How to tell if giving someone money is the right thing to do

Suppose your child, or friend, or a stranger on the street asks you for some money.  What do you do?  What do you ask yourself?  How do you justify either giving them money, or denying their request?

Some of the questions that swirl through my head are: "Why did they let themselves get into this position?", or "Why does this person always need help?".  I'm fixated on the person and their need and how if they took better care of themselves, then they wouldn't be bothering me right now.

I find myself giving the bum a $1 because I think he needs it, and I give it grudgingly because I think he shouldn't need it.  Surely this is a warped way to view an experience of giving and receiving.

So, I've decided that there is a better way to think in this situation.  I will change my focus from the requester's need, to the requester's ambition.  If the beggar has any ambition, I simply ask myself: "is the ambition good, and will this gift help enable that ambition?"

Of course, there are those folks who just don't seem to have any ambition at all.  Perhaps the question for that is, "Which action will stir up the most ambition in this person, giving money, or withholding it?"