Is English not his first language?

"he does work for" means what? With only the ITIN, he would not be qualified to work for them. To work for them, they would be asking for I-9; is it possible that might have sounded somewhat like FIAN to him?

"He ask me if he should or not."

Because we know there is something a bit shady with their relationship and want to skirt the requirements knowingly?