He has the highest academic career at the workplace. So, I told him that he'll never need to be concerned about job-hunting. But, he said to me "I don't have an optimistic view on my job-hunting, because of my bad communication skill."
One of the problems is that most of the researchers around him have girl friends, which can discourage him to behave boldly. In fact, he has been blamed for not having any girl friend ever since by them.
What is needed for him to have self-confidence is to encounter as many people as possible. It must be chances to let him assume that he is superior to ordinary people.