The fear of asking for a charitable contribution from a complete stranger (or worse, from a close friend) is legitimate. I certainly would not want to do that either. It puts everyone in an uncomfortable position. But if you follow the Benevon Model, by the time you ask a potential donor for money, they have been cultivated sufficiently to be ready to give. There should be no awkwardness or fear. It will merely be a matter of nudging them gently to do something they were already thinking about doing. If you are starting with someone brand new to your organization and you have followed the process as described, it should take no more than six to nine months before the person is ready to be asked.

Most of the fear associated with asking for money has nothing to do with money anyway. It is our fear of asking for anything. There you are at the fancy dinner party, sitting at the round table of ten people, desperately scheming how to have the salt or butter passed to you from the other side of the table. Asking seems like intruding. It seems rude. It seems selfish. From a very young age, we have been taught not to intrude. We call it fear of "please pass the salt."

When you overlay that fear of asking for anything with our cultural neurosis about money, it is no wonder we all have so much baggage about asking.

In our workshops, we remind our participants that people would rather say yes than no when asked for something. Think of the last time someone asked you for something and you said no. How did it make you feel? Most people feel like they are being mean when they say no. We feel like a much nicer person when we say yes.

So your job, as an asker, is to figure out what you can ask people for that they can naturally say yes to. We say that people can only contribute freely what they have in abundance. Anything else would be sacrificial giving, which is inconsistent with the principles of the new fundraising reality.

Make a mental list of a few things which you personally do not feel you have enough of right now. Perhaps you feel you don't have enough time or money. Now imagine that someone comes to you and asks you, very persuasively, to give them some of your time or money. Although you would like to say yes, if you are true to yourself, you would have to say no.

Now think of a few things that you have just about the right amount of—friends, family, clothes, pillows. If someone were to ask you to give them some of your friends or pillows for a project of interest to you, you would be more likely to say yes.

Finally, make your mental list of those things that you have in abundance. For women, shoes might be an example. For men, it might be sporting supplies or tools. If someone were to ask you to give some of those, it might feel as though they were doing you a favor to take them off your hands.

Your job with your donors and potential donors is to discover what it is that they have in abundance, and then to ask them only for that. You are no longer looking for sacrificial donations. You want to set it up in advance so that each donor can easily and naturally say yes to what you will be asking them for. Even if it means you may get less than you had hoped, you will have left your donors with a positive experience of giving, rather than that icky feeling. That way, they will be looking forward to staying in contact with your organization throughout the next year as you deepen your relationship further before asking them to give again.

In the Benevon Model, the key to successful, terror-free asking is the answer to only one question: Is this person ready to be asked? Another way of saying it is: "Have we gotten to know this person enough so that it would feel natural to ask them to make a financial contribution to the organization now? Would asking this person now be nothing more than nudging the inevitable?"

If your answer is anything other than a resounding "yes," if it feels to you as if it is too soon to ask, then wait. Go back, re-listen, re-involve, re-cultivate, until the person is sufficiently engaged.