Fear of Asking? Trust your gut.

If you think you're the only one scared of asking for money, think again. Actually, think about the fear of asking for anything, even for the salt to be passed to you from across the table at a dinner banquet event. It's pretty amazing the gyrations we put ourselves through rather than ask for something so seemingly simple. Now compound that with our cultural insanity about money and there you have it: the recipe for disaster called asking for money or—more accurately stated—the fear of asking for money.

I tell behavioral healthcare executives to trust your gut when it comes to Asking. If it feels awkward and sales-y, hold off. Consider what more you'd need to know about this person before you would feel comfortable asking them for money. How much more bought into your mission would they need to be? What other questions should they be asking you? What more would you need to feel as though their gift to your organization were the start of a long-term relationship rather than a one-time transaction?

By the time you get around to asking someone for money, it should be nothing more than "nudging the inevitable." In other words, you will already have developed a true relationship between this potential donor and your organization's mission. That's right, you don't want the donor to be giving because of their connection to you or their friend on the board. They need to be giving because they understand and fully support your mission.

Here are some questions you should be able to answer about each donor before each Ask. And if you can't answer all of them, the donor is not yet ready to be asked. You will need to continue to cultivate this donor—by talking about and involving them in the parts of your work that most interest them—until they are sufficiently engaged.

1. Exactly who will you ask? Have you cultivated all the key decision-makers? Should spouses, partners, children, parents, or business partners be included?
    
2. Who will do the asking? Would another board member enhance the asking team? Who would this donor want to say yes to?
    
3. Where will the Ask take place?
    
4. Exactly what will be asked for?
    
5. What makes you think this person is ready to be asked now? Have there been any recent cues? Put yourself in the donor's shoes. Will they feel comfortable and receptive to an Ask now?
    
6. What are your biggest concerns, fears, and reasons for procrastinating in making this Ask? Often these are legitimate, especially if they concern donor readiness.
    
7. Does the person have an abundance of what you are asking for?
    
8. What is the person's self-interest in saying yes? How good would they feel saying yes? How sorry will they feel saying no?
    
9. What might strengthen this Ask? What could you add that would encourage this person to say yes? A memorial gift? A challenge or matching gift? More years to spread out the payment? A particular type of recognition?
    
10. What would be possible for your organization if the person says yes?

What more will it take for you to answer all the questions? What more will it take for you to establish a real relationship with this donor, the kind you might have with a board member or key volunteer? Is it time to schedule a lunch meeting or invite them in for a visit or tour? How can you connect or reconnect to deepen the dialog around the donor's key areas of interest?

Building real relationships with donors is no harder than building and maintaining a friendship. It takes intention, time and personal contacts.

Now, find someone to role play the Ask with you. Give them the background on the person to be asked. Tell them some of your biggest fears so they can be sure to play on them during the practice session. Then find another partner and practice again!