An important condition for serving the educational objectives of simulation-based team training is that the facilitator’s instructions during the briefing bridge the gap between the simulation and the clinical situation it is intended to represent. This chapter unpacks instructional challenges in briefings by focusing on how instructors make use of trainees’ exhibited understanding of tasks to demonstrate how procedures should be adapted to the specific conditions of the simulation. Further, the chapter addresses the interplay between the simulation scenario, the provision of manikin features and the instructor’s guidance in the scenario and the relation to team performance in the simulation. The chapter shows how additional information is conveyed to the participants during the scenario to overcome the shortcomings of the simulator and how the sequencing and timing of this information during the scenarios were crucial for furthering the participants’ activities.