The dominant rational approach to IT-centered strategic change derives from the positioning literature in business strategy. It assumes a single best path to successful organizational transformation. Three cases are used to show that,inpractice,therearemultiplealternativepaths. ThestrategicITandbusinessstrategyliteraturesarecritiqued in terms of the process of fit so as to explain why these alternative paths are successful. Two distinctive characteristics of the fit process -- the search for simplicity and differential risk management profiles -- are identified. Their roles in successful paths are discussed.