The purpose of this study is to explore the role of leadership communication incultivating compassion at work. To do so, this study utilizes positive deviance case selection and qualitative, semi-structured interviews to explore employees’ experiences with highly compassionate leaders. These interviews allow insight into employees’ perspectives on expressing suffering at work and experiences of compassionate communication from leaders. The findings of this study extend current understandings of compassion at work by highlighting the role of uncertainty to express suffering in limiting compassion, uncovering leadership communication behaviors that cultivate compassion, and illustrating dynamics that leaders navigate when reacting compassionately. Specifically, this study extends compassion theory by (1) demonstrating that uncertainty related to emotional disclosure limits employees’ sharing of personal suffering, which shapes and limits compassion processes, (2) illustrating that individuals holding traditionally marginalized or minoritized identities face additional uncertainty related to expressing pain and suffering, (3) highlighting a relational orientation that emphasizes personal well-being as enabling the compassion processes, (4) outlining anticipatory compassion as a specific discursive move that conveys care and opens space to express specific pains and suffering, and (5) empirically illustrating three dialectical tensions that punctuate the dynamic interactions between leaders and employees when relating and (re)acting compassionately.