This chapter explores the role of those shaping engagement largely in the frame of rhetoric and design. In the frame of design, all participants in social interaction are positioned as both rhetors and designers, even if differently so. Design is a social semiotic category, which one uses to describe how sign-makers construct social environments for themselves and for others in their communities. In a social semiotic framework, the relation of instructor/teacher/trainer on the one side and learner/student/trainee on the other is a specific instance of the vastly encompassing general social relation of rhetor and audience. The examples discussed in this chapter show two of the different environments that medical trainees move between the operating theatre and the simulation environment and there are many more, including online discussion forums, virtual learning environments, lectures and meetings in corridors. Online platforms are extending the range of kinds of learning environments that learners can choose to engage with.