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