This article focuses on the relationship between administrative discretion and the rule of law, showing that administrative discretion properly conceived is not only compatible with a particular understanding of the principle of the rule of law but could also become a vehicle allowing the executive to express its commitment to that principle. In the author's view, this is possible if, first, discretion is conceived through the metaphor of a dialogue between rulers and ruled; and, second, we endorse a substantive understanding of the rule of law that views all three constituents of the state – legislative, judicial, and executive branches – as involved in the project of preventing arbitrary action by public powers. The article explores these dynamics in the concrete setting of the author's experience as associate dean of a law school, in order both to see how the theoretical model of dialogue translates into practice and to identify the particular aspects of the theory that might require further inquiry and empirical research.