The tools and artefacts are increasingly interpreting various issues for humans. The tools may display interpretations of what we should read, view and listen or how we should understand the moods and emotions of others or what might be the “best” actions for us to take next in our life. Distance work collaboration is seen to be enhanced by virtual reality solution. Often it is hard or impossible to know how the suggestions and interpretations have been created. Should designer understand the technological solution operating in the background, should the machine learning interpretation process be opened to the users of the tools and artefacts? Some tentative answers can be found from the new understanding of perception, namely, the relation between organism and affordances as well as on understanding meaning creation as being part of various dynamic systems. The research on radical embodied cognitive science combined with Gibson’s ecological psychology and pragmatism allows to ponder on the responsibilities designers have when designing tools and artefacts – how might the systems change with the introduction of the new tools. In this paper, I will discuss affordances as dynamic relations between organism abilities and environment features. How the new understanding of affordances fits with pragmatism and what the notion of semiosis and habit formation will bring into the dynamic system view. The dynamic view of the system and the direct interaction with environment will help to consider how designers might approach the responsibility of potential changes in the system that the new design will bring along. The radical cognitive science and pragmatism will aid to see potential challenges that virtual reality solutions and artificial intelligence interpretation will pose. Some of these challenges as limited direct interaction with the environment hamper human perception and knowledge construction.