Improvisation can be an important element of mediation practice, and there are several ways in which mediation practice correlates to improvisational performance. In this article, two mediation experts and two skilled jazz musicians explore the improvisational aspects of mediation. Two central themes emerge: (1) mediators often use improvisational techniques, and (2) by being improvisational, mediators can create environments that would encourage the parties themselves to be improvisational. We argue that practitioners can enhance their effectiveness as mediators by mastering improvisational skills.