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10 Questions To Ask Yourself Before Making a Big Ask

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Are you steeling yourself for the big Ask or hesitating and uncertain of your timing?

If you can answer each of these questions confidently, you should be ready to make that Ask. If you cannot answer each of these 10 questions, it’s likely that the donor is not ready to be asked.

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? Your executive director or development director? Would another board member enhance the asking team? To whom would this donor love to say yes?

3. Where will the Ask take place?

4. Exactly what will be asked for? Will it be for one thing in particular or a range of options?

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. What unexpected curve balls or surprises might the donor toss your way?

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? Asking for a memorial gift, a challenge or matching gift, a pledge to pay out the gift over several years, or offering a particular type of recognition?

10. What would be possible for your organization if the person says yes? Does the donor appreciate the impact their gift could make?

Don’t be discouraged if you cannot yet answer all 10 questions. It just means that you will need to cultivate your donors—by getting to know them individually and involving them in the parts of your work that most interest them. There will come a point in the process when you will be able to answer each of these questions.

Then, and only then, will you be ready to make the big Ask.

Did I miss any crucial questions? Let me know in the comments below!

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  • Beth keough

    I would also be sure you know how you will say thank you appropriately after they say yes, including recognition or naming rights.
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