Are You Asking Enough Rapport Building Questions on Your Sales Calls?

Summary:

• Rapport-building questions are a classic sales call technique—but there are certain situations when you don’t want to use them.
• If you have a genuine connection to your prospect already, these questions can be a good way to move the relationship forward. But if you don’t, they can feel hamfisted and make your prospect uncomfortable—as well as wasting their time.
• Your goal is always to connect with your prospect, and rapport-building is only one way to do it. You can also often engage your prospect by speaking directly to their pain points and presenting valuable solutions.
• This more straightforward approach is especially useful if the relationship is new or the prospect’s short on time.
• The right dialing tools can also help you connect authentically with prospects. Use PhoneBurner to dial faster, enjoy higher call quality, avoid being incorrectly labeled as spam, and follow-up efficiently afterwards.

Small talk. Icebreakers. Weekend plans. For decades, rapport-building questions have been a go-to for salespeople trying to “warm up” cold conversations. But is that still the right move?

There’s a growing school of thought, especially in high-velocity B2B environments, that says no—at least, not always. Rapport-building questions can be great ways to move a conversation forward when you have a genuine connection with your prospect—but done poorly, they can come off as fake, waste your prospect’s time, and derail your pitch before it even starts.

PhoneBurner exists to help sales reps have more high quality phone conversations—so in this article, we’ll unpack when rapport-building questions actually help, when they hurt, and how to ask the right ones in a way that builds real trust.

When Building Rapport Helps (& When It Doesn’t)

Rapport isn’t always the shortcut to connection it’s made out to be. Research shows that although top-performing salespeople have longer phone conversations with prospects, they actually talk less than the rest of their teams—and spend more time engaging the clients in meaningful conversations.

But here’s the context that’s missing from that statistic: prospects (especially newer ones) aren’t likely to stick around for long conversations unless the information you’re giving them is valuable. Someone you’ve talked to a few times might be interested in telling you about their weekend plans—but someone who doesn’t know you probably only cares about whether or not you’re offering a solution to their pain point.

That means you can’t just try to make small talk when you want to keep a new prospect on the line. In fact, cutting to the chase can be just as useful, depending on how well you know the person on the other end of the line and what signals you’re getting from them.

There’s no exact science to this, but here are some tips for how to choose the right approach in the moment:

When Rapport-Building Helps

• In discovery calls, where you’ve already earned the right to dig deeper.
• With warm leads or referrals, where some context or mutual familiarity exists.
• To match energy, especially with relational buyers in industries like real estate or insurance.
• As a tool for mirroring empathy—e.g., “I imagine your calendar is packed, so I’ll be quick.”

When Brevity Is Better

• In cold calls, especially early in the call. Prospects want clarity, not chit-chat.
• With task-oriented buyers who prefer to get to the point.
• When it’s clearly scripted or inauthentic—“I see you like golf!” won’t cut it anymore.

Bottom line: rapport should be earned, not forced. In many cases, you want to start by offering value. If you do that, rapport will often follow.

Best Practices for Natural Rapport-Building

In situations where you do want to ask rapport-building questions, here are some tips on how to make them count:

• Lead with relevance. Hook them with a clear reason for your call first.
• Mirror their tone. If they’re chatty, match it. If they’re direct, follow suit.
• Use contextual cues sparingly. Mentioning something from their LinkedIn is fine—but only if it feels genuine.
• Let it happen naturally. Ask how their day is going if it flows—don’t force it as a lead-in.

You can read more about these techniques (and others) in our guide to relationship selling. But keep in mind that this approach to selling is still about solving problems for customers. You’re just taking a longer-term view of the relationship because of the potential value it has.

Examples by Industry

Real Estate

Good: “What’s the number one thing you’re looking for in your next home?”

Risky: “I saw you vacationing in Napa—did you have fun?”

SaaS

Good: “How are you currently managing [pain point]?”

Risky: “Saw your CEO posted about winning an award—big party?”

Insurance

Good: “What coverage gaps are you most concerned about?”

Risky: “I noticed your alma mater won last weekend—did you go?”

Finance

Good: “A lot of people I speak to are increasingly concerned about the market’s impact on their retirement. Is that something you’ve been thinking about?”

Risky: “That’s a great-looking dog in your profile pic—what breed?”

Open vs. Closed Questions: Which Build Better Rapport?

You might have noticed something about the examples above. Not only are the examples of good questions directly related to a perceived need that the prospect has; they’re also open-ended and encourage the prospect to start talking.

By contrast, the “risky” questions are all pretty straightforward yes-or-no queries. The prospect will either give a one-word answer that immediately puts the ball back in your court—or they’ll just lose interest and tap out of the conversation altogether.

Open-ended questions prompt more natural dialogue and show interest in the prospect’s needs. Here are some other useful examples you can use:

• “What are you hoping to accomplish this quarter?”
• “What’s been most frustrating about your current setup?”

Closed-ended questions can feel like an interrogation if overused—but they can be great for quick clarity when you use them correctly. Here are a few that can work in the right situations:

• “Is that something you’re handling internally?”
• “Do you already use a tool for that?”
• “Does your [product/service] give you a way to [known gap among existing solutions]?”

In both of these examples, you’ll learn something valuable from the answer even though it’ll likely be short. And if you’ve planned for both answers, you can gain momentum to move you into the next part of your pitch.

To Sum Up: Start with open-ended questions to build connections. Use closed-ended ones to confirm or clarify.

Related: 7 Common Conversation Mistakes You Need to Avoid in Sales

Use PhoneBurner to Track & Refine Your Relationships with Prospects

Every phone sales rep takes notes about their calls—at least, they should. But using PhoneBurner’s dialing platform gives you extra features to help improve rapport and build genuine relationships with prospects.

Here’s how:

• Start every conversation naturally with delay-free connections—no off-putting “telemarketer beep” that raises skepticism instead of rapport.
• Use call transcripts and AI summaries so reps can focus more on active listening and less on manual note-taking. Reviewing transcripts can help you see how rapport-building moments play out, or when other tactics are more effective.
• Use custom disposition buttons to trigger the correct follow-up for every call outcome, saving you time and leaving less to chance.
• Get notified when prospects open emails, click links, view docs, or watch videos so you know exactly who is engaged and what they’re interested in. PhoneBurner’s SmartSender feature helps you keep reach-outs focused instead of relying on small talk.

Our power dialer also lets you reach up to 4x as many prospects in a given period, and helps reduce spam flag risks for your legitimate business calls. When used right, PhoneBurner helps your team continuously improve how they connect—not just what they pitch.

Stop Trying to Build Rapport Out of Thin Air—& Start Earning It Naturally

Rapport-building questions aren’t dead—but they’re not a free pass to “get in the door,” either. In a world where attention spans are short and trust is earned in seconds, the best reps lead with clarity, insight, and respect for their prospects’ time.

And remember: rapport isn’t an end in itself; it’s a means to one. And there are other roads you can take. If your questions invite conversation, demonstrate understanding, and move the call forward, you’re doing it right—even if you never ask about someone’s weekend.

PhoneBurner can make those conversations easier to track, review, and improve over time. Start your free trial here if you’re not a user already, and see it in action for yourself.