The agricultural production industry faces a fundamental transformation towards highly automated machines and operation procedures. Introducing swarm-based robot systems for processes such as soil cultivation, sowing, and harvesting comes with new operation scenarios requiring operators to monitor several machines simultaneously. Conventional user interfaces may not be able to cope with the associated change in information and interaction requirements. However, a successful transformation towards such automation scenarios depends on a suitable interaction design that considers human factors such as situation awareness, trust, mental models, and workload. Through efficient navigation architectures or visualisation techniques, user interfaces can counter the impeding effects of humans being out-of-the-loop in multi-robot represent a promising approach to address these issues. Instead of function-based information presentation in conventional user interfaces, goal-oriented approaches highlight the role of machine functions and states in the context of higher-level performance goals. This approach provides opportunities to support operators in understanding the underlying relations between machine functions and their effects on goals such as production performance or efficiency. This article presents the development and evaluation of a goal-oriented user interface for monitoring and controlling highly automated combine harvesters. A hierarchical information visualisation summarised machine data into high-level performance indicators. This visualisation approach also enables operators to access information and control options at different levels of depth to facilitate their situation assessment efforts in continuous switching of loops in multi-robot monitoring. However, fundamentally changing visual and functional characteristics of user interfaces may contradict performance, as they require operators to adapt. A good fit to the operators’ mental models of high-level processes is required to achieve acceptable levels of intuitiveness and acceptance. To evaluate this alternative approach to user interface design, we observed experienced and novice operators working with a functional and interactive prototype and measured perceived usefulness, usability and user experience.