Abstract The world of work is replete with daily hassles that make the experience of negative emotions ubiquitous. Conversations between leaders and followers during challenging times are often characterized by negative emotions, and thus, are of central importance in modern organizations. Yet, the intersection of negative emotion, difficult conversations and leader–follower relationships is often ignored, and these topics are treated as separate areas of study. We integrate these various streams with research on asymmetrical leader negative emotion displays to identify when and how difficult conversations laden with negative emotions result in benefits to leader–follower relationships. Using a grounded theory approach, we build a theoretical model based on interviews with 21 leaders and 17 followers describing 166 difficult conversations. Our work depicts specific communication strategies that leaders use to facilitate difficult conversations. These strategies, in turn, create shared meaning and validate followers' feelings during difficult conversations, which allows for beneficial relationship‐specific outcomes to ensue. We unpack these findings in the context of the power differential between leaders and followers to advance current thinking on the intersection of negative emotions and communication in leader–follower relationships.