ICT tools offer the possibility to store, analyse and visualise large amounts of educational data. However, in order to make sense of these analyses, teachers need meaningful information connected to their pedagogical intentions. We envision an enriched learning-design process, which supports the integration of the issues related to monitoring in the script. This paper presents a study where the first author and a teacher iteratively co-designed two authentic learning scenarios with the aim of defining and evaluating a monitoring-aware design model and process. These two proposals, the model and the process, were positively evaluated by the participant teacher, and are the basis for the future implementation of an authoring tool that will support the proposed monitoring-aware design process.