Parallel to the monumental problem of replacing paper- and pen-based patient information management systems with electronic ones is the problem of evaluating the extent to which the change represents an improvement. All clinicians must grapple with this daunting challenge; those with little or no informatics expertise may be particularly surprised by the attendant difficulties. To do so successfully, they must be able to explicitly conceptualize the daily clinical work - a prerequisite for appreciating and reasonably evaluating it. Further, few of these evaluators may have reflected on the dynamic interaction between their work and their tools - how changing a tool necessarily changes the work. This article illuminates these problems by telling the story of how one patient care information systems committee learned to think about, first, the purpose of a patient information management system and second, how to evaluate the impact of its implementation.