As difficult situations around educational management increase, related research needs to be reflected upon. In this research, the actual nature of the school management process is examined by questioning "How is a headteacher able to impact and effect the school?" and "What kind of relationships are there among various people who are involved?" using the fieldwork at the R school alliance (consisting of four primary schools and one lower secondary school) since 2013 in Japan. As a result, it is shown that the following phases are needed to be considered--various intentions and people within/outside the school; rotation system as the personnel affairs; careful mutual-understanding with educational administration to overcome the "top-down" approach; and sharp insights into social changes. It implies that even under a uniform system the reality of school management is very diverse, and the possible ways for the corresponding school management are particularly context-dependent. So even the simple technical theories can become harmful. Therefore, dialogue between school leaders and researchers is essential to find alternatives and/or follow global trends while understanding the complexity of school management in relation with the meso/macro contexts such as community conditions and educational policies.