Software that intelligently interprets the goals and needs of its users on the basis of their behaviors without interrupting the work flow and consequently disturbing concentration and software that can support the users in a personalized, smart, yet unostentatious way is a desirable vision, for sure. One attempt to such support system was Microsoft's famous paperclip. The underlying logic, unfortunately, was rather simple and the users did not accept the feature very well. This paper introduces a psychologically and formally sound approach to a non-invasive, hidden assessment of very specific needs of the users as well as their competencies and corresponding tailored support and feedback. The approach was developed in the context of adaptive digital educational games and is based on the concepts of Competence-based Knowledge Space Theory as well as that of Problem Spaces. The purpose of this paper is to broaden the concept and elucidate a possible bridge from computer games to regular software tools.