Are you working with a board, committee or task force that is raising money for an initiative or for your organization? Are these volunteers sometimes hesitant to actually make the ask of prospective donors?
If so, remind them of this: They are not asking for money for themselves. They are asking for money for the beneficiaries of the mission of your organization, whomever that might be -- the poor, the unemployed, youth, senior citizens, students, the handicapped, the sick. Can you see the difference? When you focus on mission-driven fundraising, your volunteers can step out of their own skin and speak on behalf of the beneficiaries and help the prospective donors connect their interests to that mission.
When working with a committee raising money for an organization that helps children affected by child abuse, the co-chair of the committee (a volunteer I would like to clone, by the way) kept reminding her volunteers to "remember the children; you are asking for the kids." It was her mantra for each meeting, each e-mail, each phone call, and it worked! The committee exceeded the $100,000 goal ahead of schedule.
The children will benefit.