Abstract. We discuss the motivation for a novel style of tutorial dialogue system that emphasizes reflection in a design context. Our current research focuses on the hypothesis that this type of dialogue will lead to better learning than previous tutorial dialogue systems because (1) it motivates students to explain more in order to justify their thinking, and (2) it supports students’ meta-cognitive ability to ask themselves good questions about the design choices they make. We present a preliminary cognitive task analysis of design exploration tasks using CyclePad, an articulate thermodynamics simulator [10]. Using this cognitive task analysis, we analyze data collected in two initial studies of students using CyclePad, one in an unguided manner, and one in a Wizard of Oz scenario. This analysis suggests ways in which tutorial dialogue can be used to assist students in their exploration and encourage a fruitful learning orientation. Finally, we conclude with some system desiderata ...