Ask more questions
The best project managers, designers, business leaders, account managers, and entrepreneurs ask a lot of questions.
That’s how they find out what someone really means, wants or thinks.
This might sound blindingly obvious, yet every single day I spot instances where someone should have asked more questions. Lots more questions.
For example, if the users of your web app say they want image upload image to be easier, what precisely do they mean? Maybe they want your app to have an image upload feature on every single page, or maybe they just want the one you already have to be less complex. Or allow larger file sizes?
Ask more questions before you act on any input.
If you’re in the web dev business make sure you know what clients are actually after when they say “I want it to look like a ‘web 2.0′ site” (as horrid a statement as that is, it still means something to the client). Do they mean larger font sizes to improve legibility? Or do they just mean gradients galore? Or did they happen to look at the Mollom site earlier that day, labeled it “web 2.0″, and now want theirs to look equally welcoming?
Ask more questions. The more you ask the more you’ll know, which in turn leads to less uncertainty and frustration, which makes you happier, your output better and the user or client more satisfied.

Johan H
July 28
I agree, it’s all about trying to drill it down to the actual requirements, and to make sure your and the customer’s vision is the the same.
If they leave you with these open-ended questions you talk about it’s fairly natural that you end up asking lots of questions, since you get triggered automatically by the vagueness of their request, and you’ll eventually get down to something that is workable - using your skill as a professional in the process.
The tricky part can sometimes be when the solution decision process happens before you’re involved, and the customer decides themselves and asks something really straightforward of you, not really triggering the necessary questions.
You end up implementing things, without a clear vision of where the result is heading, which will lead to problems in the end.
So once again, ask more questions, especially the all important one “What do they REALLY want?” - cause the odds are you’re better at guiding the customer than they are guiding themselves.