This sounds like the kind of thing that I struggle with, too. What I have done before, which you might want to try, is saying something like "I have this thing to talk about, but I am scared to bring it up" or "I know we should talk about X, but I don't really WANT to".

You could also straight out ask your T about this topic of bringing stuff up. I have before, but he still makes me do my own work most of the time :P