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When people engage in conversation, they tailor their utterances to their conversational partners, whether these partners are other humans or computational systems. This tailoring, or adaptation to the partner takes place in all facets of human language use, and is based on a mental model or a user model of the conversational partner. Such adaptation has been shown to improve listeners' comprehension, their satisfaction with an interactive system, the efficiency with which they execute conversational tasks, and the likelihood of achieving higher level goals such as changing the listener's beliefs and attitudes. We focus on one aspect of adaptation, namely the tailoring of the content of dialogue system utterances for the higher level processes of persuasion, argumentation and advice‐giving. Our hypothesis is that algorithms that adapt content for these processes, according to a user model, will improve the usability …