The following is adapted from Harvey McKinnon’s book, The 11 Questions Every Donor Asks and the Answers All Donors Crave. For more information about the book, click here.

Have you ever wondered, “How do I get rid of this person?”

It could be a new co-worker who drones on about his Porsche and its 3.6L displacement. It could be the office gossip who keeps telling you who was caught after hours with whom. Or it could be the panhandler soliciting spare change, the telemarketer, or the door-to-door salesperson.

We often want to escape from an interaction. Do our potential donors ever feel the same way about us?

Maybe. But that doesn’t mean you’ll lose the gift. It does mean you’ll get less than you hoped for.

Decades ago when I made my first “ask” for an obscure little cause, I gathered quickly that the man I was sitting across from was less than enthusiastic to see me. I got the appointment because I could say that a prominent community member suggested I meet with him.

As I started into my well-rehearsed pitch, the man brusquely interrupted to ask his burning question:

 “Will you leave my office right now if I write a check for $1,000?” That was a decent gift for the time and for this particular cause. But it was considerably less than what I had in mind.

This fellow clearly wasn’t interested in the cause. And he had no reason to pander to me, a young unknown fundraiser. But I was in his office because I had invoked the name of a highly regarded personality: June Callwood.

I believe his real question to me centered around two things: “How much do you expect me to give?” and “How can I give as little as possible and still satisfy the ‘obligation’ to my friend?”

I admit I was taken aback by his abruptness. But I did manage a laugh and said, “Well, June Callwood said you might be able to give $5,000. Is that possible?”

I had read, no doubt like you have, that once you ask you must stop talking – immediately – and wait for the person to respond. So I simply smiled. In fact, I couldn’t stop smiling.

It seemed a good hour – I bet it was no more than 60 seconds – when he finally blinked and said, “Will you leave my office if I give you $2,000?”

I told him that would be very generous. Two minutes later I had a check in hand as I rode the elevator back to reality.

Be careful of what you ask for. You just might get it.

Another friend of mine, an accomplished fundraiser, was much luckier than I … or was she?

As the senior development officer of a large organization, she and the group’s president were approaching the head of a major corporation. They had a figure in mind. But they decided to be bold — and doubled the figure. If they were successful, the gift would be one of the largest ever to their organization.

When it came time to close the deal, the president of the nonprofit steeled himself and voiced the words, “We’d like you to consider a gift of….” He was sure his pounding heart was visible through his jacket.

He didn’t expect what he heard next – not by a long shot. “No problem,” said the CEO, “if that’s all you need, that’s great. I was willing to give a lot more.”

Oh my, how the solicitors wept inside. They did what all of us do from time to time: they asked for too little. In this case, seven figures too little.

Their first thought upon leaving with a check for the very amount they requested was: “We blew it.”

So while your donor will undoubtedly think seriously about the question: “How much do you hope I’ll give?” you have to think about it even more as this example illustrates.

You would like to say “Everything you have.” I advise against it. The real answer is an amount, determined in advance, that takes into account what you know about the potential donor and is based on the answers to these questions: “What is his relationship with the person or team asking?”, “How skilled, well-trained, and persuasive is the person asking?”, and “How clear and inspiring is your case?”

If you can accurately answer these questions, you’ll find an amount that’s within the prospect’s giving capacity but challenges her initial thoughts on what she thought was appropriate.

Is Charlie More Charming Than Me? Short Answer: Yes

My friend Charlie use to work for a technical institute, and at its open annual meeting he heard the magic words every fundraiser longs to hear:

 “I can’t believe what you’re doing here. I want to give.”

The words were spoken to Charlie by an older man whom he’d never met. “Because I didn’t know him, or what his capacity to give was, I suggested lunch a few days later. Meanwhile I discovered through research that he graduated from the school in the 1930’s.”

This gentleman, David was his name, had bailed hay for 13 cents a day to earn his tuition. The institute gave him a range of skills, and upon graduating he opened one profitable business after another. He was now very, very wealthy.

Over lunch, Charlie gave David and his wife an update on the school. Seeing that the couple was receptive, he said he’d develop a proposal for them.

At the follow up meeting a few weeks later, Charlie and the school’s president suggested a gift to build an automotive center (an area David was clearly interested in). “We asked for $1 million and offered to name the building after him,” Charlie says.

The older man paused, leaned across the table and, as though deciding upon a suit of clothes, said, “Do you have anything cheaper?” Something in the range of $100,000 to $300,000 was what he had in mind.

Sensing that David was struggling with the amount, Charlie suggested they reconnect at the end of the month. He did reiterate that the project they were offering was an ideal fit.

A few weeks later Charlie met over lunch with David and his wife. “He admitted the institute had changed his life,” says Charlie. “It gave him the foundation he needed. With tears in his eyes, David said he’d give us the million dollars.”

Charlie’s perceptiveness – he didn’t underestimate David’s ability to give – and his recognition that we all need time to make a decision of the heart, were amply rewarded.

The First Gift Often Leads the Way

“How much should I give?” is a question that continually runs through a donor’s mind.

Some, like June Callwood’s friend, want to give the least possible – but respectable – amount. They’ll plumb for that level.

But even generous people will refuse sometimes, for fear of embarrassing themselves.

Take my friend, Lucinda.

She regularly contributes $1,000 to causes she knows well. But her comfort level with unfamiliar groups is $100 to $250.

Should she offer this smaller amount and be viewed as Scrooge, or is it safer to say, “Not at this time”? Unless Lucinda’s is made to feel that her “initial gift” is a generous gesture, she does the latter – she begs off.

Too many organizations are insensitive to people like Lucinda. Sure, you want the big gift right off, but that rarely happens. Better to view the first gift as one of many, as an overture on which to build a lasting relationship.

Capital campaign expert Kent Dove once told me that a donor’s largest gift is often their 7th, 8th, or 9th gift. If there’s a more powerful reason to start the giving process, I don’t know it. And if doing so means welcoming $100 as you would $10,000, take comfort in the fact that philanthropists from Andrew Carnegie to Bill Gates have long used “test” gifts before committing much larger sums.

In addition to The 11 Questions Every Donor Asks, Harvey McKinnon is also the co-author of the international bestseller, The Power of Giving (Tarcher/Penguin), selected as an Amazon Best Book for 2005. His other works include, Hidden Gold, and the audio CD How Today’s Rich Give (Jossey-Bass), as well as the Tiny Essentials of Monthly Committed Giving (White Lion Press). McKinnon, who is one of North America’s leading fundraising experts, runs the Vancouver/Toronto based fundraising consultancy, Harvey McKinnon Associates (HMA) www.harveymckinnon.com.