The Paradox of Asking

Philanthropy — and the hallmark of successful advancement programs — always exhibits just the right "personal touch," which is enabled by personal relationships. But what happens when relationships appear to close doors instead of opening them?

Here's what I mean. We've heard it from volunteers, and even from other advancement professionals: "I'm too friendly with her to ask her for a contribution." It is well-known that most people feel uncomfortable asking a friend for a gift.

The paradox here is obvious. As development professionals, we try to leverage pre-existing relationships between others to set the stage for an optimal gift ask and close. Typically, the stronger the relationship, the tighter the connection is between the "asker" and the prospect, the greater the chance for a successful outcome. And yet, volunteers are very hesitant 
to have these conversations with their friends and colleagues.

So what is an advancement officer to do? I have demonstrated this paradox to leadership volunteers during many board trainings I have conducted. The exercise goes like this. Volunteers are asked to rate their feelings in different fundraising situations using an entertaining scale of emotion icons. They are first questioned about their comfort in asking for a gift. Inevitably, most volunteers feel more comfortable asking a relative stranger for a gift than someone they know well. Then volunteers are asked to rate their feelings about being asked for a gift themselves. Most rate having the greatest comfort when being asked by a close friend.

Go figure. You can imagine the tone in the room when this revelation is revealed. There is laughter and a few "wows."

So how do we resolve this paradox to the benefit of our advancement work? The path to success is often revealed once the 800-pound gorilla in the room is disarmed. Encourage your volunteers to express to their friends their discomfort with the situation. It is the sincerest of gestures to admit a weakness or discomfort to someone else. Most people feel a huge sense of relief once this is expressed and out on the table.