Our research work deals with the development of new learning environments, and we are particularly interested in studying the different aspects linked to users’ collaboration in these environments. We believe that game-based learning can significantly enhance learning and can also be used in industry. Although the students appreciate this approach, there is an obvious need for information about students’ skills, especially for the teacher. In our approach, the users may interact directly with each other and in the game with a professional business tool. These tools are equipped to be traced, and we can thus update the user model of the students when particular events occur, by using both data collected from traces resulting from the collaborative learning activity and information collected from the specific business tool integrated in the game. In this chapter, we focus on the teacher’s need for information when the students are using a specific but external professional business tool in the product lifecycle management domain. The “learning adventure” environment that we describe is a generic game-based platform allowing to set up a collaborative learning session with observation facilities of the system. The aim of this chapter concerns the application of such serious game environment to a concrete problem: to support organisational change in industry by helping to understand product lifecycle management (PLM). Real experiments have been made at our university in the PLM domain and in industry with the help of a company validating the feasibility of the approach.