Abstract: The future deployment of single pilot operations must be supported by new cockpit computer services. Such services require an adaptive context-aware integration of technical functionalities with the concurrent tasks that a pilot must deal with. Advanced artificial intelligence supporting services and improved communication capabilities are the key enabling technologies that will render future cockpits more integrated with the present digitalized air traffic management system. However, an issue in the integration of such technologies is the lack of socio-technical analysis in the design of these teaming mechanisms. A key factor in determining how and when a service support should be provided is the dynamic evolution of pilot workload. This paper investigates how the socio-technical model-based systems engineering approach paves the way for the design of a digital assistant framework by formalizing this workload. The model was validated in an Airbus A-320 cockpit simulator, and the results confirmed the degraded pilot behavioral model and the performance impact according to different contextual flight deck information. This study contributes to practical knowledge for designing human-machine task-sharing systems.