Stop Pitching, Start Exploring: 5 Questions That Build Real Connection in Sales

Too many salespeople lead with their pitch.

They come prepared with the features, the case studies, the numbers—ready to present. But they miss the most important part: the person on the other side of the conversation.

Real sales momentum doesn’t come from speaking, it comes from listening.

And listening starts with asking the right questions.

In this blog, we’re sharing five open-ended, connection-building questions that help you move from awkward small talk to real insight. These prompts are rooted in the BeUseful™ approach from our course Conversations Made Easy and reinforced by the trust-building strategies in our book The Client Retention Matrix.

Why Connection Beats Persuasion

People don’t want to be sold. They want to feel seen.

When you approach a sales conversation with curiosity instead of pressure, you signal respect, presence, and professionalism. That’s what creates trust, and trust closes deals.

In Conversations Made Easy, Chris teaches that the best conversations are built around being useful, staying present, and staying curious. These five questions do exactly that.

5 Questions That Change the Conversation

Use one or more of these in your next discovery call, proposal meeting, or even in a LinkedIn message. Each one is designed to open up the conversation and uncover what really matters.

1.

“What’s been tried before—and what didn’t work?”

This question uncovers past frustrations, failed solutions, and key lessons.

It tells you not only what to avoid, but how to position your offer differently.

From The Client Retention Matrix: Clients stay longer when they feel like you understand their full history—not just their current problem.

2.

“If we were talking 6 months from now and everything had gone right, what would be different?”

This forward-focused question helps them define success in their own words.

It also gives you a clear picture of what they care about most.

Bonus: Use their answer to tailor your offer and reinforce the right outcomes.

3.

“Who else cares about solving this—and why?”

This question uncovers internal decision-makers, influencers, and urgency drivers.

You’ll know who’s involved, what’s at stake, and what narratives are shaping the decision.

This reduces surprise objections later and gives you more insight into how to follow up.

4.

“What would make this feel like a great conversation, even if we didn’t move forward?”

This is a trust accelerator. It shows you’re not just there to win the deal—you’re there to serve.

It immediately lowers defenses and invites honesty. You’ll get real answers and stronger rapport.

5.

“What do you wish someone in my position would ask—but usually doesn’t?”

This is your differentiator. It positions you as thoughtful, present, and unlike anyone they’ve spoken to before.

From Conversations Made Easy: The goal is not just to say the right thing—it’s to create the space for the right thing to emerge.

Build Trust First. The Sale Follows.

When you lead with questions like these, you stand out in a noisy space.

You shift from pitching to exploring, and from selling to solving.

The result?

• Deeper conversations

• Shorter sales cycles

• More loyal, aligned clients

This isn’t just good conversation, it’s good business.

Ready to Learn the Full System?

Inside our course Conversations Made Easy, you’ll learn:

• The full BeUseful™ framework for high-impact communication

• How to structure conversations that convert

• The right questions to ask—and when to ask them

• Templates, scripts, and real-world prompts to guide every call

Enroll in Conversations Made Easy Today

For custom training, speaking, or white-labeled content partnerships, explore options at ChrisJenningsGroup.com.