211 | How Women Can ASK for More and Get It with Dia Bondi

Dia Bondi - Love, your Money



Welcome to episode 211 of Love, your Money! In this episode, I’m interviewing the amazing and eccentric Dia Bondi.


If you know my 7 Steps to Wealth framework, you know that Step 3 is ASK. You can’t really boost your financial game without making offers and asking for more; ask for a raise, ask for the sale, ask someone to work for you, ask for a promotion…You catch my drift. It’s a fundamental life skill, and if you lack it, your progress is bound to stall. If you unabashedly ask, you might hear more “NOs” than if you never asked, but you’re also more likely to experience rapid growth and achieve your goals much quicker.


Today’s guest, Dia Bondi, fully embraced this concept and took it to a whole new level when she wrote her new book, Ask Like an Auctioneer: How to Ask For More and Get It.


In this episode, Dia and I talked about her time attending auctioneer school, where she learned to approach rejection differently. She then turned that simple but profound idea into a workshop, a TEDx talk, a movement, and now a book. So buckle up, this one is juicy!

Here’s what you’ll find out in this week’s episode of Love, your Money:

  • Asking for more in your career as a woman
  • How Dia became an auctioneer
  • Why you want to hear “no” in negotiations
  • Using psychology to make more money
  • Detaching your worth from what you’re paid
  • Why defining a purpose can aid your negotiations
  • Turning ideas into books, courses, and workshops
  • The value of having a bias for action

More About Dia Bondi

Dia Bondi is the CEO and founder of Dia Bondi Communications, which helps high-performance professionals speak with power and purpose at crucial communications moments to amplify their impact and reach their goals faster.


Dia is the secret weapon behind some of the world’s most influential leaders and VC-backed founders. Dia has led workshops at corporations including Quartz, Twitter, and Meta. She helped Rio de Janeiro secure the 2016 Summer Olympics and was the communications coach for world leaders at UN gatherings.


Following a curiosity, Dia attended auctioneering school and has since translated the techniques she learned into a program that prepares women to ask for more and leave nothing on the table called “Ask Like an Auctioneer,” which catalyzed her mission to put more money and decision-making power in the hands of women so we can change everything for all of us.

Inspiring Quotes

“Price is the measure of value, not a way to define your worth or worthiness.”

“What dictates how much courage we can muster is usually what we think we can get a YES to.”

“Stop deciding what other people are going to say yes or no to. Let them decide.”

Enjoy the Show?​

Hilary Hendershott: Alright, let’s get to it. Today, I’m interviewing the amazing and eccentric Dia Bondi. If you know my Seven Steps To Wealth Framework, you know that step three is ask. You simply cannot grow your financial life unless you make offers and ask for more, ask for a raise, ask for the sale, ask someone to work for you, ask for a promotion, ask someone to prepare your tax return. You get what I’m saying. It’s a critical life skill and if you don’t have it, your results will languish. If you ask unabashedly, you will hear no more than you will if you don’t ask but you’ll also probably achieve hockey stick growth and achieve your goals much faster. Dia took that whole idea and ran with it. Dia authored a book called Ask Like an Auctioneer, which is out in November of 2023. In this interview, Dia and I talked about the aha moment that for her came out of attending auctioneer school about the difference between how most people relate to rejection and how auctioneers are taught to relate to rejection. Spoiler alert, they’re different. And then she shares how she turned a simple but profound idea into a workshop, a TEDx talk, a movement, and now a book. So, buckle up. This one is juicy.


Here’s a little bit of her resume. She is a communications coach. She works with executives, VC-backed founders, and ambitious high-impact people. Her clients have included Salesforce, Google’s X team, and Dropbox and she helped Rio de Janeiro secure the 2016 Olympics. She has been featured on CNBC, Forbes, and Fast Company. Here we go.




Hilary Hendershott: Dia Bondi, welcome back to Love Your Money.


Dia Bondi: Hi, Hilary Hendershott. So nice to see you.


Hilary Hendershott: It’s our four-year reunion.


Dia Bondi: I know. So, we were just chatting before we hit record about you were the first podcaster professional woman with a podcast that I pitched the idea of talking about, at that time, project to Ask Like An Auctioneer, which is now a book. You were my first pitch and you got back to me in 40 seconds and said, “Yes, here’s my booking link.” And it was such a wonderful like validation that this crazy idea was interesting. It was a real kickstart moment for me at the beginning of this journey of writing a book that we’re going to talk about today.


Hilary Hendershott: Well, you do your research well because I, at the time, and I still don’t see many women talking about asking for more. I mean, I read research that women don’t ask enough and then I read rebuttals of that research. It’s very controversial. It’s not our fault, it’s the men’s fault who won’t give us the money.


Dia Bondi: I almost at this point, I also, when I talk to folks about bringing the workshop or the keynote somewhere, I talk to folks about being on their podcast or I talk to folks about the book, I often hear like, “Oh, women, they ask but they don’t get or women don’t ask enough.” And I’m kind of letting go about what the cases on that. I’m like, I don’t care. I actually don’t care. What I care about is if you are a woman with a pretty clear goal and you want to use asking as a success strategy, I want you to be able to ask for more and get it and never leave any money, or very importantly, opportunity on the table so that you can ask as strategically and as fruitfully as possible when you do.


Hilary Hendershott: I think about that as kind of the micro versus the macro. I’ve had people stop me at speaking engagements and say, “But what about the wage, what do they call it, the gender wage gap?” Right? And I said, “I mean, if you want to crusade against that, that’s fine but you also need to maximize your own income.” Right? It’s like I don’t know if the gender wage gap plays into your income but I know we can make it higher.


Dia Bondi: Exactly. Exactly.


Hilary Hendershott: Okay. So, most of the folks listening back in 2019, I’m going to assume it’s no longer freshly in their minds. So, let’s start with auctioneering school. Tell us what brought you to auctioneering school and what did that do?


Dia Bondi: So, I’ve been a leadership communications coach for a very, very long time. I helped Rio de Janeiro win the right to host the 2016 Olympics. I’ve worked with Nobel Prize winners, VC-backed founders, senior leaders in large global brands for years and years, helping them speak powerfully at really critical moments. And that has been very rewarding work but it’s intense. And there was a point in my career where I decided to take what I thought of as sort of a low-level working sabbatical where I just didn’t pursue new clients, didn’t accept new clients, and I spent a year focusing on what really mattered to me. Who am I now? What do I want? This happens to me about every seven years, and in that time, I got a little itchy, scratchy to learn something new, just to do something weird to just get out of the world that I’d built for myself so that I could look back at it with a little bit of a fresh eye. And my husband reminded me that years before that, I at a dinner table had threatened to do something that was on my bucket list, which was to learn how to really be an auctioneer.


Years before that, I had been volunteered by the fundraising committee at our preschool to be the auctioneer for our annual little fundraiser because all the other mommies and daddies and caregivers were like, “I’m not picking up the mic.” And I was like, “Well, I’ll pick up the mic.” And so, I did it that time. And weeks later at that dinner table, I was like, “That was super fun. I think I would like actually learn how to do it.” We were going around the table talking about bucket list stuff. Well, during my sabbatical, which was a few years later, my husband said, “Hey, remember that thing you said you’d do? Maybe now’s the time to do it.” And so, I looked up, “How do you become an auctioneer?” And it turns out there’s a thing called auctioneering school. So, I booked that and I went. And me and a hundred cowboys in a run-of-the-mill hotel on the side of the highway in Route 66 in the Midwest learned how to…


Hilary Hendershott: Was it literally Route 66?


Dia Bondi: Literally.


Hilary Hendershott: Okay.


Dia Bondi: We learned how to auctioneer everything from art to real estate to $5 box lots, cattle. It doesn’t matter. You’re just taking numbers and saying, “Sold,” right? I spent ten days doing that, which is probably ten days too long but I did come out of that knowing some very basics. And I thought, “What am I doing with this?” And I thought, “Okay. When I back home, I’m going to start doing fundraising auctioneering for a territory I care about as an impact hobby,” which is to do fundraising auctioneering for women-led nonprofits and non-profits that benefit women and girls. And a handful of fundraisers later, I was like, “Whoa, I’m learning some stuff here that a lot of the women I work with in the business context and entrepreneurship that could learn from.” That’s how auctioneering school happened and how I got into doing it.


Hilary Hendershott: Dia, is there any way you can tilt that pop filter so I can see your entire lovely face? Is that possible?


Dia Bondi: There I am. Hi.


Hilary Hendershott: Okay. Awesome. So, actually, now I’m curious. When you say you’re a communications coach, what were you actually doing before auctioneering school?


Dia Bondi: So, my work looked like private coaching for strategic projects like Olympic bidding. The circumstance in that space is a little different now. When I was doing that in those earlier days, multiple cities would throw their hats in the ring to try to be selected as a hosting city. So, I worked on a handful of Olympic bids. I was the backstage and communications coach, speaker coach I think of for large events like the Clinton Global Initiative that would host big events where the U.N. would show every other year they’d come and we’d have entrepreneurs and thought leaders, folks who were trying to solve the grand challenges on this planet, speak about their work in a very short and high impact time. And folks like that, they need to step on stage and make a real impact in a very short period of time but that also looked like skills workshops inside of organizations across industries. I’m industry agnostic, whether you’re talking about tech or finance or hardware across the board, and that looks like private coaching, ongoing coaching for lead. And it still does. This is still the beef of what I do every day. And these folks are looking to think about using their voice as a leadership tool, not just as an information transaction tool.


So, I work with folks who are usually sort of VP-level and above at large organizations. Some of my clients are folks like Salesforce, one of my large clients. I work with a lot of folks in the industry function there and in the events function as well because those are the places where leaders carve a path for their initiatives that they are leading and build a reputation and a leadership voice inside of the audiences that matter to them.


Hilary Hendershott: Well, I get the feeling you’ve said that before. And so, you say you helped Rio de Janeiro win the Olympic bid in 2016. You want to talk about ask…?


Dia Bondi: Yeah. Sorry. Go ahead.


Hilary Hendershott: No, that’s okay. Would you want to add clarification there?


Dia Bondi: Oh, yeah. So, the bid process happens seven years before a game actually is hosted.


Hilary Hendershott: Okay.


Dia Bondi: So, just want to be clear to folks that the campaign happens long before the hosting.


Hilary Hendershott: Understood. And so, you were doing that in 2016, did auctioneering school in 2019. So, it seems like this becoming a scientist of asking and getting, it seems like there’s a throughline. It wasn’t a hard right-hand turn for you.


Dia Bondi: No. I mean, look, and I just did a TEDx talk on this this year where I talked about this intersection. So, when clients work with me in my communication space and I’m fairly active in the world of helping women, women entrepreneurs, whether they’re, I mean, I love working with VC-backed founders but I always have space to work with women founders who are even looking for angel funding or are bootstrapping as well, that sort of I do that through the SheEO, which is now Coralus Network and some other places. But when clients come to me, they’re often and this shows up a lot of my skills workshops also, if we’re going to put together a compelling story and help you use your voice to lead for a particular moment where you need to instigate action in your audience, I’m always asking, “What is it that you want?” Like, what’s the action you’re looking for? And essentially what that is, is like, what are you asking for? Sometimes it’s investment, attention, engagement. In my skills workshops and private conversations, that ends up being a raise, a promotion, a certain client. So, the answer I always get when I ask that question is often, well, what do you think I can get?


And that’s a conversation I’ve had with thousands of clients, “What do you think I can get, Dia?” And I’d be like, “Well, I don’t know. What do you think you can get?” And we’d gave it all out and we’d build a story around that. When I started auctioneering many years later and, actually, I went to auctioneering school in 2016. Auctioneer for two years before it hit me that we could learn and deploy what I learned on stage into the way in which we ask for more and get it in our businesses and lives and leadership. When I started auctioneering, I saw that like, oh, what do you think you can get? Aims for a yes and then when we get that yes, we congratulate ourselves. But that’s not what we do when we go auctioneering. So, my two worlds of communications and auctioneering crashed together when I saw, oh, for years we’ve been going for yes. And when we got it, we thought we were hot sh*t. And now I see, “Oh, no. That’s not what we do as auctioneers. As auctioneers, we actually look for a no and we can’t sell anything until we get a no.”


If I said I’m opening the bid right now at $100 for this piece of art, and somebody put their paddle in the air and I said, “Sold.” What have I done? I’ve left money and opportunity on the table. But if I ask to get a no and somebody says, “No, not that,” and I negotiate down, I am sure I’ve left nothing on the table. So, the idea of asking like an auctioneer is to shift our gaze toward actively pursuing a no, being happy when you get it, and then having a conversation and finding that perfect intersection between what someone will say yes to and the ask that you made.


Hilary Hendershott: And this is a huge shift in thinking for most people. I mean, the idea of hearing no is paralyzing for some people.


Dia Bondi: It’s an existential threat.


Hilary Hendershott: It’s an existential threat. “I no longer belong to the pack.” And there’s a testimonial on your website, someone named Frankie. She says, “I’ve never been so excited to set myself up for rejection.”


Dia Bondi: I love her. That was the best piece of feedback I had. I was like, “Yes!” And that’s because, Hilary, and everyone listening that when we flip it and we say, “Oh, I got a no and negotiated down.” That means I’ve hit the ceiling of what’s possible. I can be proud of that. Now, there is always a gap between the yes and the no, what we want to go for. And usually, see, there’s a relationship between how much we ask for and how much courage we need to do it. Those two things are kind of tied to each other, right? So, if I only can ask for as much courage as I can muster in equal parts. If I’m going to make a three-unit ask, I need three units of courage to do it. If I’m going to make a 15-unit ask, that means I need 15 units and that’s way too, right? And what dictates how much courage we can muster is usually what we think we can get a yes to. I can get enough courage to ask for and I’m pretty damn sure that I’m going to yes to.


Hilary Hendershott: That’s really insightful to pull it apart that way.


Dia Bondi: And so, there’s a gap that lives between a mostly guaranteed yes. And folks who are listening might be like, “I don’t need a guaranteed yes.” I’m like, “Kind of.” You know, maybe you need to be 99%.


Hilary Hendershott: I mean, just really think about how many no’s you get, right? And that tells you how much you’re hiding from.


Dia Bondi: Totally, 100%. So, there’s a gap between what we think we can get a yes to, and that’s how much courage we can muster for some folks who might be like, “I need to be 80% sure,” and that’s enough sure for me to risk. I make the ask anyway. But most of us want to have more chance that we’re going to get a yes than a no. There’s a gap between that yes and then the inevitable no with the absolute maximum ask you’re going to make. We don’t make asks very often that are in that zone because that zone is a place I like to call the zone of freaking out. There’s that zone where your best friend says it’s time to raise your freelance rates and you’re like, “Oh my God, I could never do that.” Yes, exactly. So, the idea that Frankie says, “I’ve never been so excited to set myself up for rejection,” what she’s talking about there is in the book and in my workshops and keynotes, I go, “Okay. Asking like an auctioneer actually means asking to get a no, which is inevitably in your ZOFO, your own personal ZOFO, and everyone’s is personal. And it changes as you grow like what used to be ZOFO wish for me is not so ZOFO wish anymore. I have new ZOFOs, you know.


Hilary Hendershott: Right.


Dia Bondi: But I share nine insights that I got from the auctioneering stage that make it more possible for you to take the risk of getting a no that help you step into the ZOFO and that’s what Frankie’s talking about. She’s like, “I got the big idea as I got a few big ideas that make me go, ‘You know what, if I get rejected, everything’s going to be okay.’”


Hilary Hendershott: Oh, okay. Wow. I mean, clearly, Frankie relates to no like many people listening to this do not. So, no is an opportunity.


Dia Bondi: Yes.


Hilary Hendershott: So, of your nine insights, will you give us three of your favorites?


Dia Bondi: Yes. Yes, I will. Yes, I will, Hilary. So, these are things that I started to realize on the auctioneering stage because even on the auctioneering stage, I’m in my ZOFO. There’s moments where I’m like because being a fundraising auctioneer means that you sell things, you auction things off but sometimes you do something called a fund a need or just ask for direct pledges, and you don’t actually sell anything at all. You just say, “We’re here to raise money. Who’s in at $10,000? Raise your paddle if you’re going to give $10,000 tonight.” And then we go down from there. Okay. Maybe I got one or two paddles at $10,000, and then I go down and I say, “Who’s in at 5,000? Anyone going to pledge 5,000 tonight?” You’ve been to fundraisers like this, right? Somebody says, “Me. Me.” I got a couple of fives and then you go down and down and down until you’re down in the hundreds, right?


Hilary Hendershott: Right.


Dia Bondi: And there are moments where I’m like, “Yeah. Should I let it hang out there one more second? Should I stop at 250 or should I go for the hundreds? It feels kind of freaky to go for the 100s.” And I start getting like I can’t tell. Is it embarrassing? And I remember the things I started to learn that helped me be more okay with being rejected by 400 people on a live stage. And that is this. Okay, I’m going to give you my favorite thing. One is that people are irrational and if you don’t like that, your rationale for what they should say yes or no to is not your rationale for what you think you would say yes or no to. So, stop shopping from your own wallet. Stop deciding what other people are going to say yes or no to. Let them decide. Here’s an example. I sold and you’ll hear about this and I talk about this all over the place. I sold at auction for a large fundraiser in San Francisco, a one-night camping trip for the bidder and 11 of their friends for $55,000, doubled it twice. We thought there’s no way it’ll go for more than like 22. If I had stopped at 22 because that’s what we thought it should sell for, I would have left a pile of money on the table. On the flip side, I sold at auction this thing called a daguerreotype at an art auction a couple of years ago. It’s like this special photographic method of whatever. It’s supposed to be very important. And this artist was supposed to be very important, and it was going to, for sure, going to go for $10,000.


Hilary Hendershott: A daguerreo?


Dia Bondi: A daguerreotype. I don’t know. It’s just a type of photograph. It doesn’t matter.


Hilary Hendershott: This is like an NFT? Okay.


Dia Bondi: No. Actually, it’s not digital, but.


Hilary Hendershott: I’m offending some people who are listening. I should keep my mouth shut. Okay. So, the daguerreotype…


Dia Bondi: Sold for 4,500, less than half of what we thought it was going to and should sell for. Your rationale is not their rationale. All you can do is ask and find out. So, this is a very freeing idea for folks, I find. This is the thing that lets the Frankie’s of the world go, “Wait, like why do I think I shouldn’t ask for that?” That’s because that’s based on what I think something is worth or not worth but it’s not me to decide the worth is actually held by the askee, how they perceive the worth. So, you got to ask to find out. And if you get a no and negotiate down, awesome. You know exactly where they live. Second idea that I love so much. Can I keep going, Hilary? You want me to keep going?


Hilary Hendershott: Yeah. Are we on number two or number three insight?


Dia Bondi: We’re on number two. First insight is that people are irrational and that their rationale is not yours. Stop deciding for them what they should and will say yes to.


Hilary Hendershott: Just get out of their wallets.


Dia Bondi: 100%.


Hilary Hendershott: Get out of her calendar. You don’t know.


Dia Bondi: You don’t know. So, you’re going to get in your ZOFO and you’re going to ask and find out.


Hilary Hendershott: Okay. People are irrational. Number two?


Dia Bondi: Number two, big idea that I love. I was just talking about it today, and this is, no, I’m going to save that one for later. Number two, price is the measure of value, not a way to define your worth or worthiness.


Hilary Hendershott: Oh, thank you. How do I charge my worth? You don’t have a worth. What do you mean how do you charge your worth? You’re not selling your soul. Go ahead.


Dia Bondi: This is exactly right. And you know, it’s tricky because, yes, I want people to get paid. I want you to get paid what you’re worth. This is the story right now. Get paid what you’re worth. Okay. The street value of that daguerreotype was supposed to be $10,000 and it sold for 4,500. So, what’s it actually worth? It’s worth whatever somebody is willing to value it at and pay for it. It doesn’t inherently diminish or expand its worth, just like we are not inherently expanded or diminished in our worthiness because somebody else will pay you $100 an hour versus $200 an hour, period. I’ll just be real honest. I sometimes charge women founders who are bootstrapping a hyper-low bono rate, so they have a little bit of skin in the game. Like, Hilary, I could take my husband out for dinner one night. Okay. That’s like the rate.


Hilary Hendershott: I have a sense.


Dia Bondi: Other times, my same minutes, my same skill, go to organizations, global brands. That one engagement is a down payment on a house. Do you understand? So, what am I worth? Both. It doesn’t matter.


Hilary Hendershott: Right. That’s insight two.


Dia Bondi: Insight two. So, we’re going to recognize that what somebody will pay is just a signal of how they value something, not a way to measure our own worth and worthiness. That’s number two. That helps the Frankie’s of the world go like, “Oh, I can get rejected because it’s not about me. I can get that no. I can step to my ZOFO.”


Hilary Hendershott: It’s clear Frankie’s in play. She’s playing, right?


Dia Bondi: 100%.


Hilary Hendershott: It’s just a game like football.


Dia Bondi: 100%.


Hilary Hendershott: Get the no. Catch the ball.


Dia Bondi: Absolutely. And changing my mind. I was going to do a different third one but I’m going to pick this one, which is that you can be an agent for your purpose. This can help us step into the ZOFO a little bit and risk the no. Okay. So, the idea here is when I’ve done a lot of workshops and keynotes around this as like an auctioneer project that I launched in 2019, a lot of women I talked to say things like, “Man, I can negotiate…” Notice this is the first time I’ve said the word negotiate because I’m very specific about this is about asking. Negotiation happens after that. Okay. But they use the word negotiate. I have no problem negotiating a multimillion-dollar contract for my employer but when I go to ask for a fill-in-the-blank, I just lose my mind. It’s really hard for me.


Hilary Hendershott: It becomes personal.


Dia Bondi: Yeah. And so, when we get back in touch with the purpose that your ask is serving, sometimes it’s easier to step into our ZOFO because we are being a champion for that purpose. We are acting as its agent. I’m not asking for me. I’m asking for get this 20% raise or I got an extra bonus this year that puts me over the top for my child’s 529. I do this, this year and I make this big ask. It means that I’m going to get my own apartment for the very first time where I’m going to launch my new agency.


Hilary Hendershott: I love that reframe.


Dia Bondi: You know, this is about getting into relationship not with what it does for you but how it enables your purpose and then be an agent for that. I learned at auctioneering school that we’re not the buyer. We’re not the seller. We’re an agent for the seller. And it gives me enough distance to be able to say, “One more round. Who else is in at $1,000?” and be willing to get rejected publicly. We can use that in our own lives to think about how we can be an agent for that purpose, that thing that we’re trying to nurture. It’s kind of like when I go to auctioneer something or I go to a fundraiser, I’m there too. There’s like the thing we’re doing, which is raising money, and then there’s the thing we’re really doing, which is funding women’s lives while they go through and funding women’s households, single mother households, while they go through breast cancer treatment. You see what I’m saying?


Hilary Hendershott: And in terms of, I mean, let’s take the model of you being an auctioneer. You’re an agent for the seller. You know, potentially that seller could hire another auctioneer. There’s like other people who could slot into that position. But when you’re talking about your child’s 529 or your apartment or your nest egg, for the most part, ain’t no one filling in that role, right? And that’s the thing I keep trying to point out to, especially women, is if you don’t do it, probably, honey, no one will. And so, you can put your dreams up on a shelf, you can avoid the no, you can avoid the ZOFO for your whole life and it’s just going to lead to one inevitable outcome, right? And it’s all about avoiding either making other people uncomfortable or the outcome of you think other people don’t like you or resent you or don’t want you around or something.


Dia Bondi: This is a big deal right here is in my communications work, there’s a lot of intersections between my communications work and this. Folks come to me because they want to be more powerful on stage in a boardroom, in front of a large audience, in front of their buyers, whatever it is. And so often they are like as soon as they start to experience how powerful they can be, they back away from the flame. So, the question is sort of like, what is it for you to not just pick up power but also, what is it for you to actually tolerate your own power?


Hilary Hendershott: Oh, wow. That got big.


Dia Bondi: Like, when we ask for things that have an impact, when we tell a compelling story to set up the ask we’re about to make, being compelling and making a big courageous ask is actually a very powerful act and can put pressure on the relationship. Can you tolerate that? 100%, we want that pressure to be positive. One of the ideas inside of Ask Like An Auctioneer I talk about, you have to find the offer inside of your ask. You need to understand how somebody saying yes to you helps them advance what matters to them. This is not an empathy-free zone.


Hilary Hendershott: Right.


Dia Bondi: So, this notion that…


Hilary Hendershott: I thought you were going to talk more about the offer. I thought that was really juicy.


Dia Bondi: Yeah. I mean, the offer…


Hilary Hendershott: Because in every ask is always an offer. I mean, my offer is to be someone’s fractional chief financial officer or whatever. And that’s the price. The price we say it is the price but there’s an offer there. And so, I thought that was really juicy. And in partnership with the idea of being an agent for the seller or that offer which is going to get you into a really like I’m just making sh*t happen. That’s all I’m doing.


Dia Bondi: And how delightful. For me, for example, when I’m in front of an audience like at an art auction I’ve done a couple of for fundraisers, I have to think about what do people want in this moment? They want to be part of a radical act of collective generosity. They want to be perceived as an art collector. Maybe tonight’s the night they buy their first piece and stand up for this dream they have for themselves. Do you see? Like, we’ve got to recognize what they’re getting when they’re giving. I tell a story in the book about years ago, I went to this professional development experience where we did this sort of like discovery of like what they called typing, which was sort of like, what archetype do you fit into or is alive for you when you’re at your most compelling? Surprise, surprise. Mine was an eccentric and we had a homework assignment which was to go out for 2 hours to go walk around town. We were in a small seaside town and go get something for nothing. Like, have somebody give you their socks, get a ride in a classic car, have somebody buy you an ice cream. It was like you had to do something kind of daring in your archetype. Mine, I got to lean into my eccentricity.


And I ended up having a guy who was walking down the street with a bunch of his golf buddies. I stopped him, had a conversation, and asked him to pull 20 bucks out of his wallet and give it to me. And 20 bucks today, this is probably like 12, 15 years ago, it’s a weird thing to do. Just, “Hey, hi. Nice to meet you. What’s your name? Hey, give me 20 bucks,” I said. He was like, “What?” “So, yeah, give me 20 bucks.” Well, this guy, and you’ll hear the full story in the book, this guy I could tell this guy was the guy that wanted to be the funniest guy in the room. He’s the guy that is going to go on too long giving the toast at the wedding. He’s the guy that’s going to order for the table. And I realized in this moment that the only offer I had to make was to give him a great story to tell the ladies at dinner tonight, which is that some woman walked up to him on the sidewalk, asked for $20, and he did the boss move of giving it to her. And so, I offered to him. I said, “Look, you give…”


Hilary Hendershott: You realized all this about him just by looking at him?


Dia Bondi: I’ve been a leadership communications coach for too long. Unfortunately, I use this. Sensemaking is pretty good. But in that moment I was like, “Look, you give me my 20 bucks and you just bought yourself a great story.” He was like, “Here you go.” It doesn’t always have to be super material, right? It’s about what people’s drivers are. So, you are totally on to something there that when we combine the idea of being an agent for your purpose and also really digging deep and being clear about what the offer is inside of your ask, this can make your big, powerful ZOFO ask actually framed as an act of generosity.


Hilary Hendershott: Yeah. Okay. That got really philosophical. Thank you. And we covered what I wanted to ask about your TEDx talk. And we’re obviously going to have people buy the books. They want to get the other six insights. Can we transition a little to talking about how you built an idea into a book deal? You’ve been working on Ask Like An Auctioneer for years, and it’s kind of a small, I mean, it has huge impacts but it’s like a niche thing.


Dia Bondi: Weird little nichy thing. I know.


Hilary Hendershott: Yeah. Tell me, how did you even design that? What were the surprises? What were the lessons learned? Not that you’re looking back on it, right? Your book’s about to launch. You’re going, “Hilary, I now have to sell the damn book.”


Dia Bondi: Yeah, it is true. It’s funny. Like, it feels like the beginning. It’s like feels like a destination has been reached but it’s just creating a whole new beginning. So, I went, I’m going to go do a little linear storytelling here. Apologies, folks. But it’s been a slog. I don’t want to do the whole like, “And then this and then stars. The sky opened up,” because it wasn’t. It’s been an incredible march, one foot in front of the other. And using something I teach in the book, which is that I had to fall in love with my goals way more than the torture of doing the work to make it come to life.


Hilary Hendershott: Yeah.


Dia Bondi: Like, I had to actively look at this little project and fall madly in love with it so I’d stand up for it over and over and over again. And it’s a slog but there are a couple of moments that were really critical. One is this wasn’t like I was sitting around going, “What should I write about?” I went to an all-day summit for the Coralus Network, which used to be the SheEO Network. Folks can find that on the Internet. It’s women supporting women entrepreneurs. And I was like, “Gosh, man, it would be so cool if all the women we support in that network.” Instead of asking the way that we do all the time, like if they had the chance to stand in front of a room and like learn how to auctioneer, just like as a way to experience that. I was like it’d be so cool not just that they could wear a gown and point at people in the room and say, “You, sir, you’re in at 43,000,” but instead like just that feeling of not having to just to come out with it and be real direct and it’s a really tight period of time so you don’t have a lot of time to mess around and get in your head. The numbers are the numbers and then that’s it. You get the no and then you sold. Move on 2 minutes later.


But I wasn’t going to start an auctioneering school for girls. Okay? So, I was like, well, I don’t want really women to know how to auctioneer. I just want them to start asking. And the way they think about going back to this when they have an audience, apart from that’s going to help advance whatever they’re working on when they go to craft the asks that matter and then build a story around that, then instead of asking like we always do, to ask like an auctioneer. And I was like, “Wait.” And I literally wrote that down, ask like an auctioneer. And I was like, “What does that actually mean?” And then for myself, I was like, “What do I mean?” And then I wrote the model, which you’ll see in the book too. It’s a little line graph that shows the vertical and horizontal axis relationships between the size of an ask and the courage you can get, where the ZOFO is, and where the no really lies. And then I was like, “Okay. That’s what it means to ask like an auctioneer.” And I was like, “How is it that I’m able to now, even in my business, be in my own ZOFO?” And I was like, “Well, because here are the things I learned.” I wrote down the eight or at that time was like six ideas/insights from the auctioneering stage. Then I had this thing sitting here. I was like, “Well, that was weird.” A couple of weeks later and you know that thing…


Hilary Hendershott: I think of the download. Now, what the heck do I do with it? I don’t think I want to be burdened with this responsibility.


Dia Bondi: I was like, “What do I do?” And I was like, “Okay. Dia, just slow your roll. Just sit with it for a minute.” And it’s sort of like when you’re shopping for a certain car, you see that car everywhere or for those of you who are listening, who have been pregnant before, maybe you’re pregnant, and then all of a sudden it’s like, “There are pregnant people everywhere.” No, they were always there. It just got into your awareness. So, I just carried it around for a while and I started seeing opportunities to talk about it. And I had this woman invite me to give a little talk at a Silicon Valley meet-up. It was unpaid. There would be 60 women in the room. They were all sort of like early to mid-career folks. It was just a Silicon Valley meet-up and they wanted me to come talk about communications or something. And I was like, “No, I want to come talk about this crazy idea I have called Ask Like An Auctioneer.” She said, “Great. You have 20 minutes.” So, I stood in front of the room and I said, “All right. I’m a leadership communications coach. It’s kind of boujee. I work with a lot of really high influential people. I’m not going to talk about that today. Who cares? What I want to talk about is you and this wild idea that I have called Ask Like An Auctioneer and your job is to do this one thing. At the end, you need to tell me if it’s bullsh*t or not. And every woman at the end of the session raised their hand and said, “Please keep doing this.”


Hilary Hendershott: That was brave by the way.


So, I was like, okay, I’m on to something. And then I basically open-sourced it, Hilary. And this is my advice to folks. When you have a crazy idea, open source it, get it in front of people, and let them tell you what’s resonant and not resonant, and let that tell you what your next step is. So, I spent the next year saying, “Thanks so much for your inquiry. Oh, you really are having a meet-up. Can I take 20 minutes and talk about this thing?” And I just put it in front of people. Somebody asked me to come give a workshop at Dropbox and I was like, “What do you want me to talk about?” And she was like, “All this stuff.” And I was like, “No, actually I want to talk about this stuff.” And she said, “Great.” And I didn’t even have a workshop yet. I said, “I’m going to turn this idea that I’ve been talking to these folks with into a workshop that was 2 hours and I’m going to charge for it this time.” I ask like an auctioneer, and they said, “Ooh, we can’t have budget for that.” I was like, “Yes, I hit the no. That’s good. What kind of money do you have?” They told me and I had these moments where I let my audiences fund the development of these ideas.


Hilary Hendershott: It’s very meta that you’re asking like an auctioneer to teach like ask like an auctioneer.


Dia Bondi: 100%. So, I go out. I did workshops at Alphabet’s X team, we did it at Latinas in Tech a few times. LTX Fest. We did it at Women of Color Advancing Peace and Security. I did it at a couple of architecture firms. I would talk to everybody. I did it on the Hilary Hendershott’s podcast. You were the first person I reached out to. You were part of my experiment.


Hilary Hendershott: Thank you. Love it.


Dia Bondi: And now I put it up on a website. Then I started talking about it in my newsletter, and then I had put it in front of a coach friend of mine and she used to own a publishing company. She said, “That is a book, Dia.” And in that, I always knew it was out there. When I knew what it was, when I was really clear about what the ideas were that worked and what was kind of like superfluous, I started to go like I think it’s time to put together a book proposal because I know what some folks I think use writing a book as a way to develop the ideas.


Hilary Hendershott: Yeah.


Dia Bondi: I developed the ideas first and then I basically took my two-hour workshop and turned it into a book. And by then, I had hundreds of anecdotes, hundreds of Frankie’s that I could draw on, you know, which made writing the book proposal, which, by the way, was 68 pages long.


Hilary Hendershott: Holy cow.


Dia Bondi: Oh, yeah. Nonfiction book proposals. No joke.


Hilary Hendershott: That’s basically the book.


Dia Bondi: Yes, it was but not too hard because I was like, “I know what my ideas are that I’m going to share. I know what six-step strategic ask framework I’m going to share,” because I developed it to do workshops for it.


Hilary Hendershott: You’ve been iterating it for years.


Dia Bondi: 100%. So, I had a friend and I’m just about to the end of the story. I had a friend who I work with sometimes and I bring her into some of my communications work to be a writer for me, and she helped me refine that. And then I went out and started asking like an auctioneer and pitching to agents that were too big for my shoes. Okay. Is that an expression?


Hilary Hendershott: Yeah. No, their shoes were too big for you but it’s fine.


Dia Bondi: Thank you. Thanks so much.


Hilary Hendershott: I’m teaching my seven-year-old how to get it contextually, so I got it contextually.


Dia Bondi: Got it. Cool. So, this was it, everybody. I asked to get rejected, and then when I got rejected, I was like, “Oh, okay. Not that one.” I asked in order to get rejected. If I had made the safe asks, I would have been playing low.


Hilary Hendershott: Right. So, circling back to the idea of being an agent for your calling or your mission, I mean, and this whole idea of experimentation is just another way of getting into play.


Dia Bondi: 100%. Get into motion. I have a huge bias toward action.


Hilary Hendershott: Because that’s where people get heavy and significant if it means something.


Dia Bondi: Yes. I just finished listening to Big Magic. And in that book, she talks about sort of living a creative life and how making things in the world has to both be extremely important and not important at all. You have to take it extremely seriously and hold it lightly at the same time. And that’s kind of when I think about being an agent for this book. I was its agent advocating for its birth into the world everywhere. And I could do that like I do for my kids. My kids know I will cut someone for them. This book knows. This project knows I will cut somebody for it, with love.


Hilary Hendershott: Do you want to say anything about the final or the way you – because you went out to publishers to try to get a no. Do you want to say anything about the final yes?


Dia Bondi: Yeah, I got rejected and rejected and rejected. And then actually the writer friend of mine was like, “Actually, I’m a ghostwriter for this agency and they do publishing navigation.” And we got connected and he said, “I could sell this.” And then we were off.


Hilary Hendershott: Lovely.


Dia Bondi: It was weird.


Hilary Hendershott: No. It was the universe having your back. It wasn’t weird. It was exactly what was going to happen. Well, I think we should put a pin in this here because we gave birth to the big baby in this conversation. And now, Dia, we all know you have to go sell the book.


Dia Bondi: I do.


Hilary Hendershott: So, you need to store up your energy for that project. So, the book will be live I think I read in November. Is that correct?


Dia Bondi: Correct. November 14th. Right now, it’s available for preorder. If you preorder it now, you can go to AskLikeAnAuctioneer.com and find the online retailer of choice and make that purchase. And then you can go back to AskLikeAnAuctioneer.com and you can get some preorder bonuses there and it’s super easy. You don’t have to remember any numbers. You just tell us where you bought it. We trust you. And then right after November 14th, it’ll arrive on your doorstep.


Hilary Hendershott: Awesome. And I did preorder the book.


Dia Bondi: Thank you.


Hilary Hendershott: I’ve seen your framework emails and amazing killer short valuable videos of you. So, thank you for all that. Well, I guess 2027, this is our four-year anniversary. You’re going to have to come back to the show in 2027 and give us the what’s up since from here until then, since then until now. I can’t even say it but you know what I mean. Thanks for being here, Dia.


Dia Bondi: I love it. Thank you so much, Hilary. And, everybody, go ask like an auctioneer. I can’t wait to see.


Hilary Hendershott: Ask like an auctioneer.


Dia Bondi: I can’t wait to see what it does for you.


Hilary Hendershott: But first, buy the book.


Dia Bondi: Thank you.


Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.


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