If I were a single man dating now, but knew everything I know about life and marriage, I would ask a woman I dated lots of questions, direct the conversation to cover certain topics. But when I was single, back when I was young, I wasn't nearly that meticulous or detailed. Actually, I did have a fair amount of criteria. Looking back over a journal, I see I was getting some answers when I dated the woman I married and I had reasonably good criteria for a young man.
But I didn't know how many children I wanted to have, and didn't ask the woman I would marry. She wanted to have children. That was enough for me.
I wouldn't be too hard on the guy because he isn't a good interviewer. Maybe he thinks he'll learn enough about you through osmosis, or through organic conversation without having to probe and pry too much. He may not know the questions to ask. That is the case with a lot of younger men. If you haven't been married, you may not know the questions to ask. If you are young, you may not know the questions to ask. That's the irony.
I think it is better to ask questions, especially about deal breakers, before the relationship goes on too long. That way, if you hit a deal-breaker, you break off the relationship before either party gets too hurt or too invested.