I went through this few years ago in Calgary, started on weekends in SE industrial area on really quiet streets. If you go through basics really slow and manage to explain that you would rather live a boring life for 40 more years than enjoy him playing NASCAR racer for 2 minutes - it's manageable.
Then we slowly progressed to "commentary drive" on quiet streets and than to switching places when we were just going somewhere.
The hard part is staying (mostly) positive and never letting your guard down, staying alert and thinking ahead of what can go wrong, because it will try to go this way at times.
I had to pass ~50 driving tests for QHSE people some time ago and felt safer if I was teaching him, so I didn't hire anybody. I also made him watch "Defensive Driving" DVD few times.
It worked ok - he passed the first time and seems to be pretty responsible driver.
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