A new liaison role between Information Systems (IS) and users, the relationship manager (RM), has recently emerged.Accordingtotheprescriptiveliterature,RMsaddvaluebydeepunderstanding ofthebusinessestheyserve and technologyleadership. Little is known, however, about their actual work practices. Is the RM an intermediary, filtering information and sometimes misinformation, from clients to IS, or do they play more pivotal roles as entrepreneurs and change agents? This article addresses these questions by studying four RMs in four different industries. The RMs were studied using the structured observation methodology employed by Mintzberg (CEOs), Ives and Olson (MIS managers), and Stephens et al. (CIOs). The findings suggest that while RMs spend less time communicating with users than one would expect, they are leaders, often mavericks, in the entrepreneurial work practices necessary to build partnerships with clients and to make the IS infrastructure more responsive to client needs.