Once the skill is performed accurately and independently under one condition, are you arranging multiple opportunities for the student to practice the skill with different people, and in multiple settings?
With this particular skill, it will be very important to practice both with a variety of people and across a variety of contexts. First, teach and practice the skill with a familiar instructor. Then, continue practicing with various familiar people, such as family members, friends, ’safe’ peers, etc. Finally, arrange opportunities for the student to practice the skill with less familiar people so he becomes more comfortable with reciprocity within increasingly unpredictable exchanges.
Secondly, make sure you are practicing reciprocal conversations across a variety of conversation topics. For some students, it would be appropriate to start the teaching process with preferred topics that the student chooses. Then, move towards less familiar topics, as well as topics that the instructor selects. Make sure the student is still able to comment, ask questions, and adjust to topic, even when it is not a topic of strong interest to them.
However, if the student tends to monologue about a high interest topic, this might not be the place to start because reciprocity might be more difficult to achieve. In that case, begin with topics that are of neutral value to the student.
Are you arranging opportunities for the student to practice the targeted skill in natural environments and under natural conditions?
Review strategies before the student goes to class or work, and then encourage him to hold a conversation with someone else, using their newly learned skills. It will help to observe them so that you can provide feedback. If you are not able to observe them, or if it makes the conversation less natural, perhaps you could obtain feedback from their conversation partner (if appropriate) or from the student himself.
Have you adapted visual supports so that they can remain in the natural environments that this student encounters now, and in the future?
Are you collecting data to make adjustments to your teaching and to ensure that the student is performing the skill across multiple conditions?