Successful philanthropy is rightly focused on the needs and goals of the donor. When you put yourself firmly in the shoes of the potential major donor—and really understand what they desire, you are on your way to success—not the quick kind, necessarily, but the most important kind, which is deep and long-term.

The balance of course is that you have a mission and a vision to accomplish. And you need increasingly more resources to move forward. You want to be traveling on the road to where your donor’s goals and your mission intersect, and then align.

Here are five things to keep in mind:

Listen, really listen. The first few stages of cultivation should include you asking many questions about their interests and then listening between the sentences. At one meeting in a nice, but certainly not ostentatious home, I noticed a pencil sketch sitting over the mantle. I was curious as to why it was so well-lit and such a focal point of the room. When I asked to see it, I noticed the signature – some guy named Picasso. That gave me obvious insight into the prospective donor’s interests and tastes.
Engage in conversation and, to the extent that the donor is interested, meaningful involvement with your cause. That can mean different things to different people. The profile of a donor isn’t necessarily that of a volunteer, but meaningful involvement is needed. That could be something hands on at your food pantry or it could be involvement in expressing their preferences in the design of a building. It could be getting their views on your white paper for your newly-proposed program. When they begin writing in the margins of that paper, you’ve got a real conversation and an emerging partnership.
Align their chief interests with that of your organization. Years ago when a builder sold his interest in one of his unrelated businesses, his philanthropic interests went back to his true love and he wanted to build something on a school campus. What school doesn’t have that need? Such an interest allowed the school to develop and then accelerate its vision to become a leader in the sciences because that aligned with the builder’s interests.
Solidify. As the conversation progresses, the prospective donor can become so engaged that they guide you not only toward their specific interests, but even to the amount you should ask them for. Part of the art of fund raising then becomes understanding that the amount may be a starting point for a discussion rather than a cap.
Ask. Yes, absolutely ask for the gift, but do so in a timing that makes “yes” a forgone conclusion. If you’re on pins and needles when it comes time to make the request, you probably haven’t spent enough time listening, engaging, aligning and solidifying.

Ideal philanthropy is truly a win-win in every sense of the term. Prospective major donors have always been smarter than me anyway and their philanthropic intent is already there. If you can’t create a match within your own organization, it’s much more faithful to steer the donor to one who can help them. The goodwill always comes back to you and so will the contributions.