We taught three high school students with high-functioning autism to increase their novel peer-directed questions when using a communication book to converse with general education partners at school. Novel question training was associated with participants asking peer-directed questions not displayed in communication books across a variety of conversational partners. Partners systematically responded to questions participants asked throughout the study, whether questions asked were displayed in participants' books or not. In addition, partners' initiations to participants increased when participants asked more peer-directed questions not displayed in their books. Social validation data gathered from participants and partners generally confirmed the importance of the study's goals and outcomes; normative data indicated that participants engaged in conversation in a fashion similar to their general education peers. Findings are discussed with respect to future research and practice.