The importance of trust in institutions in Japan is a common theme that emerges from literature on Japanese institutions. This article presents a problem-based methodology investigation into a Japanese educational institution, and how a Japanese educational leader deals with student incidents. A theory of action detailing strategies chosen in that institution for communicating student incidents to parents, a set of constraints that explains how those strategies came to be chosen, and the likely consequences of those strategies is described. Our analysis reveals that the goal of maintaining relationships and avoiding conflict with parents in order to maintain trust in the institution drive decisions about how to communicate with parents about student incidents. However, we conclude that the chosen strategies are unlikely to achieve the desired ends. We conclude by proposing an alternative theory of action that is more likely to achieve the stated aims of the school leader.