How to Get Prospects to Open Up with 3 questions

The time has come.

You’ve been chasing this account for months.
You finally got the meeting and you showed up right on time.
You’ve memorized every technical spec, and you’ve role played the toughest objections with your team until the answers roll off your tongue. Nothing can go wrong now.

And now you’re sitting there. In their office. Face to face.

So… what now?

You’ve read a dozen books. You’ve now taken the company sales training for a while. You follow the best YouTube channels.
All you need to do is start the conversation and earn their trust.

But what do you say?

After almost 30 years in sales, I’ve learned this: 80% of your chances to win or lose a sale are decided before you ask your final question. Yes, you read that right. The game is won or lost in the first few minutes.

Because when you sit across from a new client, you’re up against an invisible but very real barrier: natural distrust. That little voice in their head going, "What’s this person going to try to sell me?"

It’s instinctive. It’s human. It happens to all of us, especially when someone enters our territory. And if you don’t handle that first moment well, the rest of the meeting will be uphill. Every question will sound like a trap. Every offer will be met with suspicion.

And no course, no book, gives you real advice on how to get your prospect to open up, to relax and start creating rapport.

So here’s my simple advice: Forget about selling for the first 4 to 10 minutes of the meeting. Don’t pitch. Don’t push. Don’t even think about your product.

Use that time to break the ice in an authentic way. Help the other person lower their guard. Help them start to see you as a trustworthy human being, not just another salesperson rushing to close.

How do you do that?
With three specific questions that get anyone to open up. They’re disarming. They’re genuine. And they work.

Nobody feels attacked when you ask these. In fact, they usually enjoy answering. Why? Because these questions invite them to talk about their favorite topic: themselves.

Here they are:

1. “How did you get into this role?”

Most people like talking about themselves. It’s just human nature.

This question gives them a chance to tell their story, their career journey, their milestones. And you? You just listen. Don’t interrupt. Don’t take notes. Not yet. Don’t plan your next move or what to say next. Just listen. Genuinely listen until it hurts.

This is a moment to build a real connection. Because being genuinely heard? That’s rare and powerful.

This is one of the few moments I recommend setting the pen down. Look them in the eye. Be present. Just look them in the eye, nod. It's more than hearing, more than listening. You must understand your client.

2. “What do you enjoy most about your job?”

It doesn’t matter if you’re talking to a CEO or a plant manager, this question works. It shows you care, and it gives you insight into what drives them.

That can be pure gold later, when you tailor your pitch to what really matters to them.

Years ago, I asked this to a head of production. He paused, looked me dead in the eye, and said: "Not a thing."

I thought he was joking. He wasn’t. A few days later, I followed up and learned he had just quit.

Rare and funny anecdote, sure. But that simple question can uncover big things.

3. “Why do your customers choose your company?”

Trick of the trade: This one’s a gem. First, it gets them talking positively about their business. Second, it gives you ammunition for when price objections pop up.

Because most companies aren’t proud of being the cheapest (unless you're Walmart or Dollar General). They usually talk about quality, service, innovation, or trust.

So if later someone says, "We need the lowest price," you can say: "Your own customers don’t choose you for that. Why should you expect that from your suppliers?"

Even better, this question doesn’t trigger their defense mechanisms. You’re not selling: you’re making them reflect on their value. You’re learning how to align your offer with what makes them special.

So here’s the bottom line:

If you want smoother, more productive sales meetings, stop selling during those first minutes. Use these three questions, really listen, and build trust.

When the time comes to talk about your product, you’ll be standing on solid ground.

And one more thing: don’t fake it. Don’t pretend to listen. Actually listen. Care.

People can tell when you’re just waiting for your turn to talk. But they also know when someone is truly paying attention. And that’s rare. And valuable.

The best salespeople don’t talk their way into a deal—they listen their way in.

Got your own go-to question for breaking the ice? Drop it in the comments or share this with a friend or teammate who’s just starting out in sales.

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