Impairments in social communication are one of the defining characteristics of individuals with autism spectrum disorders (ASD). However, there are only a handful of studies that investigate interventions to improve social conversation skills in adolescents with ASD. To address this gap in the literature, this study investigated the outcome of a self-management intervention to ask on-topic questions during naturalistic social conversation. To examine the effect of this novel intervention, a non-concurrent multiple baseline across participants design was employed. Three adolescents with ASD, ages 12, 13, and 15, participated in this study. The data supported that with intervention, the participants were able to increase the number of questions they initiated in conversation and improved in their ability to use question-asking to maintain a single topic of conversation. The intervention also resulted in a substantial increase in the percentage of participant utterances that contained a statement or question that maintained the topic and continued the conversation. Additionally, the participants decreased their use of minimal responses during conversation, suggesting that the participants were able to play a more active role in the conversation. Support for fading of the intervention and generalization to new conversational partners was found. Lastly, results from a social validity measure indicated that there were widespread gains in global pragmatic behavior when comparing conversations at baseline and generalization. The findings are discussed in relation to theoretical implications and clinical significance.