Supporting users’ training and thus improving their working productivity by increasing their search performance is crucial in every day’s work-life. This holds true not only for knowledge workers like auditors, who needs to stay-up-to-date with law and new compliance regulations, but also for production workers who need to improve their IT skills in order to keep pace with new technologies established within the ongoing digitalisation in Industry 4.0 (Kleindienst et al., 2016). In both settings, there is a substantial need for workers to find work-related relevant information at the right time. To achieve this, especially production workers with low IT literacy as well as auditors, who need to keep track on the continuous change of laws and rules, need informal learning opportunities on how to improve their search capabilities during their daily work. In this work, we present a first design concept of an adaptive and reflective training support widget. The widget aims at supporting workers to train new search functionalities in order to enhance their search productivity during work.