The greatest confidence builder to me was actually playing before an audience. The more that I did it, the more confident I became. Even though my skill level wasn't that great I began to feel comfortable that I would be able to play adequately, and my nervousness diminished
I also was more confident when I had practiced the material that I was going to play until I knew it upside down and backwards.
Bottom line is he has to jump in the water with both feet, but he has to be able to swim some.
berbie