"Ten Questions You Must Be Able to Answer Before You Ask for a Gift" by Terry Axelrod

You should be able to answer all of the following pre-Ask questions about each donor. And if you can't, that's a sign that the donor is not 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?
    
    

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!