Expert negotiators and mediators need to create, recognize, and seize the moments that are critical for a successful negotiation or mediation. Doing so requires “practical wisdom”—a term that dates back to Aristotle—that cannot be “taught” in any simple or straightforward way. Such wisdom can only be learned through practice. This article considers how the practice of negotiation, and professional practice more generally, can be structured to encourage the learning of practical wisdom. In particular, how do professional negotiators and teachers of negotiation encourage their students and colleagues to learn the character traits and skills necessary to recognize and act well in “critical moments?”