When I meet with someone to go over requirements my goal is to really understand what they want.
The first rule I have is to not worrying about looking stupid or asking stupid questions. It is the person or group you are meeting with responsibility to convey their requirements to you in a way that you understand. Asking questions shows that you are serious about understanding what they want.
I like to use a basic cycle of: Listen to their question, repeat their question and then express what you do not understand about the question.
For example,
Q: "Adam, we are needing a dynamic system that will notify our users to changes made to it".
A: "Ok - so you want a dynamic system that will notify your users to change made to it. So, what exactly do you mean by "Dynamic?"
and so on....
Don't be afraid to say "I really don't understand what you are wanting. This is what I understand so far, please help me fill in the blanks...
Derek