I have a player who is going into the 9th grade this year. He is 6'4'' and the doctors have told him he will most likely be 6'8'' or 6'7''. He is a very good basketball player for his age, but all he has ever been taught has been how to play down low and not been taught well. He has shared interest in maybe playing beyond high school, and I have told him he is, or will be, about SF size. I'm having a difficult time getting him to play from the perimeter. I have told him to work on his ball handling and shooting. My question is... What can I do to move him along in the progression of getting him to be more comfortable playing outside? Also are there some good drills or tips I can give him to improve his game? I only see him once a week for an hour, but I want to help him... Thank you in advance!

Just put him on the perimeter. Then help him work on his ballhandling, perimeter moves, and shooting.

I would teach him the post moves in this ebook because those same post moves work exactly the same on the perimeter. I'm not sure why more coaches don't simplify things and teach everyone the same way. It works great.
http://www.breakthroughbasketball.com/pr/post-play.html

Have him do some ballhandling drills:
http://www.breakthroughbasketball.com/drills/basketballdrills.html#ballhandlingdrills

Then throw him into competitive ballhandling drills:
http://www.breakthroughbasketball.com/fundamentals/missing-link-player-development.html

The competitive drills are the key. Why are point guards so good with the ball and comfortable under pressure? Because they've been forced to handle the ball in competitive games for how many years? When put in competitive situations, players adapt and learn quickly. We also have a new DVD coming out in 3-6 weeks that has a bunch of competitive drills that will really help with the development.

Thanks a lot Jeff!

Another good drill is the 55 second garden glove drill:http://www.youtube.com/watch?v=bMaXO5WuxFA

I do this w/ my 8th graders and one of my big guys (6') has the record on our team for the fastest time.

I would recommend doing some full court two-ball dribbling drills. They don't take long, but you can have them dribble through cones and make a lay-up on the other end while not losing the other ball. Come back and do it the other way. You can mix it up with dribbling at the same time, machine gun dribble, behind the back once, etc.

There are tons of dribbling drills if you search YouTube. Gannon Baker has lots, there are dribbling drills w/ tennis balls that are really good, but in the end, this big guy will have to work on his own everyday for 15 min. Something as simple as 50 dribbles each for both hands, low, high, push/pull side, push/pull fwd & back, and then behind the back. Ultimately, he would do this with eyes closed or blind folded.

I agree with Jeff on the competitive drills, especially the drills that have some type of record to break. Most of the kids come back to the next practice wanting to beat the old record, which means they have to practice on their own before the next practice.