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How to Overcome Infatuation and Make the Hard Sell

What do you do when love — okay, infatuation — is blinding you and keeping you from making the hard sell?

How to Overcome Infatuation and Make the Hard Sell

I think I might be in love with Mr. Perfect. He is my Kevin (the stable oldest Jonas brother), Joe (the sexy middle Jonas), and Nick (the passionate, cause-y Jonas), wrapped into one perfect grown-up with modern glasses. When I meet with him, I feel like a silly 12-year-old girl. Oh, and he's rich.

My husband knows and thinks this is all very funny. Here's the real complication: I should be asking Mr. Perfect for money. He believes in good causes and good organizational management — and Do Something's mission and business model are right up his alley. But I just can't do it. We've had lunch, and we've had coffee, and it was dreamy. I think at one point I actually sighed out loud, in awe.

Everyone who raises money will tell you to prepare your basic pitch: Know your own case. Understand the motivations of the target. Answer questions directly. Look the target in the eye. But why doesn't anyone ever talk about mastering your emotions? Turns out fund-raising — and sales of most kinds, really — is actually a lot like courtship.

Asking for money has always been second nature to me. Whether it was selling Girl Scout cookies or working as a supermarket clerk, the exchange of money (that is, taking someone else's) was easy. Charity fund-raising is just another version of that exchange. The donor gets value from giving, whether it's Thin Mints for helping scouts or satisfaction for donating to Dress for Success and helping women reclaim their destinies. And then I sit down with Mr. Perfect, and I don't even know how to spell "value" anymore.

Many fund-raisers (and entrepreneurs) fall into versions of this trap: They're so passionate about a project that they can't speak in normal human tones. Remember being a teenager and, OMG, so in love that your hands sweat and your mouth goes dry? It can be like that, whether you're enraptured by Mr. Perfect or the Perfect Cause.

So how do you overcome that infatuation when you're making the ask? I turned to the experts for advice.

First, I called Peter Wilderotter, who heads the Christopher and Dana Reeve Foundation. He has been in the not-for-profit sector for decades, raising millions for things he cares about, (sometimes) from people he genuinely likes. He suggested that I stop meeting in social settings. Stick to the office. Steer clear of personal conversation. Keep the meeting short. Never forget that your target cares less about the cause than you do; your job is to convert him. "It's not enough to have the angels on your side," Wilderotter says. "You need to make the angels work for you."

Then I phoned McAlinden Associates, a firm that coaches executives to communicate effectively. They told me to prepare more deliberately before meeting with Mr. Perfect. What are the three things I want to impart? (There's no better way to squelch the frisson than to think about what I want to impart.) "Make explicit the links between the key messages in your one-minute pitch and the issues that matter to him right now," EVP Douglas McAlinden said. "Your pitch then becomes a discussion of how an investment would help him solve a problem he cares about."

For demographic diversity, I asked a 15-year-old boy with an excellent dating streak. J.P. Steers suggested that I "talk to him on Facebook or AIM, like make fun of him for something."

Finally, I asked my nanny, who, given what we pay her, is clearly gifted at requesting money. She confessed that she always asks me at the end of the day, when I'm tired and looking my worst. Smart woman.

Nancy Lublin founded Dress for Success and is CEO of Do Something. Email her to guess who her Mr. Perfect is — he has a rich and famous dad — or to tell her about yours.

A version of this article appeared in the June 2009 issue of Fast Company magazine.

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