Every leader faces those moments that can make or break an opportunity. It may be asking for a raise, pitching a big idea, or addressing a room full of decision-makers. These high-stakes conversations require the ability to communicate with confidence! In this episode of The Leadership Habit Podcast, host Jenn DeWall sits down with Dia Bondi, a communications catalyst and author of Ask Like an Auctioneer: How to Ask for More and Get It. Together, they explore what it takes to prepare for those defining conversations where trust, influence, and outcomes are on the line. Whether you’re negotiating resources, inspiring your team, or advocating for change, Dia’s frameworks and insights reveal how to speak powerfully and how to be “absolutely clutch in clutch moments.” Meet Dia Bondi, Communications Catalyst Dia Bondi is a keynote speaker, coach, and communications expert who helps leaders and changemakers speak with authenticity and authority when it matters most. Her clients include global brands like Nike, Meta, Salesforce, and Dropbox, as well as entrepreneurs, executives, and athletes seeking to elevate their presence in high-pressure situations. As the author of Ask Like an Auctioneer: How to Ask for More and Get It, Dia combines storytelling, neuroscience, and negotiation strategy to help people push past fear and unlock their boldest communication potential. Her work has been featured on CNBC, NPR, and Forbes, and she’s known for helping professionals deliver messages that move audiences to action. Why High-Stakes Conversations Matter As Bondi explains, high-stakes moments aren’t just about closing a deal or landing a promotion; they’re about leadership itself. These are the situations where your communication can unlock decisions, resources, or opportunities that move your business and career forward. A high-stakes conversation could be a one-on-one with your boss, a pitch to a major client, or a keynote at a conference. What makes it high stakes is the combination of risk, visibility, and impact. These moments require you to build trust quickly, communicate with purpose, and guide others toward a decision. “Every high-stakes moment,” Bondi says, “is really an ask. You’re asking for engagement, for a decision, or for action, and how you prepare for that ask determines the outcome.” The Most Common Communication Mistakes In her two decades of coaching executives, startup founders, and leaders, Dia has seen several recurring missteps that undermine even the most talented professionals. 1. Rushing Through the Story Too often, leaders jump straight to the solution, listing features, metrics, or data, without slowing down to paint a compelling picture of why it matters. “The most powerful communicators,” Bondi explains, “don’t just describe a product or proposal. They invite the audience into a vision of what’s possible.” By taking time to describe the problem, future, and stakes, leaders create emotional engagement and tension that make the solution more valuable. 2. Focusing Only on Themselves Nerves and pressure can cause people to over-focus on their own objectives, like what they need, want, or fear. But as Bondi reminds us, “communication isn’t just about information transfer. It’s about connection.” Compelling storytelling shifts attention to the audience: their desires, frustrations, and motivations. When people feel seen and understood, they’re more likely to say yes. 3. Playing Too Small Many professionals limit themselves by asking for too little. Bondi challenges leaders to “ask big enough that you might get a no.” This approach, inspired by her experience as an auctioneer, helps leaders stretch beyond comfort zones and uncover what’s truly possible. If you get a no, you’ve found the boundary. If you get a yes, you’ve just achieved more than you thought possible. Building a Strategic Ask Behind every effective communicator is a strategic ask, a clear understanding of what you’re requesting, who you’re asking, and when the timing is right. Bondi encourages leaders to check three elements before entering any high-stakes moment: The Right Ask: Are you requesting something you don’t already have? Don’t waste time asking for permission or support that’s already been given.The Right People: Identify who truly influences the decision. Sometimes it’s not the top decision-maker but a trusted ally who can advocate on your behalf.The Right Timing: Consider the broader context, including market conditions, organizational priorities, or competing pressures. The right message delivered at the wrong time can still fall flat. When you align these three factors, your message lands with far greater impact and credibility. Storytelling Frameworks That Work Under Pressure Dia Bondi’s genius lies in turning complex communication strategies into simple, repeatable frameworks. Two of her most powerful tools are the Blocker Buster and the ...
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