How To Utilize Rapport-Building Questions

Sometimes, we meet a stranger who we just seem to “click” with. There is instant mutual understanding and trust. It feels elating.

That feeling is called rapport, and it can be manufactured. All you need to do is to ask the right rapport-building questions.

Learn how rapport benefits your business and personal relationships, what boxes a good rapport question must tick, and which pitfalls to watch out for.

What Is Rapport?

Rapport means having a deep connection with another person. This allows you to move beyond the surface level of an interaction. You can now freely communicate with the other person, even about intimate topics.

There are two key ingredients for rapport:

  1. Sympathy. If we find someone likable, we are more likely to open up to them.
  2. Mutual trust. We need to feel sure that the other person won’t betray our trust if we confide in them.

Rapport has a huge impact both on your business and on your personal life.

In business, rapport will make you more money. When you have a rapport with your customers, they will order more products. When you have a rapport with your boss, he will pay you more.

In your personal life, rapport will create more happiness. When you easily get into rapport with others, you will have better romantic options and more fulfilling friendships.

The best way to create rapport is to use rapport-building questions. They allow you to initiate the process at will, or speed it up, when needed, e.g., if you want to close a sale before the quarter is over.

Benefits of Building Rapport

The ability to create rapport comes with several benefits.

Less Friction

Rapport erases social friction. That is useful if you suffer from office drama. Learn how to connect with co-workers, and your own life will get much easier.

The same is true if you are running a team. Befriend everybody, and people are more likely to take your requests seriously.

Better Chances of Advancement

If you are known as the person who gets along with everybody at the office, you are more likely to get promoted.

Lower Churn Rate

If your customers trust and like you, they will keep buying from you. That is especially useful in industries with a high churn rate, like marketing.

More Data

When you have a good rapport with clients, they will share more information about themselves. This is useful for creating more accurate customer personas.

It is also useful in a personal context, e.g., when you have a crush on somebody. You can now better understand what they value and play to these values (if you so choose to).

More Lenience

We are more lenient with people we have a rapport with. For example, your long-standing customer is more likely to forgive a slip-up than a new customer that you never talked to you.

More Closes

Bad salespeople act pushy. They think they can force the customer in a certain direction. That is off-putting.

Good salespeople do the opposite. They inform you about the advantages and disadvantages of a product, while constantly increasing rapport. You end up buying from them because you trust them more.

More Differentiation

All other factors being equal, we tend to buy from people we like.

That’s why rapport is so important in the B2B world. Here, products often look the same; the only real differentiator is the personal touch.

More Influence

While you can’t fundamentally change people, you can amplify pre-existing inclinations. And the way to do so is rapport.

For example, if your overweight friend is on the brink of joining a gym, you can tip the scales by offering encouragement. Since they like and trust you, they are more likely to listen to you.

The Anatomy of a Rapport-Building Question

The ideal rapport-building question must tick five boxes. It should be:

  1. Personalized. The question must relate to the other person — their life, their values, their ambitions, their pains. Only then will the other person feel seen.
  2. Revealing. If you show yourself as vulnerable, the other person is more likely to show themselves as vulnerable too.
  3. Calibrated. Don’t ask a client about their religious beliefs; don’t ask your mother-in-law about her sexual preferences.
  4. Non-needy. We want to build rapport, but without getting too buddy-buddy. Nobody respects a suck-up.
  5. Contextual. If you just ask random rapport-building questions without context, people will get annoyed with you.

How To Get Your Hook In

The challenge with rapport-building questions is that you are fishing. You are trying to come up with a topic that resonates with the other person, to bring them to open up.

But how do you do that when you know nothing about them?

To make things more challenging, you only get a limited number of tries. Nobody likes to be asked 50 random questions in a row. It feels too much like an interrogation.

The solution is to go after topics that apply to anybody because they are universal to the human experience. At the same time, these topics must still be meaningful to us.

Here are a few starting points:

  • The place we live in
  • The people we live with
  • The things we do to survive
  • The things we do for fun
  • The things that interest us
  • The things that annoy us
  • The things that scare us

I also recommend that you pick topics that you are currently excited about yourself.

We like to think that we are all terribly individualist and different. But in reality, most of us are wired very similarly. So, it is safe to assume that whatever gets you moving emotionally, is also on the mind of other people.

Thus, watch yourself. You are excited about buying a new car? You are worried about the recession? You secretly dream about traveling the world? Whatever is on your mind, assume it is on other people’s minds as well. So, ask them about it and watch how quickly you will bond with them. This works so well because the other person can feel your enthusiasm, and that energy is infectious.


Please note that the examples given must be adjusted to the person you are talking to.


  • “So, I understand you are not originally from Sacramento. What made you move there?”
  • “Whenever someone brings up Columbus, I think of the Buckeyes first. Are people really that crazy about college football there? Are you?”
  • “Do you live inside or outside the city? What’s your commute like?”


  • “My niece is also thinking about going into computer science. Is there an area of expertise that you would recommend over others?”
  • “I saw you used to work in the finance industry. What was the transition like for you?”
  • “You posted about Hubspot’s INBOUND conference recently — have you been before? I am thinking about attending myself.”


  • “I saw you’re a Georgetown University alumnus. My best friend graduated from there in 2006. He always tells me clubs were such a big part of campus life. Were you in any clubs?”
  • “As a sales rep, I talk to a lot of people in the IT industry, but you’re the first one I’ve met who majored in Eastern European Studies! How did that happen?”
  • “A colleague of mine recently went back to school to get his MBA, and he got me thinking. Did you ever consider that for yourself? What is your take on continuous learning?”


  • “Sally told me you are really into Game of Thrones. What was your favorite episode?”
  • “I used to play the guitar when I was younger but wasn’t very good at it. Do you have any artistic interests?”
  • “I am still a little bit stiff from BJJ training last night. You look pretty fit yourself. What do you do? Lift weights?”


  • “I really liked your critical take on AI for content creation. It leads to uninspired, mediocre writing at best. How was that received? Did you get a lot of pushback?”
  • “When you say American politics are too caught up in a black-and-white mindset, what are some ways to overcome that?”
  • “Your stance on radical self-accountability is really refreshing. Do you have any books or other materials that you can recommend?”


  • “I saw your company recently acquired a new tech start-up. Were you involved in that?”
  • “You guys are currently implementing several new technologies. Which one do you think has the greatest potential?”
  • “You recently merged with another big player in your industry. How did the transition go for you? Were there any hiccups?”


  • “Brian talks highly about you, especially your out-of-the-box thinking. How long do you guys go back?”
  • “My daughter just got accepted into Berkeley, I am very happy for her. Which colleges do your kids go to?”
  • “My Italian relatives from Sicily come to visit me each year, it’s a pasta fest. Do you have relatives abroad?”

How To Build Rapport

It is not just enough to memorize a few rapport-building questions — you must also embed them in a strategy. Here is how you do that.

1. Don’t Skip Phases

Conversations consist of three stages that build onto each other:

  1. The Proposal Stage (“Here is what I want from you”)
  2. The Rapport Stage (“Let’s see if we click”)
  3. The Close (“It’s a deal”)

This very basic structure applies to any kind of interaction — business deals, making friends, flirtatious conversations.

The biggest mistake you can make is to get the order of these phases wrong. For example, don’t go straight into befriending your potential customer if you haven’t made it clear you want to sell to them yet. You will be seen as disingenuous.

Likewise, don’t go straight into rapport with a romantic interest, if you haven’t stated your sexual intent yet (“I just saw you from across the bar and thought you looked very attractive”).

You also don’t want to jump straight to the close. That will only work if the other party desperately wants what you are offering at this moment, and there is no alternative to be had. But those are very slim chances.

2. Do Your Research

In the past, when you were building rapport, the stranger across you was a blank page. You would have nothing to go on.

Now, with a prospective client or a new date, you can always check their social media first. You can read their bio on LinkedIn, check out their vacation pics on Instagram, or learn about their political leanings on Twitter.

This will give you a massive edge when you are building rapport, as you already have an idea of what their life looks like. Just be careful to weave it in subtlety to not come across like a stalker.

3. Tailor Your Questions

Every situation is different. Every client is different. Hence, you should tailor your rapport-building questions to the person in front of you.

People can tell when you are using canned material from your last sales seminar. It sounds formulaic and robotic. It’s much better to fumble around a little bit on the spot but be seen as making an effort.

4. Avoid Interview Mode

Don’t ask too many rapport-building questions in a row. It puts people on the spot as if they were in an interview situation. Eventually, they will become monosyllabic or stop answering your questions altogether.

To avoid that, always make sure to intersperse your questions with statements of your own.

For example:

You: “I saw you like to go fishing on Instagram. What’s the biggest fish you have ever caught?” [question 1]

The other person: “I once caught this giant catfish, it was like 40 pounds, blah blah blah.

You: “That is crazy. I think the biggest one I ever caught was like 8 pounds. It was with my dad when I was younger. [interspersing statement] You still go fishing with your dad, right? [question 2]

5. Pay Attention to Delivery

The best rapport-building question will do little for you if your delivery is off. Your posture, your gestures, your tonality, your eye contact — all of that matters. It’s what decides if you are perceived as a likable, self-confident conversationalist or a needy supplicant.

The two best ways to get this straightened out are to practice your delivery in front of a mirror, or, better yet, to record yourself. The latter has the advantage that you can play the recording to another person and get their feedback on your nonverbals.

6. Use Their Name

It’s an old sales trick, but it still works — if you use somebody’s name throughout a conversation, they are likely to react favorably to you. Hearing our own name woven into the conversation makes us feel like we matter.

Do this sparingly, though. Two times throughout a 10-minute conversation is already plenty. Any more than that, and you risk sounding like a used-car salesman.

7. Use Touch

Lightly touching somebody throughout an interaction is an instant rapport builder. It breaks down the unseen barrier between two strangers and replaces it with friendly familiarity.

Obviously, only touch people in places that are socially acceptable, like at the shoulder and with the back of your hand. And even so, do this sparingly. Once or twice in an interaction is perfectly fine, but 10 or 20 times is creepy.

8. Bridge the Gap

The sales process often takes place in stages. You have one interaction with a potential customer, then three days later, you have another one. Especially with expensive B2B goods, a final purchase decision might be weeks out.

Therefore, it’s important to re-establish rapport every time you have another interaction, as rapport is lost over time.

This doesn’t have to take up a lot of space. Just revisit some of the rapport topics that you last talked about (“So, did you go to that gold tournament as you had planned?”).

It’s best if your customer always ends up talking to the same rep, as it’s easier to recover rapport with someone you had it with before. But if you must switch reps, make sure to pass on rapport pointers to the next person in charge.

9. Switch It on and Off

Finally, it’s worth considering why we are so hung up on rapport (especially in sales and dating) in the first place.

I would argue it is because we as a culture believe we should get along with everybody. We should close every client, befriend any stranger, or charm any date.

However, that can lead to some serious disappointments down the road. When you always put up a super likable front, it is harder to be seen for who you really are. As a result, you attract people you are not really compatible with.

Having said that, if you are completely clueless when it comes to building a deep connection with others, you will also have a hard time, be it in business or in life.

The answer is somewhere in the middle.

At one point in your life, you absolutely want to make a study of connecting with people and getting them to like you. You need that skill set.

But once you have taken that to a certain level, now it’s time to evaluate. Do you really want to charm just anybody? Probably not. You are better off turning that skillset on and off as needed, depending on your objective.

So, at a job interview or closing a new customer? Bring the charm. But talking to strangers at a party or going on a date? Risk showing yourself as you are. You’ll end up with better people.

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