Many scholars have attempted to make jazz relevant to an organizational audience. We seek to extend this literature by considering a more radical version of improvisation associated with the jazz musician Ornette Coleman. Inspired by an encounter between Coleman and the philosopher Jacques Derrida, we juxtapose the radical collective responsibility associated with Coleman’s Free jazz improvisation and Derridean deconstruction. We especially emphasize a phrase used by Derrida, "a certain experience of the impossible," as an expression for a particular experience of doing management. The overall contribution of the article is to explore the possibility of responding to issues within organizations in more participative and improvisational ways, without losing an appreciation of the inherent impossibility (perhaps even absurdity) of the managerial condition.