School leaders who have advocated for controversial programs know the pitfalls. Among the most frustrating are individuals and groups who resist any change at all, those who are supportive but remain silent, and those (opponents and allies alike) who are so passionate in their position they seem unable to hear the views of others. Each group presents challenges for administrators and can put a proposed or existing program at risk. Each individual is guided by moral views about how the world is and how it should be. Increasingly, such individuals organize into advocacy groups that push a particular moral stand on an issue and are ready to storm into action when and if that issue arises. Understanding these differences in moral perspective and how they can be addressed directly in program advocacy can increase the effectiveness of those who lead. School leaders face a moral dilemma of their own: how to advocate for necessary programs, while respecting the diverse views of stakeholders. Understanding how individuals view issues through their own moral lenses and knowing how to articulate advocacy messages accordingly so that they can be most widely heard can help administrators more successfully gain and retain support for controversial programs. This article discusses the cultural divide that affects education in many ways.