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This study presents an analysis of a tool that supports collaborative reflection at work. So far, research has focused on individual reflection or reflection in an educational context. Therefore, little is known about designing support for collaborative reflection at work. In four studies that use an application for collaborative reflection support, built based on prior empirical work, the paper presents an analysis of the ways workers used the tool for collaborative reflection. The analysis was based on log data and material from interviews and observations. The results show that there were different ways in which people used the application and that the impact of using it differed among groups. Besides positive effects, open issues in reflection support emerged. The paper presents insights on and design challenges for collaborative reflection support and potential solutions for these challenges. The findings are related to a model of collaborative reflection support and they emphasize that such support needs to be understood as socio-technical in nature if it is to succeed in practice. Finally, the study proposes designs for further work on tools supporting collaborative reflection.