149: Dia Bondi – Ask Like an Auctioneer

Guest: Dia Bondi

Guest Bio:

Dia Bondi is a Communications Catalyst for high-impact people. In her private coaching and programs, she works with C-level leaders, VC-backed founders, and ambitious professionals, helping them find their voice and lead with it. Her workshops and talks are hosted by corporations including Quartz, Salesforce, Google’s X-team, and Dropbox. In global sport, she helped Rio de Janeiro secure the 2016 Summer Olympics. After attending auctioneering school for fun, she translated the techniques she learned into a program that prepares ambitious professionals, and especially women, to ask for more and leave nothing on the table, called Ask Like an Auctioneer. She’s been featured on CNBC Make It, Forbes, and Fast Company. Her book, Ask Like an Auctioneer: How to Ask for More and Get It, is available now.​

Key Points:

Dia’s Backstory & Career Path

Started her career in fitness, where she loved helping people feel powerful and embodied. Then, transitioned into training and development (professional development) after college. She discovered her passion for storytelling and communication while observing a workshop for finance leaders. Dia founded Dia Bondy Communications in 2009 to help leaders and VC-backed founders communicate effectively in high-stakes moments.

"Ask Like an Auctioneer" Concept
Inspired by her side work as a fundraising auctioneer. The key principle: ask big enough to get a “no”, because a “no” signals you’ve reached the upper limit of what’s possible. In business, people often limit their asks based on what they think they can get, leaving money and opportunity on the table. Instead of selling to the first yes, push further to uncover maximum value.

Overcoming Fear of Asking

Fear of rejection keeps people from asking boldly. Many assume rejection damages relationships, but often it doesn’t. Leaders should teach teams that discomfort (the Zofo—Zone of Freaking Out) is a signal of courage and potential growth. Reframe rejection: it’s information about value, not a judgment of personal worth.

Lessons from Auctioneering for Business & Sales

· Price = a reflection of value, not worth. The same item can sell for vastly different amounts depending on the audience.

· Know your “reserve.” Like an auctioneer’s minimum acceptable price, know your bottom line before asking.

· People are irrational. Decisions are often emotional, even in data-driven environments—so storytelling is critical.

Four Types of Asks That Drive Growth

1. Money – dollars, budgets, contracts.

2. Influence – visibility, access to networks, platforming yourself.

3. Authority – positioning yourself to make important decisions.

4. Balance – aligning deals and clients with the kind of work you actually want.

Why People Struggle with Asking

Fear of rejection. Lack of clarity on what to ask for and when to ask. Sometimes people make asks that are too small, too vague, or to the wrong audience.

Framework for a Strategic Ask (first 4 of 6 steps)

1. Define your main concrete goal.
2. Identify the next big move toward that goal.
3. Determine the ask that advances that move.
4. Ensure the ask is big enough to risk rejection.

Storytelling Framework: “Blocker Buster”

1. What your audience wants.
2. What’s blocking them from achieving it?
3. How do you remove the blockers?
4. Your ask (to move them forward).

Big Takeaways

• Asking boldly is a skill that can be learned.
• The most powerful ask live in the Zofo—the zone of freaking out.
• Rejection is not failure; it’s valuable feedback about what the other side values.
• Asking strategically, with courage and clarity, maximizes opportunities for growth, influence, and alignment.

Guest Links:

Connect on LinkedInCon

Connect on Instagram

https://www.diabondi.com/salesology

Download The Powerful Ask Plan, a free tool to help you design a strategic ask.

About Salesology®: Conversations with Sales Leaders

Download your free gift, The Salesology® Vault. The vault is packed full of free gifts from sales leaders, sales experts, marketing gurus, and revenue generation experts.

Download your free gift, 81 Tools to Grow Your Sales & Your Business Faster, More Easily & More Profitably. Save hours of work tracking down the right prospecting and sales resources and/or digital tools that every business owner and salesperson needs.

If you are a business owner or sales manager with an underperforming sales team, let’s talk. Click here to schedule a time.

Please subscribe to Salesology®: Conversations with Sales Leaders so that you don't miss a single episode, and while you're at it, won't you take a moment to write a short review and rate our show? It would be greatly appreciated!

To learn more about our previous guests, listen to past episodes, and get to know your host, go to https://podcast.gosalesology.com/ and connect on LinkedIn and follow us on Facebook and Instagram, and check out our website at https://gosalesology.com/.