While most fundraisers are comfortable asking for the major gift, few truly have a plan for how to move forward to ensure the gift will be realized. 

The reality is you must sell the idea twice—first to your donor and then to their advisor, because the larger the gift, the more likely it will be in a form other than cash, and part of it may be deferred.

How your donor answers some of the key questions below will help you form your strategy:

• What would your aspirational gift look like?
• Do you have a need for a charitable income tax deduction?
• Do you own any appreciated assets (stocks, real estate, paintings)?
• Do you own a business that you plan to sell in the near future?
• Do you have a traditional IRA or other retirement plans (deferred compensation)?
• Do you have a need for supplemental income?
• Do you have an updated estate plan?
• Are estate taxes a concern?
• Have you discussed this gift with your spouse and children?
• Who is the one person (e.g., an advisor) who needs to approve this gift? Can we schedule a call to discuss it with them?

Sharpe Group’s teaching philosophy has always been to help fundraisers gain confidence to ask some difficult—but important—questions. When your donor says, “I’d like to give, but …; you should be able to respond with “What if I could show you a way?” 

It may be as simple as a five-year pledge and a bequest or funding a charitable remainder trust with closely held securities for a business.

Making the ask is step one. To move forward, the next step is to gain the information necessary to show your donors how their gifts can have the greatest impact for your organization while fulfilling their objectives.