Quit Asking the WRONG Sales Questions

Selling gets easier when you stop talking your way and start communicating theirs—because comfort, not pressure, is what actually closes deals.

If you want better sales results, stronger client relationships, and fewer stalled conversations, there’s a place we have to start—long before the proposal, the pitch, or the follow-up. You have to understand who you’re talking to.

Not demographically. Not generationally. Not by income bracket or job title. I’m talking about how people are wired to communicate.

Over decades of working with sales professionals, leaders, and teams, I’ve seen this pattern repeat itself over and over again: most salespeople don’t struggle because they lack skill or motivation. They struggle because they ask the right questions to the wrong personality.

The Two Buyers You’re Always Selling To

While no model is ever perfect, most buyers lean strongly toward one of two communication styles.

Relators are relationship-driven. They care about connection, trust, and comfort before they care about numbers. They want to know who you are. They ask about your family. They share stories. They build rapport through conversation and shared experience.

Bottom Liners are task-driven. They value efficiency, clarity, and results. They want facts, data, timelines, pricing, and outcomes. Small talk feels like friction. Emotional storytelling feels unnecessary. They’re not here to be your friend—they’re here to make a decision.

Here’s where sales often goes sideways.

Most of us naturally sell the way we prefer to buy.

That means Relators sell warmly, conversationally, and emotionally—often overwhelming Bottom Liners. Bottom Liners sell quickly, logically, and directly—often alienating Relators. And the cost of that mismatch is enormous.

When you communicate only from your own style, you instantly lose connection with roughly half the people you talk to. Half of the world doesn’t speak your communication language—and they don’t need to. You do.

The First Step: Know Yourself

Before you can adapt to others, you have to be honest about who you are.

I’ll go first. I’m a Relator. I love people. I ask questions. I connect dots. I build instant rapport. And early in my career, I couldn’t figure out why some incredibly qualified prospects seemed irritated by me.

It wasn’t because I wasn’t competent. It wasn’t because my offering lacked value. It was because I was overwhelming Bottom Liners with warmth when what they wanted was clarity.

Once I understood that, everything changed.

The Million-Dollar Question

There is one simple question—easily adapted to any industry—that tells you almost everything you need to know about how to sell to someone.

It sounds like this:

“We’re meeting to talk about my proposal, and we can do this a couple of ways. I know you’re busy, so I could come by, walk you through the information, answer questions, and be out in about 15–20 minutes. Or, if you prefer, we could grab lunch, get to know each other a bit, and talk through things more conversationally. What works best for you?”

Their answer tells you exactly how to proceed.

If they choose lunch, conversation, or connection—you’re working with a Relator.
If they choose efficiency, speed, and structure—you’re working with a Bottom Liner.

No guessing. No assumptions. No missteps.

Then Comes the Hard Part: Adjusting

Here’s the truth most salespeople don’t want to hear. Sales is not about your comfort. It’s about their comfort.

If you’re a Relator selling to a Bottom Liner, your job is to tighten up. Be prepared. Be early. Be clear. Lead with the bottom line and support it with facts.

If you’re a Bottom Liner selling to a Relator, your job is to slow down. Engage. Ask questions. Listen fully. Build trust before pushing toward decisions.

And yes—sometimes that means doing what doesn’t feel natural.

Because comfort closes deals. Not yours—theirs.

Teachable Takeaways You Can Use Immediately

If you want to apply this today, here’s where to start:

1. Identify your default style. How you buy is usually how you sell.

2. Stop assuming similarity. People who think like you are the exception, not the rule.

3. Ask the diagnostic question early. It saves time, money, and frustration.

4. Match energy, pace, and priorities. Not personalities—communication styles.

5. Practice flexibility. Adaptability is not inauthentic; it’s professional.

When salespeople learn this skill, close rates rise, resistance drops, and conversations feel easier—not because selling gets simpler, but because it gets smarter.

This is one of the core principles I teach in my keynote presentations and leadership trainings, because it applies everywhere—sales, management, customer service, and even personal relationships.

Once you understand how people communicate, you stop pushing and start connecting.

And that’s when real results happen.

If your sales conversations feel harder than they need to be, or great opportunities keep stalling for reasons you can’t quite put your finger on, I can help. In my keynotes and trainings, I teach teams how to recognize communication styles in real time, adapt without losing authenticity, and create conversations that make clients feel understood and confident saying yes. When your people learn how to meet buyers where they are, results follow. I’d love to bring this message to your team. Give me a call!