11 Real Rapport-Building Questions That Actually Work in B2B Sales Calls

We Almost Lost the Deal Until We Asked This One Question

How Building Rapport in Sales Isn’t About Selling — It’s About Seeing People

I remember the deal clearly.

It was a Wednesday, mid-quarter. Our team had been chasing this one client — a fast-scaling tech startup — for over a month. We’d done all the prep: sent the decks, followed up, positioned the product perfectly. On paper, they were a perfect fit.

And yet, the call felt… off.

The decision-maker was polite, but distant. We walked through the value props, dropped in a case study, even offered a generous pilot. Still, something was missing.

And then my colleague did something unexpected.

He leaned back, paused, and asked:

“Hey, just out of curiosity — what’s going on that made this conversation important right now?”

Silence.

Then the CTO exhaled, and said:

“Honestly? Our last sales tool just crashed during a board presentation. Our CRO was furious. I need to fix this fast — but we’ve been burned before, and I’m sick of hearing pitches.”

Boom. There it was. The emotion, the urgency, the human behind the process.

That single moment shifted everything. We stopped pitching and started listening.

And two weeks later, the contract was signed.

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🤝 Why Rapport Isn’t a “Tactic” — It’s the Entire Game

Sales is emotional. Your prospects are human beings — with stress, goals, anxieties, and internal politics.

Rapport isn’t built on mirroring body language or tossing out forced compliments. It’s built when the other person feels safe, understood, and seen.

That’s when you stop being a salesperson — and start being a trusted guide.

🧠 So How Do You Actually Build Real Rapport?

Successful selling is all about asking the right questions. But building good connections with your prospects is just as essential as finding out more about their company, needs, and pain points.

In addition, these types of questions must be genuine to build real trust. When it comes to B2B sales, more than 90% of companies report that they only buy from companies they trust. This puts a lot of pressure on the salesperson, as another survey shows that only 18% of buyers say they trust and respect salespeople.

Try including some of these top rapport-building questions in your next sales call to make your sales efforts even more effective.

🔑 Part 1: 6 Human Ways to Build Rapport in Sales (Without Feeling Salesy)

1. Do Your Homework — But Not Just on the Company

Look beyond their title. Find the person. Where did they go to school? Did they write any content recently? What do they care about outside work? Use that to open the door to an actual conversation — not a pitch.

💬 “Hey, I saw you did your MBA at Georgetown — a close friend of mine was in that same cohort. Small world!”

People light up when you see them beyond their job.

2. Give Real Compliments (That Can’t Be Copied & Pasted)

Don’t say “Congrats on your promotion.” Be specific. Make it clear you actually read or watched something and got something out of it.

💬 “That post you shared about hiring in hypergrowth? I shared it with two of our SDR leads — it hit home. Especially the part about hiring for curiosity.”

That’s a compliment that adds value and starts a conversation.

3. Ask for a Small Yes — Fast

Prospects have their guards up. A simple, low-stakes yes early on can melt resistance.

💬 “Would it be okay if I asked a few quick questions to understand if this is even relevant?”

The moment they say “Sure,” you’ve shifted the dynamic. Now they’re in the conversation with you.

4. Share a Story — Not Just Stats

Stories build emotional memory. You’re not selling features — you’re selling outcomes. So paint a picture.

💬 “We worked with a company in your space that was drowning in manual pipeline reporting. Their VP told us it felt like ‘death by spreadsheet’ every Monday. We set them up with an automated dashboard in two weeks — and she said it gave her her Sundays back.”

That sticks. Data alone doesn’t.

5. Talk Like a Person (Not a Pitch Deck)

Drop the jargon. Cut the script. Use your voice.

💬 “Honestly? I’m not sure if we’re the right fit yet. But if you’re open to it, I’d love to hear what’s on your plate right now and see if there’s any overlap.”

Genuine curiosity beats polished persuasion.

6. Add Real Value — Even If You Never Close the Deal

Want to build instant trust? Help them with something before asking for anything.

💬 “Quick heads up — I saw you’re using XYZ for outbound. A few of our clients had deliverability issues there. If you want, I can send over a checklist that helped them clean it up.”

They’ll remember that — even if they don’t buy today.

Part 2: 11 Rapport-Building Questions That Actually Work (And Why They Work)

Each of these questions is carefully designed to create emotional safety, build trust, and spark honest dialogue. Let’s break down not just what to ask, but why it’s effective and when to use it.

1. “What brings us here today?”

Why it works:

This is one of the simplest and most open-ended ways to begin a discovery call. It avoids jumping straight into a pitch and instead puts the ball in their court.

Psychological trigger:

It subtly signals that you’re here to listen, not sell. It gives your prospect the power to direct the conversation based on what matters most to them.

Pro tip:

Listen not just for their answer — but how they answer. Tone, speed, and emotion will give you clues about what’s really going on.

2. “Can you walk me through what’s going on from your perspective?”

Why it works:

This creates space for them to tell their version of the story. It acknowledges that there may be multiple views internally and makes them feel like their opinion matters.

Psychological trigger:

You’re validating their role as a key decision-maker. People love to feel understood — and this question invites them to paint the full picture.

Pro tip:

Use reflective listening here. Repeat key parts of what they said with empathy. E.g., “So it sounds like things got a little chaotic after the last rollout?”

3. “What’s been the most frustrating part about this process?”

Why it works:

This is where rapport deepens. Frustration is an emotional word — and when you can surface someone’s pain honestly, trust grows.

Psychological trigger:

Naming pain creates connection. It also positions you to be the solution to a real problem — not a generic pitch.

Pro tip:

Don’t interrupt. Let silence do the work. Some of the best responses come after a pause.

4. “How’s this issue affecting the rest of the team?”

Why it works:

It expands the scope from an individual issue to an organizational impact. This question shows you care about their world — not just their wallet.

Psychological trigger:

People are social. They want to help their team. When they articulate how others are being impacted, it heightens urgency and emotional buy-in.

Pro tip:

Look for language like “we’re all feeling…” or “my team’s overloaded…” — those are emotional buying signals.

5. “Have you tried anything else to solve this?”

Why it works:

It shows that you respect their intelligence and don’t assume you’re their first option. It also uncovers failed attempts you can learn from.

Psychological trigger:

Buyers want to be heard, not lectured. This question gives you vital insight into their journey and makes you part of the solution, not another pitch.

Pro tip:

Be curious, not critical. “That’s interesting — what didn’t work about that approach?” opens the door to deeper conversation.

6. “What would a win look like for you personally?”

Why it works:

This flips the conversation from company-level to personal outcomes. People don’t just buy for business reasons — they buy to feel successful, safe, and smart.

Psychological trigger:

Personal stakes increase emotional engagement. If helping you looks good for their reputation, career, or stress levels — they’ll be more invested.

Pro tip:

Tie your value to their goals. “So if we can get you out of those fire drills by end of quarter, that’s a win?”

7. “If nothing changes, what happens next quarter?”

Why it works:

This gently introduces urgency without fear tactics. It moves the conversation from the present to the near future — making inaction feel risky.

Psychological trigger:

The brain avoids pain more than it seeks gain. When they describe the cost of doing nothing, you don’t have to convince them — they’ll convince themselves.

Pro tip:

Follow up with, “How would that impact your team / KPIs / bandwidth?” to anchor the consequences.

8. “What’s made you skeptical about solutions like this?”

Why it works:

This disarms objections before they surface. It shows confidence and empathy. You’re not afraid of skepticism — you’re inviting it.

Psychological trigger:

You’re lowering resistance. When prospects feel safe to express doubts, they become more open to exploring new outcomes.

Pro tip:

Listen without defending. Instead say, “Totally fair — I’ve heard that from others. What would help shift that for you?”

9. “Who else should we be thinking about as we explore this?”

Why it works:

You’re showing foresight and respect for internal processes. It signals that you’re collaborative — not trying to go around anyone.

Psychological trigger:

You build trust by respecting their buying ecosystem. You also gain insight into power dynamics and potential champions or blockers.

Pro tip:

Ask this before you pitch. Early buy-in across stakeholders = smoother path to close.

10. “What kind of support would make this a no-brainer?”

Why it works:

You’re not asking “Will you buy?” — you’re asking, “How can I make this easy for you?” That’s a game-changer.

Psychological trigger:

You’re positioning yourself as an enabler — not a closer. This builds trust, and helps them shape the offer themselves.

Pro tip:

Use their words in your proposal. When they see their own language reflected back, conversion rates skyrocket.

11. “What’s the best way I can help you — even if we don’t end up working together?”

Why it works:

This is a relationship-building move. It shows that your value isn’t conditional. You’re in it to serve, not just sell.

Psychological trigger:

People remember generosity. And ironically, when you remove pressure — your close rate goes up.

Pro tip:

Have a few free tools, templates, or intros ready. Give before you ask.

🔚 Final Thought: Build Trust Like You’d Build a Friendship

You don’t walk into a party and ask someone if they want to commit to a five-figure purchase.

You ask about them. You connect. You find a reason to keep talking.

Sales is no different.

The best rapport-building questions don’t feel like a sales script. They feel like curiosity. Like care. Like real connection.

And when you lead with that? Sales follow.

Want to Empower Your Sales Team to Build More Human, High-Trust Conversations?

This blog shows how the right questions spark real connections.

Prolumios takes it further — we record and summarize your sales calls so you can:

✅ Spot what’s working

✅ Improve every rep’s rapport-building skills

✅ Close deals through trust, not pressure

👉 Try Prolumios — and turn every sales call into a relationship that converts.