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This paper builds on the principles and insights from improvisational theater to unpack the nature of collective improvisation and to consider what it takes to do it well and to innovate. Furthermore, we discuss the role of training in enhancing the incidence and effectiveness of improvisation. We propose that two common misconceptions about improvisation have hindered managers' understanding of how to develop the improvisational skill. First, the spontaneous facet of improvisation tends to be overemphasized, and second, there is a general assumption that improvisation always leads to positive performance. Our goal is to clear up the conceptual confusion about improvisation by laying out the various aspects of preparation that are required for effective improvisation. In our theoretical model, we delineate how the improvisational theater principles of "practice," "collaboration," "agree, accept, and add," "be present in the moment," and "draw on reincorporation and ready-mades" can be used to understand what it takes to improvise well in work teams and to create a context favoring these efforts. Our findings support a contingent view of the impact of improvisation on innovative performance. Improvisation is not inherently good or bad; however, improvisation has a positive effect on team innovation when combined with team and contextual moderating factors. We also provide initial evidence suggesting that the improvisational skill can be learned by organizational members through training. Our results shed light on the opportunities provided by training in improvisation and on the challenges of creating behavioral change going beyond the individual to the team and, ultimately, to the organization.