Given a classification task, what is the best way to teach the resulting boundary to a human? While machine learning techniques can provide excellent methods for finding the boundary, including the selection of examples in an online setting, they tell us little about how we would teach a human the same task. We propose to investigate the problem of example selection and presentation in the context of teaching humans, and explore a variety of mechanisms in the interests of finding what may work best. In particular, we begin with the baseline of random presentation and then examine combinations of several mechanisms: the indication of an example’s relative difficulty, the use of the shaping heuristic from the cognitive science literature (moving from easier examples to harder ones), and a novel kernel-based “coverage model” of the subject’s mastery of the task. From our experiments on 54 human subjects learning and performing a pair of synthetic classification tasks via our teaching system, we found that we can achieve the greatest gains with a combination of shaping and the coverage model.