I feel like my players ask the wrong questions. For example thy went to the strip club, they're trying to hunt a vampire who they "know" came south from Chicago. Their questions aren't necessarily wrong, but they don't ask the right ones, or the right people. When they went to the club they talked to the General Manager and asked him "if there were any new players in town", not a bad question, but he and almost no one else in the club knew anything about that.
Every stripper that came over they sent away except for one whom they asked the same wrong question. One of the girls that came over actually knows the vampire they're looking for. The one they talked to is the demon I've been asking about, but it was only a minor conversation and every time she tried talking to one of the characters they he told her to get lost.
So what're the right questions in my mind? "who else might know?" would have been one, or even asking about players in the criminal space (would have lead them to a werewolf pack that runs a gang). Giving any of the people they're talking to anything to go on besides the appearance of the vampire would be another. Actually talking to the people around about things at all.
Another part of the problem is that this is actually good role playing, the man that lost his wife and daughter is essentially playing an angry drunk. Outside of a stint in prison none of them are actually involved in the criminal element so it's not expected that they'd know much.
I sometimes have them roll wits + intelligence where I replace their brains, if they succeed I tell them the question they should be asking themselves given what's in front of them.
update it might be worth saying this, I had 4 different characters in that one scene with different information, because the characters are human, and only 1 of those 4 was, they would not necessarily be forthcoming (for example with the vamp it'd be a masquerade violation, and an outing of a covenant member). I had another 2 directions they could have gone, and all of these directions lead elsewhere. They only decided to pursue talking to the person that is currently possessed by the Strix after encouragement from me. They only decided to pursue the tabloid publishing of the Strix after, which was from a CCTV that they thought only they and one other person had seen after I made them roll and told them, that it occurs to them to wonder how the picture got in the tabloid in the first place (I had told them when I dropped the tabloid that it was a still from the camera). Otherwise they weren't going to bother following up on that. I'm mentioning this because I don't think that it's because I'm not giving them clues or having enough of them at this point.
How can I get them asking the right questions without my leading them around by the nose?
update though tangentially related the problem, my plan moving forward is that a Strix picture got into a tabloid, with the obvious Masquerade violation, the Vampires in Austin are going to be doing everything possible to torch it.
Best Answer
The answer to this depends on your playstyle - but you don't have the problem you think you have. Observe:
If you run a simulationist sandbox-y style of game, where you don't require your players to achieve anything in particular for you to consider the game a success, there are no wrong questions. There are questions that don't get the players the answers they were looking for, and there are questions that do - but in either case, you needn't care; The game will continue, and be fun, whether or not the players find the bloodsucker in question.
If you run a railroad with a fixed destination and you need the players to get this information in order to continue to your next dose of plot, there are no wrong questions. Just ensure that the questions they ask give them the answers they need - either blatantly, by having NPCs know the answer ("Why, yes, there is a new player in town") or by giving them answers that lead them to asking the right questions ("I don't know, but you might want to ask Mabel; She knows everybody").
Finally, if you run something in-between, where there's an expected plot, but players can deviate from it, there are no wrong questions. Sure, your players might miss this particular source of information, but that's just part of the game; Let them go off following whatever (false) leads they turn up; Plenty of time for them to realise their mistake and work out a new approach later.
...So, yeah, there are no wrong questions. The problem you really have is that you're shutting down attempts by players to investigate in ways you haven't thought of, without preparing alternatives. You can't blame your players for not reading your mind; If you allow them to fail, you need to provide some way for the game to continue when they do. (Alternatively, if the players hit a dead end, you could just declare the campaign over, but that'll probably lead to disappointment all 'round.)