In recent years, research on IT usage has increasingly focused on post-adoption usage, rather than initial acceptance of a technology regarded as new. Consistent with this recent trend, we seek to understand what factors influence employees’ ongoing IT use and processes they rely on for expanding their knowledge and skills within organizational workgroups. Based on recommendations by Jasperson, Carter and Zmud (2005), we seek to understand feature-level IT use of office software applications that are most frequently used within four workgroups. We first document the knowledge and skills of each employee at the feature level. Second, we analyze detailed, feature level knowledge with a novel method based on Venn diagrams that reflects the degree to which coworkers have fully-, partially-, or non-overlapping knowledge and skills. Finally, we employ open-coding methods to identify enabling and inhibiting factors that shape the amount and effectiveness of IT-related knowledge transfer among coworkers. Our study yields surprising findings – including the fact that some employees have unique IT skills that do not overlap with their coworkers. Moreover, employees seek help from other workers who are at similar levels in the organizational hierarchy, and usually avoid seeking help from colleagues whose knowledge level is considerably higher, or whose knowledge base is radically different. Our results show that employees prefer to seek help from coworkers whose knowledge is similar to their own. We conclude by discussing the implication of our findings for managers and researchers.