The research reported in this paper is based on the argument that organizational information systems as we currently build them tend in most cases to disappoint. This happens because they are inflexible artifacts whose purpose is to model dynamic organizations. Our objectives are to find better ways of thinking about change and adaptation of information systems within organizations by exploring the concept of 'fit'. The degree of fit between a given organization and a given information system can be judged subjectively, but currently there exists no measure which is general useful and objective. There is also no research that identifies what criteria people use when they make these subjective judgements. Our endeavours focus to determine what the barriers to such knowledge are, and to develop a generic framework for acquiring and maintaining such knowledge in any desired context.