In these days of overwhelming clinical work, decreased resources, and increased educational demands, time has become a priceless commodity. Competency-based medical education attempts to address this challenge by increasing educational efficiency and decreasing the “steeping” of learners in clinical activities for set durations of time. However, in this environment, how does one teach for compassionate, humanistic practice? The answer arguably lies in clinician–teachers’ recognition and engagement in a different type of time, that of kairos. Ancient Greek thought held that there were 2 interrelated types of time: chronological, linear, quantitative time—chronos—and qualitative, opportune time—kairos. Unlike chronos, kairos involves a sense of the “right time,” the “critical moment,” the proportionate amount. Developing a sense of kairos involves learning to apply general principles to unique situations lacking certainty and acting proportionally to need and context. Educationally, it implies intervening at the critical moment—the moment in which a thoughtful question, comment, or personal expression of perplexity, awe, or wonder can trigger reflection, dialogue, and an opening up of perspectives on the human dimensions of illness and medical care. A sensibility to kairos involves an awareness of what makes a moment “teachable,” an understanding of chance, opportunity, and potential for transformation. Above all, inviting kairos means grasping an opportunity to immerse oneself and one’s learners—even momentarily—into an exploration of patients and their stories, perspectives, challenges, and lives.