Due to the introduction of highly automated vehicles and systems, the tasks of operators (drivers, pilots, air traffic controllers, production process managers) are in transition from “active control” to “passive monitoring” and “supervising”. As a result of this transition, the roles of task load and workload are decreasing while the role of the mental load is increasing, thereby the new type of loads might be defined as information load and communication load. This paper deals with operators’ load monitoring and management in highly automated systems. This research (i) introduces the changes in the role of operators and requirements in load management, (ii) defines the operators’ models, (iii) describes the possible application of sensors and their integration into the working environment of operators, and (iv) develops the load observation and management concept. There are some examples of analyses of measurements and the concept of validation is discussed. This paper mainly deals with operators, particularly pilots and air traffic controllers (ATCOs).