Young adults with autism spectrum disorder (ASD) typically benefit from individually-designed interventions to engage in reciprocal conversation. We used a multiple baseline across participants design to evaluate the effects of a technology-based self-monitoring application (i.e., I-Connect) and visual supports to teach question asking skills to three males with ASD, ages 21-26. Participants selected community locations to participate in structured conversations with peers that were audio recorded. All participants demonstrated an immediate effect to increase their number of questions asked when using I-Connect to self-monitor. However, participant responding varied when visual supports were added. Maintenance also varied across participants. Findings indicated existing evidence-based practices for learners with ASD, such as self-monitoring and visual supports, can be combined in socially valid ways. Implications and suggestions for future research related to teaching conversation skills for young adults with ASD are discussed.