We present a novel framework for inspecting representations and encoding their formal properties. This enables us to assess and compare the informational and cognitive value of different representations for reasoning. The purpose of our framework is to automate the process of representation selection, taking into account the candidate representation’s match to the problem at hand and to the user’s specific cognitive profile. This requires a language for talking about representations, and methods for analysing their relative advantages. This foundational work is first to devise a computational end-to-end framework where problems, representations, and user’s profiles can be described and analysed. As AI systems become ubiquitous, it is important for them to be more compatible with human reasoning, and our framework enables just that.