Meet Kathy Kingston, guest blogger

Kathy is an award-winning consultant, speaker, professional fundraising auctioneer and author.  Her new book, A Higher Bid, How to Transform Special Event Fundraising with Strategic Benefit Auctions is launching later this week on May 20.  We thought you’d enjoy reading her thoughts about the Art of the Ask.

How to Master the Art of the Ask for Your Fundraising Auctions

At the age of 64, Diana Nyad became the first person on record to swim 51 hours nonstop from Cuba to Florida, in waters teeming with killer sharks and the deadly venomous Box jellyfish, without the protection of a shark cage. She’d tried five times before. When I watched the premiere of her new one-woman show, Onward, I was riveted. How could I help her use that courage to inspire others? I waited eagerly to write a check. Nobody asked.

This baffled me. Someone once told me, “Kathy, you’re more than a professional auctioneer. You’re a professional asker.” I’ll take the title! But in reality, I’m a “professional inviter.” Because inviting your supporters to make a difference for a cause that impassions THEM, is most important thing any of us does. This approach honors the person you’re asking, because it invites them to be part of a cause that’s meaningful and exciting to them. When they say yes to you, they feel great!

So why do we let so many chances slip away from us? Because we’re terrified to ask. We’ve gotten the wrong idea about what “asking” implies. We’re afraid it will feel uncomfortable and awkward and be taken as an imposition. And we’re just not sure the right way to go about it.  In this blog, I’ll show you how easy and rewarding asking can be. And how powerful.

Why We’re All So Scared to Ask

What’s the most commonly overlooked fundraising mistake?  Failing to ask. Failing to ask for people’s help, their time, their generosity, their stuff. There’s so much to ask for in a benefit auction—items, sponsorships, volunteers, donations, new guests, high bids, referrals, influence. I once counted and found at least 54 separate asks. So we’d better get good at it!

My goal in this blog is to drain the terror out of the ask. Because here’s the secret nobody tells you: People want to be asked. It’s flattering. It makes them part of the good work you’re doing. Sure, they might say they’re strapped for cash or way too busy at the moment. But even that can be an opening for you to further your relationship with them and find a different question, one they can say yes to. (More on that later.)

Right now, I just want you to realize that this kind of asking isn’t any harder than asking a passerby what time it is. In fact it’s easier, because you’re asking for such a good cause. And because there are so many ways to ask. Nonprofits have scrapbooks full of life-changing stories they forget to retell. They have urgent needs they never describe. Donors want—and need—to hear about the impact their gifts will have. They want to know they’re making a real difference. As long as you communicate that, your ask will be a powerful and welcome invitation.

Why Auction Volunteers, Staff, and Board Members Fail to Ask

1) They’re afraid they’ll be lousy at it, and they won’t ask correctly.

2) They’re terrified of rejection.

3) They’re afraid they’ll ask the wrong people, because they’re not sure whom to ask.

4) They don’t know how to follow up.

5) They don’t have enough information about the nonprofit they’re representing.

6) They have low self-esteem, and nobody ever reminded them that asking should be an out-of-body experience. They aren’t asking not for themselves. They’re asking for those who have no voice.

Yet People Want to Be Asked

A full 75 percent of Americans give to charities. Giving is up, and auctions have had record-breaking success across the country. I’ve just had the best five years in my 27-year history of being an auctioneer. In its last study, the National Auctioneers Association found that $16.3 billion were raised at fundraising auctions. And donor research (The Burk Donor Survey, 2013) indicates that 47 percent of American donors have more to give. Your auction guests, donors, sponsors, board members, and volunteers are just waiting to be asked.  And as you practice asking, your anxieties and fears about asking will fade, because you’re building relationships with people who are becoming genuinely interested in your organization and excited to open their hearts and their checkbooks.

How to Reframe Your Thinking

Asking isn’t an imposition. It’s an honor. You’re giving somebody the privilege of making a difference, and the chance to feel great about themselves for doing so. “No” isn’t rejection. Sometimes it means “not right now,” because the year’s philanthropic gifts have already been decided, or there’s no cash at present. My advice is, get as many no’s as possible, so you can get to the next yes. We know from professional advertisers that you need 11 impressions—11 asks—before someone takes action and says yes, no, or maybe.

Here’s The First Rule of Fundraising: People give to people. They don’t give to letters, texts or tweets, they give to other people, for causes they care about. So ask in person. If you can’t ask in person, have someone who knows that individual ask. Or do it by phone. Be prepared and be specific, and keep your donor at the center of your message. Listen closely, find out what aspect of your cause motivates that person, and do your best to connect them to that.  Open the conversation with your own personal involvement, and tell a short story—I’m talking 59 seconds, that short—about your organization. Then make sure the donor knows what you’re doing and why his or her involvement is critical.  And listen to what that donor tells you.

Who, When, Where, and How to Ask

Who? Simple. You ask the people who can say “Yes” without having to ask anybody else. The key decision-makers.  How do you find them? Ask the person who referred you, or research the organization online. Many companies have a community relations or a philanthropy page, and it’s pretty clear what the process is and who makes the decisions.


• Early in the fiscal year.
• Whenever you’ve just spent money with that prospective donor.
• Year-round.

Keep your auction packets and information everywhere—in your car, your gym bag, your briefcase, your house, your office—and keep templates of the forms on your organization’s website.  That way, when someone says, “Yes, I’d love to give you that Chef’s Dinner for four with wine pairing,” you can whip out the solicitation form and get it signed immediately.


Ask during a brief meeting or over coffee, but not over lunch. You could be on the verge of making your ask right when the waiter comes up and offers crème brûlée. You want to make sure there are no distractions. And you want to make sure you can hear—some places are very loud—so you can help connect that person’s needs to the work you do.


You have two basic goals:

• To connect donors to your cause
• To help them realize the impact of their gift

That means the first ask you make should be to yourself. Why are you involved with this organization? Why do you care? Have you made a contribution beyond volunteering? Consider this mindset: My nonprofit has tremendous value. We change lives. We keep families together. We better the lives of children. We save animals. We improve our community and much, much more. You can tailor that statement to your organization. You might even do it as an exercise with your auction committee or your board.  Ask your fellow auction committee members, “What if you woke up every day and said, ‘I can’t wait to see who I can tell our story of success to. I can’t to see who I can help’?”  Preparing for this means more about just thinking “Well, I’ve got to ask for something.” What you’ll be doing is connecting someone to something they love very much and helping them make a difference. When you come from that mindset, and you understand why you are involved, it makes the ask so much easier. Your passion and your generosity become contagious.

How Not to Ask—the Eight Big Mistakes

1) Not finding a connection or introduction. Asking is really about building a relationship with someone, so it’s important to find out what interests that person.

2) Not asking questions to find out what their true wishes and needs are.

3) Not asking for the gift at all, or not asking for a large enough gift.

4) Talking too much. Your job is mainly to listen.

5) Not waiting quietly after you make the ask. Don’t talk. Don’t apologize. Don’t cut it in half. Just wait, even if it’s five minutes. Sit there and smile. In fundraising they call that “holding the silence.” And it makes a difference.

6) Leaving it up to the donor to take the initiative. It’s your job to follow up, make the appointment, make the ask.

7) Not following up at all.

8) Not saying a sincere thank you in every instance—even when it’s just a thank you for the person’s time, because he or she has just said no to your ask.

How to Triage the “No’s”

It’s never easy hearing “no.” But what matters far more than that disappointing temporary answer is your response to it. If someone says no because there’s a problem with the organization, thank that person graciously and immediately report the problem to the person who can fix it. If someone says “Not this year,” ask, “Could I put you on the list for next year?” When people tell you, “I’m not going to have an opportunity to give you an item,” try another tack. Say, “Here’s a list of the items that raise the most money. Is there anything from these categories that you might have access to?” If you’re asking for a Fund-A-Need, lead, gift, or contribution and someone says no, ask for a gift at another level and talk about the importance of leveraging. And if someone says, “We just can’t help you at all” ask that person for his or her influence and referrals. Whom do they know that you could contact?  As a very wise person once said to me, “Remember, if you don’t ask, the answer is always the same.”  Just ask! And do not stop asking; be explicit about how much money you need and exactly why you need it and what a powerful impact your donor’s investment will have.

Ask unabashedly. Don’t stop asking. Be explicit. Help people understand exactly where and why you need the money. Most important, communicate how their investment will positively impact your cause. Tell them what a difference they’ll make. Forge a relationship that will endure. It all starts with a simple question.

So always ask.


Kathy KingstonInterested to learn more? Check out my new book entitled A Higher Bid: How to Transform Special Event Fundraising with Strategic Benefit Auctions. The book launches on May 20. As a thank you to those who purchase A Higher Bid on May 20, I’m offering over $600 of free gifts. To learn more, visit

Kathy Kingston, CAI, BAS is an award-winning consultant, speaker, and professional fundraising auctioneer and author. She has raised millions of dollars for non-profit and educational organizations across the US for nearly three decades. She is the author of A Higher Bid: How to Transform Special Event Fundraising with Strategic Benefit Auctions. Ms. Kingston created the Philanthropy Model of Benefit Auctions and founded the Fundraising Auction Academy where she teaches advanced fundraising, consulting and mentoring to nonprofit executives, educators, professional auctioneers, board members, volunteers and consultants. She holds a masters degree in education from Saint Louis University. Kingston Auction Company is the premier resource for record-breaking fundraising auctioneers, education and consulting. You can reach kathy at 603-926-1919 or

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