Risk is a multidimensional notion in any industrial sector and society depends on the actors involved, social-economical factors, complexity and nature of the technology and the safety culture of the environment in which its operates. Risk, as an aspect in decison making in operator tasks, is also multidimensional. Accident analysis in various fleet segments in the maritime industry demonstrate that a specific approach to risk decision making is required to fully understand the nature of the decisions and risk perception of the operators. In additon to the traditional frequentistic approach, die use of a scenario approach could improve the identification of typical events, taking into the culture and context in which they occur. Such an approach could lay the basis for adaptive automation and knowledge based training of operators to improve their problem solving capacity and to enhance their risk decision making processes.