Podcast – Episode 31: How to Ask: Making Fundraising Magic Happen
In this episode of Auction Is Action with U in It!, Bobby D. Ehlert shares his keynote presentation from National Philanthropy Day in Las Vegas, delivered to a room full of nonprofit leaders, development professionals, and fundraisers from across the country.
This one is different from a typical episode. It is a live, interactive session packed with frameworks, real role-play, audience moments, and the kind of practical honesty that only comes from someone who has stood on stage and asked for generosity thousands of times.
If you have ever struggled with the ask, felt afraid of rejection, or wondered how to move a donor from maybe to yes, this episode is required listening.
Key Takeaways
One Question Stands Between You and a Million-Dollar Gift
The only thing separating your mission from transformational funding is the willingness to ask. Not the perfect script. Not the perfect moment. Just the ask.You Are Not Taking. You Are Giving.
Reframe the ask entirely. You are not taking donations. You are giving donors an opportunity to matter: to be a helper, a protector, a builder, an advocate. Fundraising is an invitation into meaning, not a request for money.The Three Elements of the Irresistible Ask: Clarity, Connection, and Confidence
Clarity means knowing exactly what you are asking for and why it matters now. Connection means understanding why this donor is in the conversation and what their tie to the mission is. Confidence means asking with a warm tone, a smile, and the certainty that what you are offering is worth saying yes to.The Four P Formula: Purpose, Picture, Proof, and Prompt
Purpose sets the agenda and answers why this conversation is happening. Picture paints what success looks like with and without the gift. Proof shows the evidence that your mission works. And the prompt is the actual ask: the clear, direct invitation for the donor to take action.Magic Fundraising Words That Work
"I invite you to consider making a gift that is inspirational to you." "Would you be willing to consider?" These phrases create an invitation without pressure. They give the donor room to say yes without feeling cornered.Hold the Silence for Eight Seconds
After you make the ask, stop talking. The first person to speak in a negotiation is the one who loses. Eight seconds of silence feels like an eternity but gives the donor the space to process and respond. Practice it. Get comfortable with it. The pause is where the yes lives.No Does Not Mean Never
No often means not right now. Ask when would be a good time to follow up. Ask how else they might want to be involved. Explore time, talent, and team before closing the conversation. Every no is a continuation of the relationship, not the end of it.Storytelling Is Spellcasting
Facts are arbitrary. Stories are universal. A 30-second story about one person whose life was changed by your mission will do more than any data point. Sell the sizzle. Create the emotion. Make the donor feel the impact before you ask them to fund it.Donor-Centric Language Centers the Donor as the Hero
Viewers like you make this possible. Your gift helped us do this. You are the reason this happened. The donor is not the audience for your mission. They are the hero of the story. Your job is to be Yoda, not Luke Skywalker.More Yeses Create More Yeses
Generosity compounds. Every yes a donor gives, whether it is attending an event, making a small gift, or joining a committee, builds trust and deepens the relationship. The ripple effect of one yes can eventually lead to the transformational gift that changes everything.Quality Over Quantity in the Room and in Your Pipeline
Events are shrinking but revenue is growing for organizations that focus on the right donors. Two hundred people with connection and capacity will outperform five hundred who are just filling seats. The same principle applies to every ask you make.Practice Is the Path
Great askers are not born. They are built through repetition, discomfort, and daily practice. Negotiate at Starbucks. Ask your kids with eye contact and a pause. Practice the ask everywhere so that when the moment matters, you are ready.
FULL TRANSCRIPT
Bobby D.: Okay. All right. Well, what we're going to do is we're going to do what we call a family photo because this is a momentous occasion. Second annual, the most ever, tripled the number. And everybody sees the world's largest business card in front of them, right? Okay, everybody grab your world's largest business card, also known as a bid paddle. I'm sure many of you know what to do with these. We're going to take our family photo. Everybody take those paddles and hold them way up. Hold them up. Look at that. All right. We're going to see how well you follow instructions. Everybody, put them down. Put them back up. Put them down. Put them back up. To the left, to the right. Wave them around like you just don't care. Get those wiggles out this morning. Look at that. There we go.
You can't have an auctioneer on stage without expecting an auction, right? We're going to do a mock auction. This is just fun. I've got my associate, my left-hand man, the one and only Dusty Clink. Say hi to Dusty. Dusty will be back at the table all day today. What we are going to auction off right here this morning is the most important ingredient of a fundraiser's day: a cup of coffee.
Here we go. Who wants to go for a dollar? I get a dollar. $2. Three. Five. 10. 20. 30. 50. $100 for a cup of coffee. 200. 300. $1,000. 2,000. 5,000. 10,000. 20,000. 100,000. A million right there. Everybody, you all know my favorite four-letter word. It starts with S. S-O-L-D. Everybody on the count of three for a million dollars. We're going once, we're going twice. One, two, three.
You got it. Here's your cup of coffee. Free refills included.
So we're going to get started with our presentation here today. We're going to be talking about how to ask. Show hands. Who loves to ask?
I love professional fundraisers who are willing to ask the hard questions. I want to ask you something. What is standing between you, your mission, and a million dollars? Just one question. That's all it is. One question away from that next transformational gift. From the gift that could transform your organization and transform so many lives. The power is in your hands and within your heart. And we're going to be unlocking confidence, connection, and clarity with every ask. Because I am an asker. Every day that I am on stage, I am asking people to do things that stretch them.
I want to invite everyone to stretch a little bit today and be in that uncomfortable zone, because that's where growth happens. Think about going to the gym. You're working those muscles. You're on the treadmill, you're lifting weights. It's that soreness, that discomfort, that changes everything.
My name is Bobby D. Over a billion dollars raised. Hundreds of clients nationwide. We have a wonderful team of auctioneers all across the nation. We can serve nonprofits anywhere, anytime, for any reason, with any budget. And the most important number is 100% engagement. I want to see a show of hands: who has ever had 100% engagement at their event where everybody made a donation? It is absolutely possible. I've actually seen 110% participation, where some people gave more than once.
Today is going to be a little interactive. We're going to adjust our mindset from fear to flow. Why is asking hard? Who has a hard time with asking? What is the hardest part?
They say no. Yes. No is one of two answers you're going to get. What else? I don't want to overuse the pool. Asking too much of the same donor base. Very common. Embarrassed. Yes. Especially when asking for a major sponsorship or a major gift. You don't want to look silly. You don't want egg on your face.
Asking is hard. It's an uncomfortable topic. Fear of rejection. What if they say no? Here's the reframe: you are not taking anything from anyone. You are not taking donations. You are giving an opportunity to the donor to give them a chance to matter, to make something amazing happen in the world. We are only one question away from the next million-dollar gift. And the magic phrase is: we are not asking for money. We are asking for meaning. We are creating an invitation.
If you can think of it that way, that you are just providing an invitation for whoever wants to be a part of your nonprofit, whether as a volunteer, a donor, or a sponsor, that changes everything. The psychology of generosity is that people want to be a part of something bigger than themselves.
Now let me share some of the truth about fundraising. A fundraiser's job isn't about asking for money. It's about asking for connection. As a fundraiser, it's not your job to make people care. Your job is to create opportunities for connection and attract individuals who have alignment with your mission, with your cause, and with the impact you want to create in the world.
And I want everyone to create an abundant mindset. Who's scared that grant funding is going away? Yes. It's scary. We are in unprecedented times and many organizations are asking what they do if major funding disappears. But here's the good news: there is more than enough money out there to fund every mission ten times over. The only thing holding us back is the willingness to ask. There are corporations with millions of dollars they want to give to you. There are family foundations that want to fund missions like yours. There are major donors who want to continue to give. And there is an entire new generation receiving the great wealth transfer happening right now. All you have to do is ask. It's not about the money. It's about the meaning. What does this fundraising fuel do? What does it make possible?
People don't give to causes. They give to connections. Yes, your cause is worthy. But it's the connection between your cause and a donor who wants to make a difference in the world that unlocks generosity. We are here to create opportunities to attract abundance and to be magnetic for it.
Here are some magic fundraising words. Friends, I want to invite you to give. I want to invite you to be a part of something bigger than ourselves. I want everyone to be a part of this collective giving moment. I invite you to consider making a gift that is inspirational to you. That is not a direct ask. That is an invitation. And with that invitation, I'm asking you to consider: would you be willing to consider making a gift? Not would you make a gift. Would you be willing to consider? These words and phrases used in your ask conversations will get you far more yeses.
Now, the three elements of the irresistible ask: clarity, connection, and confidence.
Clarity means knowing exactly what you are asking for. What is it? A donation? A sponsorship? A multi-year gift? Dollars toward a new facility? Be specific and tangible in your ask. When the ask gets muddy, donors disengage.
Connection means understanding why this donor is even in the conversation. Why are you having coffee with them? Why are you calling? What is their connection? Start by asking: why is this work important to you within your philanthropic story? What is it that we do that you love? When they tell you, you are able to connect their desire to your mission. Because you want this to happen, and this is what we do. And we want to invite you to consider making a donation so that we can continue to fund our programs.
Now, donor-centric fundraising. Does anybody know Penelope Burke? Her book on donor-centric fundraising changed the way many of us think about this. The easiest example of donor-centric language is something we all grew up hearing at the end of PBS: viewers like you make this possible. Donors like you make this possible. Your gift helps us with this. You are able to make a beautiful transformation within our organization. The donor is always at the center.
And then there is tone, timing, and the story transformation. Here's the difference between two versions of the same ask.
Version one: Hello, Mr. and Mrs. Smith. Thank you for sitting down with me. We've got this really great mission and we're doing all this really great work, and, um, I don't know, I wanted to see if maybe you might want to donate $10,000. Maybe. If you don't, it's okay. I know it's a lot of money.
Version two: Hello, Mr. and Mrs. Smith. Thank you so much for meeting with me today. I'm so excited to learn about your desire to help our mission, which impacts kids in this way. I know that through your previous donations, you've helped us create this level of impact. And we have a big opportunity for you. We want to create this program, and we know with your connection that you want to be a part of this. I want to invite you to consider making a donation of $250,000 so that we can make an impact in the world.
Who's going to say yes to version two?
And yes, it feels scary to ask for big numbers. But zeros are only a mindset. There are individuals for whom a six-figure gift is nothing. There are others for whom a three-figure gift is everything. It is not our place to judge when too much is too much. It is our place to create the opportunity, extend the invitation, and let the donor decide what is inspirational for them.
I always say from stage: friends, I don't want you to give until it hurts. I want you to give until it feels good.
Now, the four P formula of the perfect ask. Purpose, picture, proof, and prompt.
Purpose: what is the purpose of this gift? Why are you having this conversation? Set the agenda. You can even foreshadow it by saying, at the end of our conversation, I'm definitely going to ask you for something. That sets the expectation early and removes the surprise.
Picture: paint two pictures. What does success look like with the gift? And what does the situation look like without it? We are in a time when people are hungry for hope. Give them something to lean toward.
Proof: show the evidence that your mission works. Share the result of what past fundraising has made possible. This is the result of the hero's journey. Emma came to us at age three with a cancer diagnosis. Her family spent the next year in and out of hospitals. But because of donors like you, Emma had access to cutting-edge care, family housing, and the emotional support her family needed. Today, Emma just celebrated her second birthday cancer-free.
That is storytelling. That is spellcasting. Find your Emma. Find your Eli. Build a 30-second story you can pull out in any conversation that makes the mission real and personal. Facts are arbitrary. Stories are universal.
Prompt: this is the actual call to action. The ask. Think of it like a prompt to an AI tool. You have to tell it what to do. You are just prompting the donor to take an action, whether that is becoming a sponsor, attending an event, making a gift, joining the board, or volunteering. Because we all know that 70% of volunteers end up becoming donors.
Now, handling the silence.
How did that silence feel? That was eight seconds. People can't even ride a bull for that long. After you make the ask, hold the space for eight seconds. Very simple: would you be willing to consider making a donation so that we can do this? And then you wait.
In that eight seconds, one of two things will happen. Either the donor fills it by negotiating or softening their own position, or they say yes or not right now. Either way, you win by staying quiet. The first person who speaks in a negotiation is the one who loses. Hold the space. Smile. Breathe. And let the pause do its work.
Do not rush the response. And practice this everywhere. At Starbucks. At Macy's. With your kids. Ask for things in everyday life with a smile and a pause and get comfortable with the silence. The more you practice, the more natural it becomes.
And when you get a no, do not take it as final. Ask when would be a good time to follow up. Ask whether there are other ways they might want to be involved. Explore the four T's: time, talent, treasure, and team. Maybe this person is not ready to write a check but they know three people who are. Maybe they want to volunteer first. Maybe they can bring their network to your event. No often means not yet. And sometimes the entire relationship that leads to a major gift starts with a single $500 donation to a champagne paddle drop.
I was working with the Leukemia and Lymphoma Society on Long Island. There was a very wealthy individual in finance they had been trying to reach for years. He came to every gala but never bid, never participated. Nothing. At the end of one paddle raise, we created a collective giving moment with a bottle of champagne as the final prize. This gentleman wanted it badly. He donated $500 and won. The organization now had access to him. They could thank him. Show him the impact. Build the relationship. The following year he came in as a $10,000 table sponsor. The year after that he became the title sponsor and provided a $250,000 match in the paddle raise. It all started with $500 and a bottle of champagne.
Sometimes the entry-level donation is all you need to start the conversation.
Now let's talk about the ripple effect. Every yes creates more yeses. The donor journey starts with yes. Yes, I'll attend. Yes, I'll sponsor. Yes, I'll make a gift. And each yes builds trust, deepens the relationship, and opens the door to the next ask. The butterfly effect is real. That first yes can ripple out across networks, across years, across generations of giving.
And here's a reality check on the current fundraising landscape. Events are shrinking. Organizations are not selling as many tables or seats. But more bodies does not mean more bucks. Quality over quantity. I have been at events with 200 people in the room that raised $320,000. And events with 500 people that barely raised $75,000. The difference is who is in the room and the relationships that have been built before anyone sits down.
For new fundraisers: start now. Start today. Build a culture of asking in your organization. Ask your team for help. Ask for more responsibility. Ask for a raise. Practice the ask everywhere. Because this is not the job of fundraising. This is the art of fundraising. And like any art, it takes practice, patience, and the willingness to be uncomfortable until it becomes natural.
Magic lives in clarity, connection, and confidence. Every ask is an opportunity to change the world. And when you ask with heart, the world answers with generosity.
My name is Bobby D with Call to Auction. Thank you all so much for being here today. Go out and make fundraising magic happen. Get your yeses. Make your asks. Put yourself in that uncomfortable place. You are offering meaning, not money. And you are all world changers. You've got this.
Ready to Raise More?
At Call to Auction, we specialize in turning galas and fundraising events into mission-driven, revenue-generating experiences. From paddle raises to live auctions, our team knows how to excite donors, engage audiences, and inspire generosity in the moment.