Back when I was a CDO I invited a generous community member to make a $100,000 gift for his local hospital. When he pushed back from his ravioli entrée and said “yes,” I expected a moment of cheerful celebration.

Instead, the donor immediately added these words: “But do not ever ask me to ask anyone else for a gift.”
His message made the moment awkward. I responded by saying that there must be a story behind his conviction about not asking friends.

He went on to tell me that a few years earlier a local organization he supported enlisted him as a campaign chairman to raise $100,000 for club improvements. They told him it would be an easy assignment: All he needed to do was pledge $10,000 himself and then invite nine of his friends to do the same.

He lost friends through the process. He described it as just awful to go to friends and have them turn their backs on him and later not want to speak to him.

I empathized, saying, “While we will never request that you ask for a gift, are you willing to suggest folks that we should be asking?” I added: “If so, would it be OK to have them know that you have given?”

The donor quickly said this approach would be no problem. “I am comfortable being on the team,” he said. “I just do not want to ever again ask my friends to make gifts.”

His unfortunate experience in the friends-asking-friends-for-money department isn’t necessarily the norm. Indeed, development professionals who have been in the business for a while know that such asks, when handled right, can be powerfully effective. Something was clearly amiss in the donor’s approach with his friends. Perhaps that particular campaign didn’t provide solid training and processes. We can only guess at what went wrong.

But we don’t have to guess about the broader truth of this donor’s experience. The truth is: Many people do not feel comfortable asking their friends for money.

And yet it is those very people – friends of your board members, campaign volunteers and engaged donors – who are some of your best potential prospects.

This can be a real dilemma.

Fortunately, the team approach based on Malcolm Gladwell’s best-selling book, The Tipping Point, is a good solution. It allows a more effective process in which friends simply introduce the opportunity for giving to their friends but are not be expected to close the gift by making the formal solicitation.

In this scenario, a board member, campaign volunteer, physician, executive – or simply an engaged donor – plays the role of Connector. This Connector introduces his or her friend to the staff development professional with whom the Connector is working. From this point forward, the Connector can be as much or as little engaged in the process and with the development team as is comfortable for him or her.