Intelligent systems in everyday lives learn about their users to tailor services over time. However, these systems are often designed with little consideration of user agency on their learning processes, hindering users from taking full advantage of the systems. In this paper, we propose Teaching-Learning Interaction (TLI) as a new form of interaction that affords user agency by letting users reflectively shepherd an intelligent system’s manner of learning. Given such agency, users will be able to better personalize services for themselves. We first draw on Schön’s notion of knowing-in-action and reflective practice to theoretically ground our concept. We then present the resulting definition of TLI and three design qualities, which are further concretized with three design examples. We end with discussion on the implications of TLI for HCI design.