[the Obscure]

I think the role playing will be really helpful, especially if you push to get him out of his comfort zone (not in a mean way, of course). From what you said, he seems more relaxed when he's speaking to you, probably because he knows that if he makes a mistake, it won't be a big deal. But when he's working, he's probably pretty nervous that if he makes a mistake, it could hurt his job - maybe he won't make a sale, or he'll lose a client, etc. When you're creating a situation similar to his work environment, keep him on his toes and make sure he doesn't see you as the teacher he is comfortable with, but a client that makes him nervous.

Another thing you could do is make a cassette that drills the vocabulary that he'll regularly need to use. I know that drilling totally sucks, and isn't any fun at all, but it's one of the best ways to learn fluency in a language.

So, for example, if your student works at a clothing store, you could drill stuff like, "Hi, can I help you?" "Would you like to try that on?," etc. First, you would record yourself (and a friend if you can scrounge one up) having a typical in store conversation, such as (and this is totally lame, but it's just to use as an examle):
A: Hi, can I help you?
B: Yes, where can I find the jeans?
A: There right over there, next to the shirts.
B: Thanks.
A: Let me know if there is anything else you need.

That way he can hear what the conversation would normally sound like.
Then you go in for the repetition:
Can I help you?
(pause for about 10 seconds)
Can I help you?
(pause)
Hi, can I help you?
(pause)
Where can I find the jeans?
(pause)
Yes, where can I find the jeans?
(pause)
Next to the shirts.
(pause)
Next to the shirts.)
(pause)
They're right over there.
(pause)
They're right over there.
(pause)
They're right over there, next to the shirts.
(pause)
Thanks
(pause)
If there is anything else you need.
(pause)
If there is anything else you need.
(pause)
Let me know.
(pause)
Let me know.
(pause)
Let me know if there is anything else you need.

So, he'd be focusing more on repeating what he would typically be saying, but he would also be saying what his customer would say, too. This will help familiarize him with both sides of the conversation.

He can take the tape home with him, and you could ask him to try to practice once (or even twice) a day for 10 minutes or so. Eventually after he practices enough, he'll start to say the phrases without really thinking about them. They'll become a natural part of his speech. But when he's doing this, it's important that he's not reading anything. He should only be listening and repeating.

It might be a lot of work to make, but it would probably be a pretty useful resource.

Anyway, good luck!

The O