People are afraid to ask for money. Even if they are the most successful venture capitalist or a hedge fund manager, or even if they ask for money all day every day, many successful individuals demure when asked to request $100 for an annual fund. Money does not magically appear. Interested parties need to ask whether they're comfortable with asking or not.
Many people appear to be unaware that there is a time-tested process for raising money for your school. Only in the last 40 or 50 years has fundraising been formalized as a permanent component of running a school. Up until the 1960s and 1970s fundraising was generally not seen as an iterative process. We can now safely say that most approaches have been tried and we now know what works and what does not work.
Boards do two things: they hire and fire the head of school and they secure the financial resources for the institution. If the board does not understand that responsibility, as a group and as individuals, then no amount of fundraising in the world is going to help you secure resources and make good decisions regarding them.
Every single parent in your school supports a cause and the competition for these dollars is fierce. Donors are solicited for United Way and the American Red Cross, and relief efforts for a disaster overseas and countless other charities and non-profits. There are limitless worthy causes and the decisions that donors need to make are more and more complex. The philanthropic marketplace is becoming as crowded and as competitive as the market for cars, for computers or for any other product or service. There is competition for donor's dollars from both within the school and outside of it.
Even 10 years ago books were published that said, “if you want to reach out to a donor first you have to send them a handwritten letter. Then you follow up with a phone call and then you have a meeting.” Nowadays every person you’ll want to talk to has a cell phone, a home phone, a work phone, an email address, a work email address, and an answering machine that nobody listens to. These technologies can come to represent so many rocks that donors can hide behind. The logistics of making contact with a potential donor has become increasingly complicated.