Highly automated systems are likely to result in increased monitoring and supervisory control activities: the operator is placed in monotonous situations for long periods but he/she is required to be immediately alert and ready to make quick decisions if some critical events occur. In order to better understand the operator capability variations in complex environments the construct of “Situation Awareness” (SA) has been introduced. SA has been defined as the individual ability to (a) perceive elements in the environment within a volume of time and space, (b) to comprehend their meaning, and (c) to predict their status in the near future. However, SA theory development appears to follow many applicative requirements neglecting several basic aspects such as a clear definition of the cognitive processes engaged, and the standardization (or formalization) of elements, events, interactions, goals and behaviors leading to different degrees of SA. The aim of this study is to fill a gap in the literature in order to successfully understand the relationship between operators cognitive state, SA degree, modes of communication, and performance efficacy in teamwork. A computer game of strategy inspired by the board game Risk! will be used in the experimentation. The aim of the game will be to control armies in order to conquer and hold strategic (or functional) countries on the map. Participants will be assigned to teams and they will communicate from separated locations via “instant messaging” or “voice”. Two different levels of taskload will also be defined. Result will clarify: (1) the relationship between the cognitive processes engaged in different levels of taskload and the maintenance of appropriate degree of SA; (2) the teamwork behavioral strategies for reaching a shared goal; (3) the role of communication in the OFS variations and in SA sharing; (4) the role of geometrical/functional characteristics of the scenario (distance, color, etc.) on SA; (5) the possibility of integrating the individual SA measures in one team SA assessment (i.e., Shared SA). The emphasis of the current study is to provide a conceptual design of how the operator functional state should be represented and displayed in collaborative technologies aimed at improving the sharing of knowledge and awareness.