It has been suggested that iconic graphical signs evolve into symbolic graphical signs through repeated usage. This article reports a series of interactive graphical communication experiments using a ‘pictionary’ task to establish the conditions under which the evolution might occur. Experiment 1 rules out a simple repetition based account in favor of an account that requires feedback and interaction between communicators. Experiment 2 shows how the degree of interaction affects the evolution of signs according to a process of grounding. Experiment 3 confirms the prediction that those not involved directly in the interaction have trouble interpreting the graphical signs produced in Experiment 1. On the basis of these results, this article argues that icons evolve into symbols as a consequence of the systematic shift in the locus of information from the sign to the users' memory of the sign's usage supported by an interactive grounding process.