My son was like this — very skilled, but nervous. The answer was small group reps. He got into a small training group with bigger, older kids who played very physically. Playing 3 on 3 with big, aggressive kids totally cured him of playing hesitantly because there is nowhere to hide in 3 on 3, and it totally changed how his coaches perceived him. Having an aggressive attitude is a big part of basketball, and - within reason - makes other skills like shooting better , so if you can find small group training like that or an AAU team that specifically trains aggressiveness, it will help a lot.