What can Adam Smith can teach us about the emotional terrain of difficult conversations, particularly those that touch on lived realities of injustice, oppression, and marginalization? In Part One of the Theory of Moral Sentiments, Adam Smith takes a few pages to dwell on the topic of interpersonal disagreement: more specifically, on how differently we feel about disagreements “with regard to such indifferent objects as concern neither me nor my companion” (TMS, 21) than we do when our own fortunes, feelings and even identity are bound up in the topic at hand. I argue that careful attention to Smith’s discussion of disagreement reveals a set of norms for navigating uncomfortable terrain that avoid the pitfalls of so-called tone-policing and other contemporary approaches to civility.