Based on my experience, I would say that if you're experiencing tentativeness on his part, then he is not up to the task -- and may have a hard time knowing why. For me, it's been a negative transference that no therapist could help me resolve. It's "good", in a way, for me to feel all the negativity and rage which I had cut off -- but without some other kind of "holding" environment -- can be bad news, I think. I've been having a really hard time with mine.