Assisting teams of knowledge workers achieve common strategic and tactical goals is becoming an increasing priority as information analysis tasks become more complex. Tools to monitor and support individual workers, such as TaskTracer, demonstrated the potential for assisting individuals but there is a lack of tools for analyzing workflows and information needs at a collaborative level within enterprises. Providing assistance for collaboration is a current priority for the new generation of ‘smart digital assistants’ and presents unique challenges, in terms of associating collective goals with user activities in way that minimizes disruption to the user's workflow, and in generating useful summaries. To address these challenges, we have developed ‘Journaling’ interfaces to: capture a user or team's tasks and goals, associate them with information artifacts, assist in information recall, and display aggregate visualizations. These interfaces are supported by a passive instrumentation platform that aims to monitor user's consented activities in a minimally intrusive manner, including interactions with various applications, documents and URLs as part of collaborative workflows. We have deployed these interfaces in a production environment using heterogeneous workflows performed by groups of students and intelligence analysts. Evaluations based on user interviews and engagement metrics suggest that our approach is useful for understanding and supporting user collaboration, as well as being easy to work with and suitable for continuous use. In addition, the data gathered provides situational awareness for individuals, teams, educators and managers. Through our platform, we are enabling continuous collection of labelled user activity logs and document corpora that are enabling further research in this nascent field.