11 Rapport-Building Questions to Ask in Your Next Sales Call

Sujan Patel is the founder of Mailshake, a sales engagement software used by 38,000 sales and marketing professionals. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.
  • January 19, 2024

Have you ever received a sales call where the salesperson started off with an ultra-casual “How’s it going?” Rapport-building questions like this one can help you establish a relationship.

But something as basic as “How’s it going?” has been overused to the point that it sounds scripted and is immediately recognizable as a sales call.

And the fact is, being pleasant but predictable does little to build genuine rapport with your prospects. Since you have such a short window of time to make a connection with them, why waste it on empty filler when you could be saying something much more effective?

Studies show it takes an average of eight calls to get someone on the phone, so don’t torch all that hard work by asking something shallow like “How was your weekend?”

Instead, make it memorable so that they’ll not only want to talk with you, but also remember you well after the call.

The Benefits of Building Rapport with Prospects

In the high-pressure world of sales, it may seem like taking the time to foster a relationship is a luxury you can’t afford, and that every contact with a prospect should be seen as an opportunity to close the deal as quickly as possible.

But that’s just not how sales works anymore. Buyers need to know that they can trust sales reps – that their needs are being understood, and that the rep they’re speaking to has the knowledge and expertise to recommend a solution to their problems.

It’s all but impossible to achieve this without first taking the time to build rapport with your prospect. That’s because investing in rapport:

  • Lets prospects know you’re listening to their needs
  • Allows you to ask difficult questions that could otherwise scare a prospect away
  • Puts the prospect at ease, enabling the conversation to flow more smoothly

Good Rapport-Building Questions

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.

Questions that build good rapport go beyond the surface level. They’re highly personalized, and not something that just anyone could answer (i.e. “How was your visit to the lake this weekend?” vs “How was your weekend?”). You still need to be professional, of course, but adding a personal element to show you’ve been paying attention will take you a lot further.

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.

1. “What Do You Hope to Accomplish?”

Open-ended questions like this tell prospective customers that you’ll take an active approach to learn about the challenges they’re facing, and make it a priority to solve their business problems. Sales calls should go beyond asking them who they are and what they do. When you ask clarifying and reflective questions, it opens up a floodgate of emotions for prospects. It shows them that you are genuinely interested in their situation and will offer solutions that help them accomplish their goals.

Why It’s Effective: While it’s a simple question, it has the power to build trust and close a sale, especially if the prospect sees your authenticity and genuineness to help. Questions like this make them reflect before they answer. It allows them to clarify the topic to decipher the angle you’re looking for, and proffer honest responses in return. 

2. “Where Were You Before You Started at [Current Company]?”

Open-ended questions are rocket fuel for sales conversations. You should listen more than you talk, so going beyond the basic ‘yes’ or ‘no’ questions gives your prospects a chance to share with you.

Career-related questions give you more insight into their role in the company and their previous experiences. For example, if you’re talking to someone who worked for another company you work with, you could use that to build your own credibility. Also look to see if you have any mutual connections, such as a friend who worked at their old company.

Or, you might discover that the marketing director you’re talking to just got promoted to the position and hasn’t personally experienced many of the challenges a marketing director will face. In this case, part of your sales strategy could focus on how you can help them make a strong first impression in their new role.

Why It’s Effective: Career-related questions are highly personalized and shift the conversation toward your prospect. And most people love to talk about themselves. Psychological studies show it makes us feel good and lights up the same part of the brain that activates when we eat good food or do other self-gratifying activities.

Additional Career-related Questions:

  • “I see you used to work in [other industry]. What made you make the transition?”
  • “You used to work at [former company]? I had a friend who worked there. Do you happen to know [friend’s name]?”
  • “A lot of my clients in [prospect’s role] have told me [specific detail about the job]. What’s your experience with this been like?”

3. “I Noticed You Went to X College. That’s a Great School. What Did You Like Best About It?

Choosing a college isn’t a decision to take lightly, and getting into the school of your choice can be even harder. Most people are proud of where they went to school (and the degree they earned), and they’ll be happy you took notice.

You can usually find this information on Facebook or LinkedIn. It just takes a quick search, and you’ll feel better prepared for your call as a result. Take it a step further by looking up additional details about their school so you’ll have more talking points when you call.

Or, if you can’t find out where they went to college, it’s 100% okay to ask them during conversation. Make a note so you’ll remember it for your next call.

Why It’s Effective: These questions tap into the same psychology of how people love to talk about themselves. It gives them a chance to share a personal piece of their lives and gives you another way to connect with them.

Additional School-Related Questions:

  • “Oh, I know someone who went to [name of college]. Do you happen to know [name of the person]?”
  • “What was your experience at [name of college] like?”
  • “What were you involved in while you were at [name of college]? Any sports, clubs, etc.?”

4. “I Read Your Blog Post on ___. What Do You Think About ____?”

If you think flattery is always insincere and will get you nowhere, you probably aren’t doing it right. Most people can spot meaningless compliments and feigned interest a mile away, which is why any praise or accolades should come without a hidden agenda.

As Dale Carnegie wrote in his quintessential book How to Win Friends and Influence People, being sincere to others, no matter the situation, is critical to building good relationships.

For example, if you mention reading something that your prospect posted on LinkedIn or on their blog and ask for their take on a related issue, you should have a genuine interest in their response.

Why It’s Effective: Taking note of the content they create shows you’re paying attention and care about what they’re sharing. Most people are flattered by this. They feel like they’re providing value or being helpful, which could help break down any communication barriers and get them to open up.

Additional Content-related Questions:

  • “I saw you’re a fan of [podcast or show]. Have you ever listened to [related podcast or show]?”
  • “I saw your latest blog post on [topic or event]. What are some other blogs you read regularly?”
  • “Thanks for sharing that [blog post, article, ebook, white paper] on LinkedIn yesterday. What is your take on this?”

5. “Most People Don’t Know I Do XYZ. Tell Me One Thing Most People Don’t Know About You.”

In the words of Theodore Roosevelt, “People don’t care how much you know until they know how much you care.” Asking “Yes” or “No” questions won’t help your prospect warm up to you. “Tell me about yourself” questions like this ease both you and the prospect into the call.

Your goal should be to have a heartfelt conversation with them, and not sound like they have an appointment with the Feds. Open-ended questions about off-work activities give a personal touch and give insight into what matters to your buyer. Plus, you get to learn about their likes and dislikes, kids, hobbies, passion, and values and beliefs. You could even discover that you have shared experiences—maybe you both like rock climbing, love the same movies or music, or have both visited the Taj Mahal and loved its architecture.

Why It’s Effective: Similarity is one of the four principles of building rapport. The core of open-ended questions like this opens a two-way communication portal that puts prospects at ease and helps you keep the conversation going to give you needed insights.

6. “Imagine All of Your Problems Were Solved—What Would You Do?”

Hypothetical questions can make your conversations with prospects more interesting when done right. For example, using “Imagine” allows you to qualify your prospect by taking them out of their reality and placing them in a fantasy world where anything is possible (and affordable). It also helps you gauge their stage in the buyer journey and tells you the chances of closing a deal with them, either presently or in the near future.

When asking hypothetical questions, a good rule of thumb is to avoid asking pricing questions. Talking about pricing can be saved for subsequent meetings. The aim of your first call with potential clients should be to build trust and rapport.

Why It’s Effective: Hypothetical questions allow potential customers to dream. Their answers reveal their pain points and allow you to customize your solution to meet their needs. They give you a window of opportunity by telling you that they are not totally satisfied with their current solution. The goal of this question is to find the gap between the customer needs and their current solution, highlight your unique selling opportunity and tap into it.

7. If I had the opportunity to pass through your state/city, what would be your top recommendations?

This is yet another question that will make sure your prospects have a lot to say in return while also making them feel valued (since you’re asking for their advice).

Asking this will also allow you to learn more about the prospect and their home state/city. You’ll get insights into what they like or don’t like and what they prioritize.

Plus, it will enable you to connect with them on a personal level through shared experiences. Maybe they recommend a restaurant that you’ve already tried and you go like, “Oh! I’ve been there and their tacos are amazing!”. See, how rapport-building can get easier with such a simple question?

8. What is the most challenging problem you are dealing with in your business/department right now?

Everybody faces challenges at work or business. Asking this question will help you discover your prospect’s current challenges and allow you to show off your expertise if you can suggest potential solutions.

9. Is there any way I can help you with [insert problem]?

What would be your reaction if someone asked you this? You’d probably feel pretty great that they are interested in what you have to say and want to help.

By asking this, you’re not only showing them that you understand their current problems but also that you are willing to provide assistance in whatever way possible.

However, it’s very important that you come off as someone genuinely trying to help. Don’t make this question sound like you’re trying to sell something as doing so will only make you sound pushy — a turn off for your prospects.

10. What’s the top piece of advice you’d give to your younger self?

Encouraging your customers to reflect and share the wisdom they’ve gained from their experiences can create an interesting conversation that allows you to form a deeper connection with them.

Asking them about the top advice they’d give to their younger self would motivate them to tell stories about their lives, revealing more about who they are as a person. Plus, it gives you an idea of what they value and how you can tailor your solution to meet their specific needs.

11. What is the best Netflix show you’ve enjoyed recently?

This is a great conversation starter as it’s both light-hearted and allows you to tap into shared interests. Plus, who doesn’t love talking about their latest Netflix binges?

Not only will this question help break the ice and keep the conversation flowing, but it will also help you form a deeper connection with your prospects. It can be an excellent way to get them talking more openly about themselves and their interests, which in turn could lead to other topics that are more relevant to your product or service.

We’ve said it before and we are saying it again: the goal should be to have an authentic, meaningful conversation with the customer, rather than coming across as pushy and fake.

Building Rapport Is a Journey, Not a Sprint

While you want to make as many connections as possible, it’s even more important to add value to every conversation. Every connection gives you a chance to make a memorable impression, so take advantage of the opportunity to make genuine connections with your prospects.

Salespeople build good relationships by asking the right questions. And, like any good relationship, it takes ongoing nurturing and a genuine interest to strengthen it. Be consistent in your interactions so your relationships are always moving forward.

When you prioritize asking rapport-building questions, you have a better chance of standing out for all the right reasons.

As well as asking rapport-building questions, you need to spend time on building rapport – before, during, and after your interactions with prospects and leads. Here are our six best practice tips for building rapport.

6 Tips for Building Rapport In Sales with Your Prospects

1. Do Your Research

You’re at a party. A friend introduces you to someone new. If your friend is a good host, they’ll probably tell each of you a couple things about the other. For example, “This is Jack, we used to work together at Company X and he’s a big baseball fan. Jack, this is Matteo, we went to school together in Chicago and he loves motorbikes.”

Ultimately, it’s easier to strike up a conversation centered around shared interests and experiences when you know something about the other person.

Sales is no different. You should always look into your prospect’s background before reaching out to them for the first time.

Presumably, you already know where they work and what their job is – that’s the whole reason they’re a prospect in the first place. But you need to dig deeper if you’re going to build rapport based around common interests. As a minimum, you should attempt to find out:

  • Their hometown
  • Where they went to school
  • What they studied
  • How long they’ve been in their job
  • Whether you have any mutual connections

2. Give (Genuine) Compliments

Compliments can be one of the greatest tools to help you build rapport – but only when they’re genuine and meaningful.

Let’s say you’ve researched your prospect on LinkedIn. It probably won’t advance your cause if you congratulate them on a recent promotion and tell them how much they deserved it – after all, they don’t know who you are, and they’ve almost certainly been inundated with “Congrats!” messages already.

On the other hand, if you see a piece of content that your prospect created and shared, it’s absolutely a good idea to read it, gather a couple of takeaways, and tell them how much you enjoyed it. Explain why you liked it:

Have you:

  • Been able to implement any changes to your own methods or processes having read it?
  • Shared it with your colleagues or other prospects?
  • Learned something particularly valuable from it?

That’s a proper compliment, and it paves the way for a wider conversation.

3. Take the Personal Approach

Sure, you’re ultimately trying to make a sale. Your prospect knows that. But that doesn’t mean you’re only allowed to talk about work.

Both you and the person at the other end of the line have a life outside of the office. Often, it’s the personal touches – a shared love of a certain TV show, restaurant, activity, or anything else – that can really help you make a connection.

I’m not saying that your first call with a prospect should be 15 minutes of quizzing them about their favorite book or movie. Instead, the personal approach should follow naturally from your initial research.

Here’s an example: you’ve found out they got an MBA at the University of Arizona. One of your closest friends went to UA too and studied at the same program. They told you about a certain professor who really brought the course material to life – does your prospect remember them?

4. Get a ‘Yes’ As Soon As Possible

Buyers are busy. Whether you’re cold calling them or previously made an appointment, it’s unlikely that speaking to you will be their highest priority for the day. That means they’ll naturally want to say “no” as soon as possible and get back to their to-do list.

The most effective way to combat this? Get them to say “yes” as early in the call as possible. Getting that first “yes” removes a huge barrier to your rapport-building efforts and paves the way for more “yes” responses down the line.

Best of all, it doesn’t need to be a difficult “yes.” You don’t have to ask them if they want to learn about your product or are available for a meeting next week. A positive response to even the most basic of questions – “Are you the best person to speak to about your company’s email marketing?” or “Can I email you a couple of free resources that will save you time on your email marketing?” – gives you an opening to strike up a real conversation.

5. Tell a Story

If I told 100 people that the average temperature in the Sydney Opera House Concert Hall is 72.5 degrees, how many of them would remember it a week later? Half? A third? Probably much less.

Now, imagine I told that same group that the reason for this is because a constant temperature of 72.5 degrees helps to keep the musicians’ instruments in tune. That’s a lot more memorable, right?

Why? Because it’s not just a fact, presented without context. It’s part of a story.

Stories capture the imagination; they help us to picture a scenario or challenge in a way that mere numbers never could. As a sales rep, you can use this effect to your advantage to forge closer bonds with prospects.

For instance, let’s say you’re talking about a client success story. Don’t just reel off cold, hard figures – how much their revenue increased by, or how many more leads they generated. Create a compelling narrative. What problems was the client facing? What did they say when you started working together? How did you come up with a solution? What speed bumps did you face along the way?

6. Add Value Early

Buyers need to understand that you know what you’re talking about and are worth listening to. If they start to question this, you’ll never succeed in building rapport.

Overcome these doubts by adding value as early as possible. Make it immediately clear to your prospect that they’ll enjoy real benefits by speaking to you, and always give them a reason to keep listening.

Say you’re speaking to a tech CFO. Prior experience with similar clients has taught you a few of their likely pain points – for instance, maybe their team is spending too much time maintaining spreadsheets and not enough on delivering analysis and insight to the board. But you can recommend a couple free tools that could make a big difference, based on what you’ve seen work in other organizations.

That’s real value. And best of all, because you’re not actively selling something at this point, it’ll help build trust too.

Remember: You’re Speaking to a Real Person

If you only take one thing away from this article, let it be this: never forget that you’re speaking to a real person.

All the rules that apply to “normal” (out-of-work) conversations are true of sales calls as well. The more relaxed and natural you can be, the more likely it is that you’ll build the rapport needed with your prospects to move business decisions forward.

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