What are some reinforcing consequences you can deliver either immediately following the desired behavior or following a practice session– things that this particular student enjoys, wants, seeks out, etc.?
Are you using labeling and social praise to make the contingency between desired behavior and reinforcing consequence clear to the student?
During initial instruction, are you providing consistent feedback to reinforce skill development? It is important to choose friends and familiar people who will respond supportively during practice sessions.
What reinforcing consequences can you arrange that are more naturally or intrinsically connected to this targeted behavior?
At the end of the conversation, does the student feel like it was a success? Depending on the situation, can the conversational partners give the student positive feedback on his performance?