Asking naturally—You can do this

Rule #1: The "ask" happens only after the donor has been educated and inspired about your work, has indicated an interest in becoming more involved, and has been cultivated personally before being asked for money.

The process of asking is fun and natural. The biggest challenge is to remember that it needs to be a dialog between two people who already know each other.

Before I go to ask someone for money, I always put myself in the donor's shoes. How would I like to be approached by one or two key people from the organization, knowing full well what they want from me? This is an organization I love and will feel excited to support. It feels as though I have guided myself through the cultivation process very naturally. I am wondering why no one has asked me to give until now. I have given many readiness signs to this group, hosted an event in my home, and invited friends to tour their offices. This is one of the two or three places I want to give my money. I love these people and support what they are up to.

To provide some encouragement for what may lie ahead as you enter the cultivation and asking process, let me share two heartwarming Ask stories from our alumni groups.

One executive director had planned to take a major donor to lunch with the board chair to ask the donor for a $1 million gift for their capital campaign. But on the day of the appointment, the donor had to cancel. Rather than postponing the meeting, the donor called that morning to apologize, insisting on knowing how much money the organization needed. Despite the executive director's attempts to hem and haw and reschedule the lunch so the Ask could take place in person, the donor persisted and the nervous executive director finally blurted out, "We were planning to ask you to give $1 million towards the capital campaign for our new building." The donor replied, "I'd be delighted to do that—just send me all the paperwork."

The moral of that story is to never underestimate the power of the highly personal donor cultivation work you will be doing. This same executive director, who has now raised over $10 million for this campaign, calls me often with amazing success stories and to ask me, "How can we attract and cultivate more of these wonderful donors who truly understand and appreciate our work?"

'Do it for Us, Bob!'
But let's suppose you aren't getting millions of dollars over the phone. Let's assume you'll need to go out and meet with people to ask. What else does it take to be successful when you ask?

We worked with one very shy executive director of a children's home who, even after many cultivation visits and practice "asks," could barely bring himself to make the Ask for $100,000. His 27-year tenure with the organization was a testament to his love of the children and the work of the organization. We suggested that when he goes out to make the Ask, rather than nervously anticipating all the ways things could go wrong, he should pause to recall his larger purpose. Imagine the little kids, tugging at your pant legs as you walk out of the office, saying, "Do it for us, Bob! You can do it! We need the things that money will buy."

He became a fearless, highly successful asker after that, and yes, he secured that $100,000 gift—for the kids!

Be Authentic
The key to a successful "ask" is you being a real human being—not a robot with a script, but a regular person who truly cares about this organization and this donor. The more authentic you can be, the better. Asking someone for money is an intimate occasion. It can be serious, playful, short and to-the-point, or long and drawn-out. No two Asks are ever the same, because no two people are the same.

I recommend you go into the Ask with an entirely different agenda: in those few minutes, see how related and connected you can become with the donor. It is all about listening for every cue and being much more focused on what they are saying right now than on what you should say next.

If they say yes and don't feel great about it, it's not a "win." You don't want to leave them with any sense of having been manipulated into giving more than they were comfortable giving. You don't need their contribution that badly.

You want each donor to feel as though they have sprinkled fairy dust on the most worthy organization in the world. You want each donor to feel so good about giving to you that they have no need for others to even know they did it. You want them to feel as if supporting your organization is a source of personal pleasure for them.

You have to let them know how excited you are to receive their gifts. You cannot be just a little bit appreciative. Let them know right away that their gifts are a big deal to you. Then you will have made a real friend. You have allowed them to truly contribute and feel the way you feel when you know you have made a real contribution.