Sales Training Weekly: Selling Through the Customer’s Eyes — The Art of Asking the Right Questions | 士丹利周

Why are customers uninterested in your pitch? In an age of information transparency, what real value can a salesperson offer? And what kind of questions truly resonate with customers?

Have you ever received a cold call? The script always sounds the same:
“Our company can help you…”
“Our product is on special offer…”
“We have the perfect solution for you…”

These pitches are filled with “we, we, we,” and lack any relevance to the customer’s perspective. Unsurprisingly, most people hang up before the caller even finishes the sentence. This highlights a crucial truth: customers don’t care who you are — they care whether you understand their needs.

The Age of Empowered Buyers

Technology has fundamentally reshaped the world of sales. The internet is now the new showroom. Within minutes, customers can search for the exact product or service they need, compare prices, and make informed decisions — anytime, anywhere. In this era of transparency and choice, the traditional sales approach — simply repeating product specs and pricing — is obsolete.

The value of a modern salesperson is no longer in providing information, but in offering insights that customers cannot find online. These may include strategic perspectives, personalized advice, or even helping the customer uncover needs they weren’t consciously aware of.

It’s Not About What You Say — It’s About What You Ask

Many sales professionals claim they “understand the customer,” but in practice, they often just recite features and repeat benefits, pushing their products without truly listening. And trust me, customers can tell whether you’re genuinely trying to help or just pushing to close a deal.

Let’s look at some examples:

A customer says they need a drill. What they need is a hole of a specific size and depth. Instead of asking which brand or how much they want to spend, a good salesperson should ask: “What material are you drilling into? How deep? What’s the purpose?” That’s the kind of question that leads to real understanding.
A patient says they need a filling from the dentist, but what they truly want is a healthy and beautiful smile.
A client says they want to replace their windows — but the real issue might be leaks, safety for children, or better insulation.
A diner requests a quiet table — but that’s because they’re hosting an important business dinner and need a discreet setting.

In each case, the surface-level request masks a deeper, emotional motivation. And that’s where asking the right questions becomes critical.

A Good Question Is More Powerful Than the Perfect Pitch

The ability to ask the right question is what transforms a sales conversation from a push to a pull — from persuasion to discovery. It gives you access to facts, motivations, and emotional drivers — and ultimately increases the likelihood of a meaningful, successful close.

You’re probably familiar with open-ended and closed-ended questions. But let’s go further and distinguish between fact-finding and emotion-based questioning strategies:

Fact-finding questions focus on data and decision-making processes, e.g., “What’s your budget?” or “Who is the final decision-maker?” While these can be important, they often make clients feel interrogated — even defensive. Most of the time, these questions yield generic or vague responses.
Emotion-based questions, on the other hand, tap into the client’s hopes, challenges, and aspirations. Questions like:
“What are you hoping this change will achieve?”
“How do you think your team will feel about this new approach?”

These questions show genuine interest and inspire trust. They help the customer imagine success, and that emotional engagement is what leads to buying decisions.

The best salespeople never start with products — they start with people. They learn about the customer’s business, industry, trends, and challenges. Then, they identify problems, propose tailored solutions, and guide the customer toward a desired future.

Here are a few powerful examples you can use:

“Is this the outcome you’re looking for?”
“Does this solution meet your expectations?”
“How do you think your employees would respond?”
“Do you believe this investment will improve morale?”

These questions shift the conversation from price and specs to vision and purpose — and that shift is what closes deals.

Avoid the Two Worst Questions in Sales

Let’s be clear — there are two questions you should never ask a customer:

“What would it take to win your business?”
This almost always invites a price war and reduces your value to just a number.
“What keeps you up at night?”
This old-school question is manipulative and insincere. Today’s customers will likely respond with, “That’s none of your business.”

Instead of digging for pain points, focus on discovering the client’s goals, aspirations, and personal definitions of success. Great salespeople create resonance, not resistance. They build trust — not pressure.

Sales is no longer about pitching. It’s about building relationships. When you learn to ask good questions — from the customer’s point of view — you demonstrate empathy, professionalism, and value.

When the client trusts you, they don’t feel sold to. They feel supported. If your offer meets customers’ needs — the deal will be closed naturally.

5/5/2025–11/5/2025