Great Questions Can’t Overcome Poor Delivery

Welcome back to the 33rd issue of Disrupting Conversations!

There’s nothing like good old-fashioned film study—the tape doesn’t lie. 

I recently reviewed a sales conversation that hinged on a single inflection point, one that could have been a complete home run but instead left me cringing. Not because the salesperson did anything explicitly wrong, but because of how they approached their questioning. 

Their prospect had just shared some impressive business results—the kind that most companies would love to achieve—and shared their desire to double down next year. 

But instead of acknowledging that success, the salesperson immediately fired back with a critical "How are you going to do that?"

The silence that followed was deafening. 

This exchange highlighted something I've observed over decades of coaching: We often miss opportunities to build trust because we forget about empathy. 

Not the “sugar-me sweet” frosting on a cake type of empathy, but the purposeful, “I know this will be tough” type. Sometimes we're so focused on getting information or moving the conversation forward that we fail to acknowledge the human being in front of us.

Today, we’re talking about why empathy is crucial for meaningful conversations, how its absence can derail even the most promising interactions, and what you can do to stay focused on the person across from you.

Breaking Sales is my podcast to connect with those who are ready to break free from the chains of old sales methodologies that don’t work.

Title of Episode: Start Your Conversations With More Trust

🎙️Your prospects are constantly bombarded by sales pitches. As a result, they've developed powerful filters to quickly determine which conversations might help them and which ones could waste their time. This reaction isn't just learned behavior—it's primal, rooted in survival instincts that date back tens of thousands of years. Even when you come highly recommended, prospects may still approach your first interaction with skepticism.

This is exactly why empathy is so crucial in those early moments. In this episode of Breaking Sales, Pam and I explore how to level the playing field with prospects and clients. We discuss why really good questions can sometimes backfire, and how leading with genuine empathy can help both parties enter conversations with more courage and curiosity.

Great Questions Can’t Overcome Poor Delivery

Think about the last time someone asked you a direct question—especially someone you didn't know well. 

What went through your mind? 

If you're like most people, you probably found yourself in defense mode, wondering: Why are they asking this? Where are they going with this? Are they going to judge my answer?

This internal filtering happens lightning-fast and often unconsciously. But it profoundly affects how much we share and how honest we're willing to be.

That's where empathy comes in. 

When someone shows genuine empathy—taking a moment to acknowledge your experience or perspective before diving into their questions, they help lower those natural barriers.

Consider these two approaches to the scenario I mentioned in my opening note:

Approach 1: "How are you going to do that?"

Approach 2: "That's impressive. What's been the secret to making that happen?"

Both questions aim to understand the company strategy, but the second approach acknowledges the achievement first. 

It shows you're not just extracting information—you're genuinely interested in understanding their success.

This principle applies far beyond sales. As a parent of four, I've learned (sometimes the hard way) that when I need to have tough conversations with my kids, starting with empathy makes all the difference. 

Before pointing out why a decision might be unwise, acknowledging their desire for autonomy and the opportunity to find their own path creates a foundation for actual dialogue. I’ve noticed how they settle in more and seem to listen to my advice with more objectivity than skepticism. I’ve also observed how their body language changes from closed to open.  

👉Remember: Empathy doesn't mean avoiding difficult questions. In fact, some of the most powerful questions make people think deeply or venture into uncomfortable territory. But when we lead with empathy, we create the safety necessary for honest exploration and authentic answers.

The next time you need to ask deeper discovery questions—whether in sales, leadership, or family conversations—pause first. How can you acknowledge the other person's perspective or experience before diving in? That small shift might make the difference between resistance and openness.

Thanks for reading!

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