This article describes an investigation into the feasibility of using contextual reasoning to monitor and supervise the collaborative work of several knowledge workers working together on a project. Managing large and complex projects is a difficult task that requires situational awareness by the project manager to be able to be proactive when possible and to react correctly in the presence of events. In complex projects, effective oversight of the project personnel and the progress of the project are essential in ensuring that project objectives are met. This is especially true of projects that require contributions from various experts, whose interaction may be limited to a Web-based collaborative tool. Such oversight is typically the job of a project manager who is tasked with avoiding cost overruns, shipment delays, and ensuring product effectiveness. We utilize context-based reasoning and contextual graphs as the tools of choice for implementing an agent that emulates the function of a competent project manager. We use rocket design and manufacture as the domain to evaluate our technique. We use a public domain rocket design software package developed by the National Aeronautics and Space Administration as a guide to the domain. The article describes the investigation, its results, and the related works in a collaborative design project.