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Focus on the external. Keep the focus on the external until the conversation feels natural, and he becomes more animated. Engage him in activity. Transition the conversation to the personal.
Shy people tend to focus on the self and feelings of inadequacy. By diverting attention to the external, he may become less guarded and communicate more freely. Feelings of shame will increase shyness. Discussing events or subjects related to the environment decrease the likelihood of unintentionally shaming him. Shy people are very self-aware and often avoid making large hand motions and facial expressions in uncomfortable conversations. Increased use of gestures and facial expressions may be an indication of decreased self-awareness. Getting too personal too quickly may cause him to become overwhelmed and emotionally detach. This is particularly useful when the conversation doesn't feel very natural. Working on something together will establish a structured flow of communication, reducing the pressure of figuring out what to say and when. Playing a game is a great way to focus attention externally. For example, you might ask, "Do you want to play a game to help pass the time?" He will likely ask what game, so be prepared to answer. If he recommends a different game, don't worry about not knowing how to play. Instructing you how to play the game is a great opportunity for him to become comfortable with the dialogue. Only attempt this after the communication becomes more natural and maintaining conversation requires less effort. You'll know you've reached this point when you realize the conversation has been flowing for several minutes without thinking about how to keep him talking. A good question to get him talking about himself is "How do you like to spend your free time?" You can then follow this up with questions about what he enjoys about his pastimes. If he seems resistant, revert to the external and try to transition again after he appears comfortable again. If you haven't been able to make the transition after a few attempts, tell him you've really enjoyed the activity and schedule another a time to play again. This will give him additional time to become comfortable with your interactions.