The best salespeople don’t sell—they ask the right questions

Most salespeople talk too much. The best ones? They ask the right questions.

A friend of mine asks a lot of questions when he meets someone—so many that it can feel uncomfortable—almost intrusive.

When I called him out on it, he simply said:
"If I don’t ask questions, how else am I going to learn about this person?"

That stuck with me.

In sales, questions are everything. The best salespeople don’t just pitch—they ask the right questions to uncover real motivations. But there’s a fine line between interrogating and guiding a conversation.

Recently, I worked with buyers relocating from California. Their job required them to move by a set date—but they didn’t want to leave before their daughter’s graduation.

I wouldn't have uncovered the actual pressure points if I had just accepted their timeline at face value.

So I asked:

• Can you move earlier? If so, what happens?

• Can you carry both properties? If so, what happens?

• What’s the worst-case scenario? What’s the ideal?

• What flexibility do you have, and how long will your job wait?

• Then what happens? Then what happens?

These "what ifs" weren’t just about gathering information—they helped my clients process their own decisions.

This works across every industry.

In medical sales, a doctor once told me flat-out he wasn’t interested in switching tests. Instead of pushing, I asked:
"Really? You wouldn’t want anything to change to your current service?"

That one question opened the floodgates. He vented about turnaround times, accuracy issues, and a lack of rep support.

A few weeks later, he decided to try our test. Not because I sold him—but because I helped him realize his pain points.

Great salespeople don’t interrogate. They guide.

Most salespeople think their job is to persuade. The best know their job is to uncover the truth.

Whether it’s helping a doctor rethink their options or guiding a buyer through a major life decision.

Trust isn’t just built by making things easy—it’s built by asking the right questions and truly understanding your client’s world.