Distinguishing between problems that have solutions and dilemmas that need to be managed, the authors identify three overarching questions from the School ABC case that center around data and perceptions. Because the ability to talk openly and honestly about difficult issues is critical to the health of a school, the authors consider the obstacles and opportunities school leaders face when trying to tackle the complex issues raised in this case. Central to these issues is the degree to which managing conflict dominates leaders' work, and the authors offer suggestions for the leader of the case school that are transferable to other settings. These include understanding the underlying perceptions and emotions of students, faculty, and parents. School leaders who see their primary task when facing complex school culture issues as understanding the feelings and perspectives of all the stakeholders will have the best chance of addressing the issues and improving the learning environment.