In the past few years, Reduced Crew Operations (RCO) represent an inevitable as an unavoidable development for the aviation industry, and as such a major challenge for pilots and airlines. It is justified for us, researchers, to address the potential shortcomings of such a development. Over the course of their professional life, pilots might face incapacitation, which may be temporary or permanent, partial or total, coming from cognitive overload, stress, loss of situational awareness (SA), or anything else impairing their ability to carry out their missions. Up to now, the risk of pilots’ occupational incapacity has been addressed by the presence of a copilot in the cockpit, able to take over if necessary. Following this reduction in aircrew, the next step is placing a pilot alone onboard to manage the activities of the crew (case of Single Pilot Operation). It is thus fundamental to design a virtual assistant in order to support the capacity of efficient and relevant knowledge transfer. It is therefore necessary to be able to transfer knowledge of the context to a pilot replacing the one in a state of incapacitation.Since our study is rather explorative, the authors could not cover a whole flight mission. Therefore, this study focused on the landing phase. We placed particularly emphasis in our research on the study of the pilot’s cognitive models such as SA, operational strategy and decision-making. We investigated the inherent behavioral elements to design a decision model adapted to the variability of the pilot’s profiles. Afterwards, we designed a test bench and presented a use case to eighteen pilots from different companies with a representative set of individuality. For this purpose, we placed those pilots in a flight simulation during a complex scenario involving an aircraft failure during a landing phase with bad weather. At the end of the scenario, we asked pilots to go through their experience in the simulator to understand their situation awareness. These situation awareness requirements gave us clues with regard to the pilot’s perception of salient information about the cockpit environment, and the context associated with the situation.This explorative study highlighted the need for understanding how pilots share their knowledge to another pilot. By doing so, we aim to develop a generic methodology of selection of the useful and necessary information to share with an operator in a complex situation.