There is an extensive body of work on Intelligent Tutoring Systems: computer environments for education, teaching and training that adapt to the needs of the individual learner. Work on personalisation and adaptivity has included research into allowing the student user to enhance the system’s adaptivity by improving the accuracy of the underlying learner model. Open Learner Modelling, where the system’s model of the user’s knowledge is revealed to the user, has been proposed to support student reflection on their learning. Increased accuracy of the learner model can be obtained by the student and system jointly negotiating the learner model. We present the initial investigations into a system to allow people to negotiate the model of their understanding of a topic in natural language. This paper discusses the development and capabilities of both conversational agents (or chatbots) and Intelligent Tutoring Systems, in particular Open Learner Modelling. We describe a Wizard-of-Oz experiment to investigate the feasibility of using a chatbot to support negotiation, and conclude that a fusion of the two fields can lead to developing negotiation techniques for chatbots and the enhancement of the Open Learner Model. This technology, if successful, could have widespread application in schools, universities and other training scenarios.