Yes, if you mean you have done several readings with the same question for 'clarification' then I say there's your problem. You should only ask once IMO and if you can't see the answers you wanted, consider the possibility that you could be missing the message. If, on the other hand, you are changing the question each time, it could be that you are in fact asking questions that are too similar, exhausting the subject, your subconscious mind can grow weary of being pressed about the same issues, particularly if it knows it has answered already and you didn't hear. I think of it like pestering: nobody likes it do they?
Have you considered, in situations where a lot of information is needed, doing a much more in-depth reading to begin with, and making that your main focus? you could try putting more effort into the preparation and choosing the cards, or make the operation into several stages to ascertain different levels of the issue...you know: have a special bath, light candles and incense, invoke/ petition whichever otherworldly beings you think appropriate, make sure of having some peace and quiet, that sort of thing, of course all in proportion with the importance of the reading.. Make sure to write down the whole spread in your notebook along with any feelings/ intuition/ other significant factors so that you can look at it with fresh eyes later if necessary, rather than a repeat reading which, in my experience, is never a good move.
One more thing (promise!), if you have come up against a brick wall already, then I think you need to leave it a couple of days before asking again, unless it's a real emergency.
Zoe