It is not a cliche to say that females are communicators in our culture, and males generally are not. It's especially difficult to get a boy to open up about what's troubling him; a typical response is "I don't know."
Adam Cox is a psychologist and author who has put a lot of work into communicating with boys. He offers perceptions and practices in the book Cracking the Boy Code: How to Understand and Talk with Boys.
Dr. Cox visited in 2018, and we revisit the interview here.