In this introductory chapter we first reflect on the meaning and nature of modern democracy by focusing specifically on its historical amalgamation with liberalism. We then examine the notion of practical reason or judgment on the assumption that good leadership must depend crucially on a capacity for good judgment. We contrast classical conceptions of judgment with modern ones to argue that modern theorists effectively 'democratized' judgment in a way that caused its reduction to two mutually incompatible conceptions: amoral, self-interested calculation on the one side; and the application of strict moral imperatives on the other. We claim that, if good leadership is to be properly understood, we need to return to a more unified account of judgment in which interests and ethics are not necessarily opposed. We then outline five major themes this book seeks to explore, namely: the definition or meaning of good democratic leadership; the question of the education of leaders and of citizens; the conditions required to make democratic leadership effective; the importance of institutions and their influence on leadership performance; and, finally, some enduring challenges to securing good leadership in democracies.