Stop Trying to Be Interesting and Start Being Interested

Early in my sales career, I thought being good at sales meant having the answers. Know your company, understand your differentiators and your competition, and be prepared to explain why someone should work with you. Then, when you finally get a prospect on the phone or earn a meeting, make sure they understand everything you can do for them.

There’s nothing necessarily wrong with any of that. But over time, I learned that knowing what to say isn’t nearly as important as knowing what to ask.

Some of the best sales conversations I’ve ever had weren’t the ones where I said something brilliant. They were the ones where I became genuinely curious about the person sitting across from me.

• What are they trying to accomplish?

• What’s getting in the way?

• Why does that matter?

• What happens if nothing changes?

That sounds simple, but I think it’s one of the hardest disciplines in sales. We spend so much time preparing to talk we sometimes forget to prepare to listen. We practice our value proposition, prepare presentations, learn how to handle objections, and make sure we can articulate what makes us different. All of those things matter, but most of that preparation is focused on what we are going to say.

Listening requires a different kind of preparation. You may go into a conversation with questions you want to ask, but you also have to be willing to abandon those questions based on what you hear. Sometimes the best question isn’t the one written on your meeting plan. It’s the follow-up that comes naturally from something the client said 30 seconds ago.

Think about the last sales meeting you had. When the prospect was answering one of your questions, were you really listening to their answer, or were you already thinking about what you wanted to ask next? Were you listening for something worth exploring, or waiting for an opening to talk about your solution?

I’ve certainly been guilty of the latter. There have been plenty of times in my career when a prospect said something that should have caused me to stop and dig deeper. Instead, I recognized a familiar problem and immediately went into solution mode: “We can help with that.”

Maybe we could. But I hadn’t earned the right to know that yet.

A fundamental skill we teach at Butler Street is understanding the client’s operating reality, and I think it’s where genuine curiosity becomes so powerful.

If a client tells you they’re struggling to fill positions, that’s useful information, but it isn’t necessarily the problem.

• Why are they struggling?

• How long has it been happening?

• What has changed?

• What have they already tried?

Once you understand the situation, you can begin exploring the impact. If those positions are staying open longer, for example, how is that affecting the team’s ability to hit production goals?

Now you’re having a very different conversation.

You’re no longer simply talking about open positions; you’re talking about what those open positions mean to the business.

That’s the difference between collecting information and truly understanding a problem.

And I think this matters even more today. Buyers have access to more information than ever before. They can research your company, your competitors, and your services before ever speaking with you. With AI, they can get answers in seconds to questions that once required a conversation with a salesperson.

That changes the value we need to bring.

If everything a salesperson plans to tell a prospect can already be found on a website or generated with an AI tool, why does the buyer need the salesperson?

I don’t think the answer is more information.

The value comes from helping buyers make sense of the information they already have. Maybe that means asking a question they haven’t considered, connecting something they said earlier to a larger business issue, or helping them think through the impact of maintaining the status quo.

They don’t need another person to walk in and read through a capabilities presentation. They need someone willing to understand their business well enough to help them think differently about a problem.

That starts with curiosity.

It means listening for the answer behind the answer, asking one more question when it would be easier to move on, and resisting the urge to immediately connect everything you hear back to your solution. Sometimes it also means being comfortable enough to admit you don’t know something and simply asking the client to help you understand.

The best salespeople I’ve worked with know their business. They understand their solutions, their competition, and the value they can provide. But that knowledge alone isn’t what makes them great sellers. What separates them is how genuinely interested they are in the person sitting across from them.

They want to understand their clients’ businesses and how decisions get made. They’re curious about what changed, why it changed, and what happens if nothing changes. And because they approach conversations that way, they tend to uncover things other sellers miss.

So, before your next client conversation, don’t just ask yourself, “What do I want them to know?”

Ask yourself,

“What do I want to understand?”

Because the best sales conversations aren’t built around how interesting you are.

They’re built around how interested you are.

If you’re looking to help your sales team have better conversations, ask better questions, and create more value in every client interaction, Butler Street can help. Contact us to learn more about how we work with sales teams to build the skills, confidence, and habits that lead to stronger conversations and better results.

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Frequently Asked Questions About Better Sales Conversations

Why is curiosity important in sales? Curiosity helps salespeople move beyond surface-level information to understand the client’s goals, challenges, priorities, and the business impact behind them.

What makes a good sales question? Good questions uncover what is happening, why it matters, what has changed, and what happens if nothing changes. Strong follow-up questions often come from listening carefully rather than thinking of the next question you have planned.

How is AI changing the salesperson’s role? Because buyers can access information more easily, salespeople create more value by helping clients interpret what they know, think through business issues, and make better decisions—not simply by providing more information.