“The true spirit of conversation consists more in bringing out the cleverness of others than in showing a great deal of it yourself; he who goes away pleased with himself and his own wit is also greatly pleased with you.” -- Jean de La Bruyère, “Of Society and Conversation”, The Characters of Jean de La Bruyère
1. First of all, it's OK if you don't want to ask someone for a gift. Really. Don't make yourself, because you'll come across as disingenuous and the donor will be uncomfortable. Many asks are not made 1-on-1 -- either go with a colleague who IS comfortable, or find someone else to do it.
2. Do your homework! Never go into an ask (or a cultivation meeting for that matter) without knowing as much as possible about the askee. Like Columbo, ask questions that you already know the answer to, such as what other organizations they support.
3. Make sure you personally believe in what you're asking for. Have colorful, inspirational and real stories. If you're taking someone with you, that person should have already given to your organization.
4. Rehearse beforehand, like an actor going on an audition. The worst the person can say is no, and that's not so bad. And if they do say no, they might say yes next year. Life goes on.
5. I rarely do an ask over a meal, but that's a personal preference from many years of asking. Why? Because when dessert is served and you haven't asked yet, everyone gets palpably nervous. Put yourself in the donor's place.
6. If you do go out to a restaurant for the ask, make it a nice one -- but not too nice.
7. Always let the donor know in advance that this meeting is going to be about asking them for a gift. No one like surprises.
8. Don't give the prospective donor too many choices. You won't need to if you've done your homework correctly.
If you ever want to talk over an ask strategy, give me a call!