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.