This article argues for the centrality of imagination in effective school and classroom leadership, by focusing on two notions, vision and empathy. In addition, some implications for the role of education in fostering students’ imagination are also discussed, such as “seeing in students their hidden potential” and “reading the story of the other.” Such implications are based on the empowering role of imagination, which is crucial for furthering the dialogue and thus for advancing human progress. The central argument is that effective leadership is about leading people with imagination. And such a conception of leadership points to a differentiation between what this article calls “imaginative leadership” and other types of leadership, on the grounds that their central and defining characteristic is not imagination.