This paper challenges the view of transformation in organisations as a discrete activity with pre-determinable outcomes. Instead, drawing from the dramaturgical perspective, it is suggested transformation, including organisational development, might be better understood as an ongoing series of open-ended dialogic performances filled with ambiguity. Using a selection of ethnodramatic data generated in a collaborative research partnership with a supplier to the New Zealand construction trade, this paper offers a new participatory methodology, organisational playmaking, for both researching and enacting organisational transformation. It responds to calls for empirical research into the "how" of development by drawing out connections between theatre, organisational research and the associated aesthetic pedagogy of play, including links to flow, framing and "communitas". In particular it pays attention to how the identities and intentionalities of all those involved in organisational transformation - including external parties acting as "developers" - are multiple, partial, transient and subjective. In so doing, it claims all participants engaged in such methods must be willing to contribute to and be changed by the collectively constructed performances of organisational transformation.