Want to Close Deals Faster? Start With This Question

You’re in a sales conversation. The prospect seems interested, the vibe is good—and then, somehow, it stalls.

They go cold. Or ghost you. Or give a polite, “Let me think about it.”

This happens all the time. And often, the root cause isn’t your pitch, it’s your questions.

More specifically, it’s the questions you didn’t ask.

One of the most powerful tools in your sales toolkit isn’t a script or a strategy, it’s this simple question:

“What made you start looking now?” 

This one line, when asked sincerely, can shift the entire tone of a conversation. It moves you from surface-level dialogue to real insight, and from another vendor to a trusted guide.

Let’s explore why it works, how it fits into the frameworks from our books and courses Conversations Made Easy and The Client Retention Matrix, and how to use it effectively in your next call.

Why This Question Works

People don’t buy based on specs. They buy because something has changed. Something triggered the search.

Maybe it’s internal pressure. A frustrating experience. A new priority.

When you ask, “What made you start looking now?”, you give them permission to open up and tell you what’s really driving the decision.

That information gives you leverage. Not to manipulate, but to connect.

You learn what matters. You learn where the urgency is. You learn how to help.

In Conversations Made Easy, Chris teaches that great conversations aren’t about perfect pitches. They’re about genuine curiosity and intentional questions that uncover meaning.

This is one of those questions.

Where It Fits in the Sales Conversation

This isn’t a qualifying question. It’s a relationship-building one.

Here’s when to ask it:

• Early in the discovery call, once basic context is established

• After they share a challenge, frustration, or vague reason for reaching out

• When you sense they’ve tried other options, but are still looking

Here’s what it might sound like:

“Out of curiosity, what made you start exploring this now?”

“What changed recently that pushed this to the top of your list?”

Keep your tone calm and conversational. Then pause. Let them fill the space.

The Retention Tie-In: Trust Starts Before the Sale

In The Client Retention Matrix, one of the key retention drivers is emotional alignment—the prospect needs to feel understood before they ever buy.

Asking meaningful questions like this one shows:

• You care about their timing and context

• You’re not rushing to pitch

• You’re here to listen and tailor the experience

This builds pre-sale trust, which carries into the client relationship and increases retention and referral potential down the line.

What to Do With the Answer

When they respond, listen for:

• The emotional trigger (“We’re overwhelmed.” “Something broke.” “Our last provider let us down.”)

• The urgency or timeline

• Any frustration with past attempts

Now you’re equipped to personalize your response.

Not just “Here’s what we offer,” but:

“Since you’re dealing with [their issue], here’s how we’ve helped others in similar situations.”

You’re not selling—you’re solving.

That’s what separates average sellers from top performers.

The Bottom Line

In a world full of salespeople pushing solutions, the one who takes time to explore the why now earns trust faster—and closes deals with less resistance.

It’s not about clever tactics. It’s about conversational leadership.

That’s the heart of Conversations Made Easy—a framework designed to help you shift from pitching to partnering, from reacting to guiding, and from awkward sales calls to real momentum.

Want More High-Impact Questions That Close Deals Faster?

Inside Conversations Made Easy, you’ll learn:

• The complete BeUseful™ approach to building trust through conversation

• The question structure that turns resistance into clarity

• Real-world scripts and prompts that move deals forward without pressure

• How to confidently lead conversations that convert—without feeling pushy

Enroll in Conversations Made Easy Today

For group training, licensing, or deeper retention strategy, visit ChrisJenningsGroup.com.