My T is quite straightforward, thankfully. When I don't understand something he said, I don't think he's trying to be oblique, but just maybe stated it unclearly. Alternatively, my brain was mush that day, and the comprehension problem is on my end. If I don't get something he says, I just ask him what he means, and he clarifies. I've gotten really comfortable doing that with him. It's so much easier than just assuming I get what he is saying when I'm not sure, or trying to read his mind.