Training based on Virtual Reality (VR) has reached a level of maturity that renders it applicable in many industries. By moving through learner interaction and representational fidelity, from navigable to interactable VR learning environments, the relationships between trainees, VR technology, and the world that trainees experience change. These relationships are central to the theory of technological mediation. In this theory, the central idea is that humans' perceptions and interpretations of reality are transformed when the latter are mediated by technology. Using this theory, the objective of this study is to provide insights into the different roles that mediation, in the relationship between trainees or users of this technology and construction practice, may play in the new type of context-realistic VR learning environments. To this end, the development of a framework for generating an innovative VR tool for training operators on construction sites was chosen as the subject of a case study. By focusing on the development phases of this framework one is able to scrutinise the underlying elements that shape the changing relationship between trainees, the VR environment, and the real world.