based on these analysis results, I proposed the roles and tasks of educational supervisors.