This article describes techniques and strategies used to judge the potential applicability of new information management technologies in the clinical setting and to develop specific design recommendations for new features and services. We focus on a project carried out to identify the potential uses of handheld computers (i.e., the Palm Pilot or a small WinCE-based device) in the ambulatory practice setting. We found that the potential for a robust handheld computing device to positively affect the outpatient ambulatory clinical setting is enormous, and that the information derived from the exploratory research project is useful in creating specific design recommendations for further development.