Speaking with Power and Authenticity in High-Stakes Deals with Dia Bondi

In this episode of the DealQuest Podcast, I sit down with Dia Bondi, a communications catalyst who works with C-level leaders, VC-backed founders, and ambitious professionals to help them find their leadership voice. After helping Rio de Janeiro secure the 2016 Summer Olympics, Dia attended auctioneering school for fun and translated those techniques into programs that prepare professionals to ask for more and leave nothing on the table. Her book Ask Like an Auctioneer: How to Ask for More and Get It and her "Ask Like an Auctioneer" methodology have been featured on CNBC, Forbes, and Fast Company.

What struck me most about this conversation was how Dia's approach to communication mirrors what I've learned about negotiation over 35 years. When you haven't done the internal work to understand who you are and what you bring, no amount of tactical training will help you succeed in critical moments. Whether you're pitching to investors, negotiating an M&A deal, or securing a strategic partnership, the difference between success and failure often comes down to your ability to show up authentically while being strategic.

From Daisy Duke to Deep Connection

Dia's childhood dream tells you everything you need to know about what drives her work today. She wanted to be a long haul truck driver, inspired by Daisy from The Dukes of Hazzard. Not because of the truck itself, but because of what it represented: adventure and the element of surprise. You'd see this polished chrome 18-wheeler pull into a truck stop, windows obscured, and when the door opened, out would step someone unexpected.

That vision captures the essence of powerful communication. When you look back at what you wanted as a kid, you often find the core drivers that show up throughout your career. For Dia, those drivers were adventure and deeply connected experiences. Today, whether she's script writing with senior leaders for an Olympic bid or coaching a founder through a critical funding pitch, those same elements are present.

The Million-Dollar Deal That Changed Everything

Dia's first transformational deal happened when she stopped leaving money on the table. For years, she'd been writing standard contracts for her work with VC-backed founders. Then she realized something: just because she wasn't a formal advisor didn't mean she couldn't ask for equity.

She tested it with one client, proposing a mix of cash and shares instead of her usual fee structure. That $30,000 project turned into over a million dollars when the company succeeded. But what made it truly transformational wasn't just the money. It was that the deal had the same feeling as selling those shiny rocks to her neighbor Ms. Alkermer when she was a kid. Both parties were delighted. Everyone had skin in the game. The relationship deepened because the structure aligned their interests.

This is the kind of thinking that separates professionals who grow wealth from those who just earn fees. When you understand that compensation can be structured in ways that create asymmetrical upside, you open possibilities most people never consider.

The Real Stakes in Communication Work

Dia doesn't take on every client who applies to her programs. She looks for one thing: stakes. Are there actual stakes? Because the work she does isn't about skills-based communication training. It's not about where to put your hands or how to do a dramatic pause.

There's a quote from Miles Davis that captures this perfectly: "It takes a lifetime to sound like yourself." The difference between a fabulous trumpet player and Miles Davis isn't technical skill. It's whether his voice comes through the music he plays. The same applies to leadership communication. The difference between a skillful communicator and someone with a true leadership voice is you.

When stakes are present, whether it's a singular critical moment or a phase in your business where your voice will determine outcomes, that's when this work matters. If you're heading into a funding round, negotiating a partnership, or positioning yourself for the next stage of growth, your leadership voice becomes a strike point that drives decisions and secures resources.

The Six Attributes of Clutch Communicators

Dia has identified six attributes that show up consistently in people who are absolutely clutch in high-pressure moments. You can evaluate yourself on a scale of one to ten for each attribute to identify where to focus your development.

First, the willingness to be big in big moments. This doesn't mean being loud or demonstrative. It means making the more courageous choice. One of Dia's clients had to paint a detailed Technicolor picture for her audience, which felt uncomfortable. But she did it anyway, and that willingness to expand beyond her comfort zone helped her close the deal.

Second, knowing your voice. This means understanding what's important about your origin story in terms of drivers, not resume items. It means knowing your operating principles and leadership philosophy. Most leaders do things that feel so natural they don't even realize it's a leadership approach. But when you can name and claim these elements, they become tools you can deploy strategically.

Third, asking strategically. Clutch communicators don't make anemic, wimpy asks. They craft meaningful asks that create value for everyone involved. These aren't single-item requests. They're often a kaleidoscope of things that together create something valuable in the market or in a deal.

Fourth, having killer setups. These are frameworks you can use repeatedly to set up your asks in ways that align with your voice and use your natural language. Dia custom builds these with clients based on their leadership voice.

Fifth, bridging beautifully. This means recognizing that you are not your venture. Whether you're an in-house professional or a founder, your unique voice and perspective exist separately from the specific thing you're building right now.

Sixth, prepping like a pro. Dia's best clients don't just come to sessions to talk about what they're going to do. They actually do it. They rehearse their pitches, practice their setups, and test their language out loud.

Understanding Strategic Asks That Create Value

Understanding what you're truly asking for requires time and thought. You need to go beyond the surface request to what you really want. One of Dia's clients thought his ask was to be invited into a conversation about a secondary deal between early investors. But when Dia pushed him on what would happen if they said no, he admitted he'd insert himself anyway. That made it a demand, not an ask. The request was simultaneously too cold (trying not to overstep) and too hot (prepared to force his way in regardless).

After spending an hour working through the full dynamics, they identified that his real ask was multi-layered. It involved positioning himself in the conversation, establishing how they'd arrive at the price, and determining who would be involved in the process. With a killer setup and the right ask, he maneuvered the entire deal over one to two months. That initial insertion into the conversation made everything else possible.

The Mirror Effect Setup

One powerful setup Dia uses is the "mirror effect": I see you, you see me, and because of that, here's my ask. You start by demonstrating that you understand what the other person is up to, what's important to them, what's going on in their business, and why certain outcomes matter to them. Then you reveal where you're going and what you're building. When you show where these paths intersect, that intersection becomes the natural place for your ask or offer.

This approach requires slowing down the conversation to paint a picture. It takes courage because it's easier to rush through features and benefits. But when you can articulate the tension someone else is operating in without making them feel exposed, you create an opening for real conversation. If you can recognize and give language to how stuck somebody else might feel but doesn't want to say it, that's powerful. You don't need to say "you're really stuck," but you can find ways of making it clear that you understand the tensions they're navigating.

Bridging Your Voice to Your Venture

The ability to bridge elegantly matters because you might run a fund today, become a founder in three years, and an advisor ten years after that. You're still you. You just need to bridge to each of those things you're working on.

Dia worked with a fintech founder who realized that while he was building fintech products, what he really cared about was something he called autonomous finance. That concept informed his product decisions and leadership approach, even though it wasn't the product itself. When he learned to bridge elegantly between his vision for autonomous finance and the specific products his company was building, his communication became more compelling. People could see both what he was building and the unique perspective he brought to it, which helped answer the critical question in any deal: why you?

The Summit That Secured $10 Million in Value

Another client was convening a summit to get both sides of her data platform to say yes to participating in an industry governance structure for building something together. No money would change hands. The ask was purely about securing a decision to engage.

When she told Dia the ask was to "engage in this initiative," Dia pointed out that everyone was already in the room. They'd already said yes by showing up. That ask was too cold. The real work was figuring out what to ask for next, which required understanding what she truly wanted them to commit to beyond just attendance.

The setup became the critical piece. Using the story of how Visa was built by industry partners who came together to create infrastructure rather than a product, she painted a picture that helped everyone recognize the moment they were in. Before moving to the next part of the story, Dia made her paint more picture, tell what that really meant, describe the feeling in the industry at that time, and give three specific examples with numbers. The client is an ex-military veteran turned data scientist who naturally prefers minimal words, so this was uncomfortable. But she decided to show up big in that big moment.

After the summit, people came up to her emotional about recognizing the opportunity they had to create long-tail impact. Everyone in the room committed to the initiative. She estimated it created about $10 million in value for the business.

Why "Be Authentic" Is Useless Advice

When clients tell Dia something doesn't feel authentic, what they often mean is it doesn't feel familiar. This is a critical distinction. Expanding your range so you're not limited to what feels exactly like your current comfort zone is essential for showing up clutch in high-pressure moments.

If you know your voice, if you know what you're after, if you're totally in your own body in these high-stakes moments because you understand who you are, then even when something is unfamiliar, you can stick with it. Inauthentic becomes a trap word that keeps people small.

You also can't coach someone by telling them to "just be authentic." It doesn't mean anything actionable. The six attributes Dia identified are tactical and touch high-level concepts, but they give you something concrete to work on. You can evaluate where you are on each attribute and choose which one to develop next.

The Power of Seeing the Other Person

Taking the time to honestly see where the other person is coming from, understanding they're operating in a different world with different pressures and objectives, changes the dynamic entirely. People often skip over the "I see you" part or deliver it as lip service. But when you truly understand that someone is stuck, operating in uncomfortable tensions, or trying to serve multiple masters, and you find a way to acknowledge that with a level head in a pragmatic way, it creates space for real conversation.

This connects back to making the choice to be big in big moments. Slowing down to paint that picture is where transformation happens. It's easy to just talk about features and benefits, but recognizing the tensions someone else is navigating and speaking to those with honesty and pragmatism creates the foundation for deals that work for everyone.

Prepping by Actually Doing It

What you think you're going to say and what actually comes out are shockingly different. Your internal experience of yourself is not other people's experience of you. You might walk out of a meeting thinking you bombed when you actually did well, or think you nailed it when you missed the mark entirely.

Productive prep doesn't mean spending days on preparation. It means using your prep time efficiently in ways that align with who you are and support your voice. Even 15 minutes can be highly productive if you're actually testing your setup rather than just thinking about it. Dia's best clients have learned that they don't just come to sessions to tell her what they're going to do. They actually do it in the session so they can see how it sounds and adjust accordingly.

Listen to the full episode to hear Dia break down her complete approach to finding your leadership voice and using it strategically in the moments that matter most for your business.

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FOR MORE ON DIA BONDI
LinkedIn: https://www.linkedin.com/in/dia-bondi/
Company: https://www.diabondi.com/
The Book: https://www.asklikeanauctioneer.com/

FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!