The educational and social environment has an obvious influence on principals' subjectivity of school management. If principals could try to break through the possible restrictions and oppression, and then they would become leaders with subjectivity. This article explores the principals' subjectivity of school management through the literature review and researcher's practice and observation at school. Firstly, it explores the meaning and influencing factors of principals' subjectivity of school management. Secondly, it analyzes the generation process of principals' subjectivity.