When I meet with [my boss], I know that if what I am asking for requires money, unless I come armed with an idea of how to get that money, he does not listen. He generally gets defensive. So when other faculty or staff ask for advice on how to approach him, this is one of the things I tell them. Always come armed with a solution to the issue you are addressing. I think lots of folks come to him and say "we need to do such and such" and we need this much money. Since times are tough, it just puts more of a burden on him as a fundraiser. I find that if I solve the problem for him, there is a much better chance of him listening. This works with most folks by the way, who are responsible for paying for your idea. If you can also save them money, your suggestion just might be a shoe-in.
So, the moral of the story so to speak is know what you are getting into. Do your research and find out what they are thinking or how they react to proposals before you set up a meeting if you can. Even if you have no access, going in without a demand is a better strategy. If you start with I think I can help solve a problem, they might listen.
Owner/Artist & Professor, Nonprofit