The use of characters to present tasks and critical information in a simulated environment has proven to be a useful strategy in the creation of more authentic learning environments online. Such characters can not only perform the role of setting and structuring tasks within the fictitious scenario, but also that of providing useful and realistic guidance. This chapter describes a learning environment designed to create an authentic context for learning evaluation skills and strategies appropriate to technology-based learning settings. The subject in which this approach was adopted was a masters-level course in evaluation of technology-based learning environments. The chapter focuses on the use of a fictitious CEO (chief executive officer) who requests certain evaluation tasks of “employees.” Students are given realistic jobs with realistic parameters, and in this way the subject is dealt with in a much more authentic manner than if presented in a more decontextualised way. The rationale for adopting the approach is described together with a description of how it was implemented and summary findings of an evaluation of the approach.