How To Utilize Rapport-Building Questions

Sometimes, we meet a stranger who we just “click” with. There is instant mutual 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 is a state of deep connection between two people. It allows you to communicate freely and meaningfully.

There are two key ingredients for rapport:

  1. Sympathy. If we find someone likable, we are more likely to open up to them.
  2. Trust. We need to feel sure that the other person won’t betray us 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 an excellent rapport with your customers, they will order more products. When you have a great 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 more fulfilling friendships and better romantic options.

The best way to create rapport is to use rapport-building questions. They allow you to initiate the process or accelerate it.

Benefits of Building Rapport

The ability to create rapport with somebody comes with many benefits.

Less Friction

Rapport reduces social friction. For example, if you learn how to win over your co-workers, you will experience less office drama.

Better Chances of Advancement

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

Less Attrition

If your customers trust 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 will give you better market insights.

More Lenience

We are more lenient with people we have rapport with. For example, a trusted friend is more likely to forgive a slip-up than a stranger whom you just met.

More Closes

If you are good at establishing rapport, you will close more deals. We buy from people we like.

More Differentiation

Rapport can also act as a differentiator. This is especially important in the B2B world, where products often look the same. The personal touch will tip the scale in your favor.

More Influence

When people trust you, they are more likely to listen to you. For example, you might persuade your overweight weight friend to go to the gym with you when nobody else can.

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 open up too.
  3. Calibrated. Don’t ask a client about their political affiliations; don’t ask your mother-in-law about her sexual preferences. Be appropriate to the situation.
  4. Non-needy. We want to build rapport, but without getting buddy-buddy. Nobody respects a toady.
  5. Contextual. If you just ask random rapport-building questions without context, people will get annoyed with you.

How To Get the Hook In

With rapport-building questions, you are essentially fishing. You are trying to come up with a topic that resonates with the other person.

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

To make things more tricky, you only get a limited number of tries. Nobody likes to be asked endless questions. It feels like an interrogation.

The solution is to go after topics that anybody can relate to because they are universal to the human experience.

Here are a few starting points:

  • The place we live in
  • The people we live with
  • What we do to make money
  • What we do for fun
  • The things that interest us
  • The things that annoy or scare us

Another trick is to inquire about topics that you are excited about.

You are excited about buying a new car? You secretly dream about traveling the world? Start there.

It works because your positive energy is infectious. Even if the other person is not interested in the topic per se, they will enjoy feeding off your enthusiasm.


Here are some example questions to show you how to put these principles into practice.


  • “So, I understand you are not originally from Sacramento. What made you move here?”
  • “Whenever someone mentions Columbus, I think of the Buckeyes. Are people really that infatuated with college football up there?”
  • “Since you live outside the city, what’s your commute like?”


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


  • “I saw you’re a Georgetown alumnus. My best friend graduated from there. He always tells me that clubs are 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! What’s the story there?”
  • “A colleague of mine recently went back to school to get his MBA, and he got me thinking. Did you ever consider going back to school?”


  • “Sally told me you are really into Game of Thrones. Who is your favorite character?”
  • “I used to play the guitar when I was younger. I was bad, but I loved it. Do you have any artistic interests?”
  • “I am still a bit stiff from BJJ training last night. You look super fit yourself. What is your activity of choice?”


  • “I liked your critical take on AI for content creation. I agree, the results sound generic. How was that received? Did you get pushback from the AI crowd?”
  • “You said American politics are too caught up in black-and-white thinking. Do you have some ideas on how to overcome that?”
  • “Your stance on accountability is refreshing. Do you have any books that you can recommend?”


  • “I saw your company recently acquired a new tech start-up. Were you involved in that process?”
  • “You guys are currently implementing several new technologies. In your opinion, which one has the greatest potential?”
  • “Your organization recently hired a new CMO. Do you work with her directly? What is she like?”


  • “Brian always talks highly about you. How long do you guys go back?”
  • “My daughter just got accepted into Berkeley, she is so excited. Your daughter is about to graduate, right?
  • “My Italian relatives from Sicily visit me each year; it’s a pasta fest. Do you have relatives from abroad?”

How To Build Rapport

It is not enough to memorize a few rapport-building questions — you must embed them in an overall 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 basic structure applies to any kind of interaction — business deals, making friends, sexual interactions.

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 yet you want to sell to them. You will be seen as disingenuous.

Likewise, don’t go straight into rapport with that hot thing at the bar, if you haven’t stated your sexual interest yet. You’ll get friend-zoned.

Neither do you want to jump straight to the closing phase. It might work one out of a hundred times. But you will leave many good opportunities unexploited.

2. Do Your Research

In the pre-digital age, most people you met were unknown to you. You had 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 building rapport, as you already have an idea of who they are.

Be subtle, though. You don’t want to come across like a stalker.

3. Tailor Your Questions

People can tell when you are using canned material from your last sales seminar. It sounds formulaic.

You must always tailor these materials to the person in front of you.

If that means stammering around a bit, so be it. It’s still better to be seen as authentic.

4. Avoid Interview Mode

Don’t ask too many rapport-building questions in a row. It feels too much like an interrogation. Eventually, the other person will disengage.

To prevent that, always 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 ever caught?” [question 1]

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

You: “That is crazy. I think the biggest one I ever caught was 10 pounds. It was with my brother. [interspersing statement] Do you have siblings? [question 2]

5. Pay Attention to Delivery

The best rapport-building question will accomplish little if your delivery is off.

Your posture, your gestures, your tonality, your eye contact — all of these matter. It’s what decides if you are perceived as a pleasant conversationalist or a needy supplicant.

There are two ways to go about this.

You can practice your delivery in front of a mirror as an actor or a salesperson would.

Or you can record yourself. The advantage is that you can play the recording back 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. Done right, it removes the unseen physical barrier between two strangers.

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

8. Bridge the Gap

The sales process often takes place in stages. You have one interaction with a potential customer, then 2 weeks later, you have another one. Especially with expensive B2B goods, a final purchase decision might be months out.

With each of these points of contact, it’s important to establish rapport anew, as rapport is lost over time.

Just revisit some of the rapport topics that you last talked about (“So, did you end up participating in that golf tournament?”).

It’s best if your customer always talks to the same rep, as it’s easier to recover rapport with someone you already know than starting from scratch with a new person.

But if you must switch reps, make sure to pass on rapport pointers to the next person in charge. CRM software is great for that.

9. Be Strategic

Rapport is a cultural institution, especially in the US. From an early age, Americans are trained to be endearing.

But this also comes with risks.

When you always put up a likable front, it is harder to be seen for who you really are. As a result, you will attract people who you are not compatible with.

What I am saying is you that should frame rapport as a tool in your toolbox — not as your default mode of being.

By all means, make a study of connecting with people. You need that skill set.

But once you have taken that to a certain level, become strategic about it. Do you really want to charm just anybody? Probably not. You are better off turning that skill on and off as needed.

At a job interview? Bring on the charm. But when making new friends? Risk showing yourself as you are, idiosyncrasies and all. You’ll end up with more fulfilling relationships.

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