Getting Customers to Open Up: How to Uncover What They’re Not Telling You

In sales, few things are more frustrating than knowing your prospect isn’t telling you the whole story. You can sense something’s holding them back — but every question feels like hitting a wall.

This week’s episode dives into one of the hardest but most powerful skills in sales: learning how to get customers to open up.

Every customer has a story—but not all of them will tell it. Can you ask the right questions to uncover what they’re really thinking?

I recorded a podcast on this topic this week! Here's a breakdown of my insights.

Listen to Podcast on Spotify

Why Customers Hold Back

When prospects avoid giving details, it usually comes down to fear — fear of being sold to, fear of losing leverage, or fear of wasting time. They want to know: Do you really care about helping me, or just about closing the deal?

As salespeople, we often make the mistake of talking too much and listening too little. The best thing you can do is slow down and make your prospect feel safe. Listen more than you speak. Match their energy. And show genuine curiosity — not pressure.

The Power of Genuine Listening

You’ve heard it before: two ears, one mouth. Use them in that ratio.

Salespeople often think the customer does most of the talking… until they listen back to a recording and realise they dominated the conversation. Listening builds trust faster than any sales pitch ever could.

Try sounding slightly uncertain — “So, if I understand you correctly…” — and let the customer fill in the blanks. People naturally want to help clarify, and that opens the door to deeper conversation.

Three Questions That Unlock Truth

If you’re struggling to get prospects to open up, start here:

1. “What’s most important to you when it comes to [X]?”

   • This moves the conversation toward what really matters.

2. “What are your top two or three biggest frustrations?”

   • People love talking about pain points. Ask and listen.

3. “What are you most concerned or skeptical about moving forward?”

   • This reveals hidden objections before they block the sale.

Silence Speaks Volumes

Don’t rush to fill every pause. Silence can show confidence and give your customer time to think. If it drags on, simply ask:“What are you thinking?” Then stay quiet.

This one question can uncover fears, objections, or unspoken thoughts that would otherwise kill the deal.

From Interrogation to Investigation

There’s a fine line between questioning and grilling. If your conversation feels like a police interview — “Do you? Would you? Can you?” — the customer shuts down.

Instead, switch to open-ended, curiosity-driven questions: “How do you usually handle this?”, “When was the last time that happened?”

Move from interrogation to investigation. It’s not about checking boxes — it’s about discovery.

When Customers Stay Vague

Sometimes, vague answers happen because they don’t know what they need. Other times, they’re protecting themselves or holding back for negotiation.

Here’s your move:

• Use “So, so, so…” to gently prompt for more information.

• Ask, “Help me understand…” to clarify.

• Offer a completely wrong guess — they’ll correct you fast and reveal the truth.

The goal isn’t to corner them; it’s to help them clarify what they actually want.

The Analogy Effect

If a client gets stuck on details — like price — step back and use an analogy. For example:

“Have you ever bought cheap shoes that fell apart after two months? You end up wishing you’d spent a little more for quality.”

Analogies take the pressure off specifics and help people see the value in what you offer.

If you’d like to dive deeper, follow me on LinkedIn or subscribe to the podcast on Spotify.

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