Offshore activity is developing and resulting in new demanding high-risk operations. Operation complexity increases with factors like heavier loads, subsea installations, and arctic waters; operational planning requirements increase as well. Demanding offshore operations are usually planned in detail, where plans may fill several binders, leading to information overload for the ship crews. Extracting critical information becomes a challenge. In some cases, only a basic plan exists, and aborted operations are quite frequent, also where a contingency plan could have enabled recovery. This results in substantial extra costs for the operating company. The industry is facing two key challenges concerning operational planning. One is to develop good planning frameworks, to enable plans with robust risk management and control. This calls for modelling techniques for operational plans. Another is optimal presentation of the plan for each individual crew member, both in the briefing and in the execution phase of the operation. It is important that every individual has easy access to the most relevant and safety critical information for his given role and the current situation, in an easily accessible and comprehensible format. This calls for operational software to support situation-awareness. A fundamental necessity to achieve this is modelling techniques which support a joint understanding of the operation between operational planners, ship crew, software engineers, and ultimately the support software. In this paper we show how to translate hierarchical task analysis (HTA) models into software models and then into situation-aware software prototypes.