To design interfaces, researchers in HCI have often set up ethnographic and ethno- methodological analysis of face-to-face situations that developers tried to emulate in on-line platform. Nonetheless, the observation of a group of designers producing an e-learning platform shows that this painting from nature/ after nature methodology is completed by a study of already mediated forms of interactions and representations of interactions. In design practice, the designer elaborates not only from the existing objects and ways of representing them, but also from the “interpretant”. Here, we observed how designers use and anticipate multiple semiotic literacies when they bridge from real life situation to a mediated situation. As the team designed an e-learning environment they realized that a virtual platform have to recreate the atmosphere of a class. To address this issue, they deployed a specific semiotic methodology that we called “contradictory semiotic analysis”. This methodology is based on a “dialog” between semiotic studies that balance the convergent effects of themes and the diverging effects of media. Here the expression “contradictory semiotic analysis” is used so as to illustrate the converging / diverging semiotic process that designers use to explore the expansion of a concept (here empathy) so that it can become operational in mediated interactions.