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65 Instantly Memorable Rapport-Building Questions to Ask Your Customers

“This is Mateo.”

“Hi Mateo,” you say enthusiastically. “It’s Jessica from Marchbank … So, how was your weekend?”

“Great,” Mateo responds. “ … How was yours?”

“Awesome,” you reply. “And uh … how is the weather by you?”

“Um … it’s warm. So that’s good.”

You’re probably bored just reading this conversation. So why do customer support reps use these types of generic opening questions in real-life conversations with customers?

Unfortunately, many reps default to stock questions for simplicity’s sake. They’re easy and safe, yes, but there’s a downside: They make it harder to build true rapport.

The conversation with Mateo didn’t have to start off this way. Imagine if, instead, you’d said:

“Hi Mateo, it’s Jessica from Marchbank. I saw someone from your town was on Shark Tank last night! Do you know Brett Finnigan?”

Even if Mateo has never met Brett in his life, this question is far more engaging and memorable than “How was your weekend?”

However, crafting the right rapport-building questions can be tricky. To master this skill, check out what goes into a great one -- then borrow some of our 65 ideas.

Anatomy of a Memorable Rapport-Building Question

An effective rapport-building question meets three criteria:

  1. Personalized. People tend to blow off questions like “What’s the weather like?” or “Got any fun plans for the summer?” because these could be asked to -- and answered by -- anyone. If you ask a highly specific question, however, you’ll show you’re actually interested in the answer (and by association, the customer).
  2. Unique. Your question should be a little unexpected. By catching the person off-guard, you’ll get a more honest answer -- and honesty breeds intimacy.
  3. Appropriate. Even though your question should be surprising, it shouldn’t be surprising in a bad way. Avoid anything that could be seen as nosy or out-of-bounds. For example, if the customer says, “I just got back from a conference in Atlantic City,” don’t reply, “Nice! Did you get a chance to party?”

And now without further ado, here are 65 unique rapport-building questions for use on your next call or in your next email, broken out by topic.

Location Questions

  • I see that you’re in [city]. What’s the best part about living there?
  • Is it true what they say about living in [city/state]? (For example, “Is it true what they say about living in L.A.? Are the freeways essentially parking lots?”)
  • Since you live in [city/state], do you go to [local attraction] all the time?
  • I have such good memories of [city/state] -- I visited when I was X years old and absolutely loved [destination/feature]. What do you think about [destination/feature]?
  • If I had the opportunity to pass through [city/state], what would be your top recommendations?
  • Is [city/state] a good location for [customer’s industry/company/profession]?
  • I’ve heard [nearby restaurant/city/state] has amazing [food item]. Does it deserve the hype?
  • What's your commute like? (Do you drive, take public transit, carpool, etc.)
  • What brought you to [city/state]?
  • What's something most people don't realize about [city/state]?
  • Are there a lot of companies in [customer's industry] in [city/state], or are you guys fairly unique?
  • Is [city/state] where your company is located, or do you work remotely?

Job and Career Questions

  • My [niece/son/grandchild] wants to become a [profession]. Do you have any advice I should pass on?
  • I saw you used to work in [different field/profession/industry]. How was the transition?
  • Do you go to [well-known industry event]? Why/why not?
  • You tweeted about going to [conference] -- have you been before? I’m debating whether or not to go, and I’d love to hear your thoughts.
  • My friend used to work at [current or former company]. Do you know [name]? What was it like working there?
  • As a rep for [company], I talk to a lot of people in [customer’s profession], but you’re the first I’ve met who’s ever majored in [unexpected major]! How’d that happen?
  • I read on your LinkedIn that you spoke at [event] -- really impressive. Do you have any future speaking events lined up?
  • I noticed you have your X certification. What was the process of getting that like?
  • On your LinkedIn profile, you listed [unusual skill] under your Skills. How often does that come in handy?
  • You’re fluent in [second language], right? Wow! Do you travel to [country] fairly often? Do you use [language] in your work? Is there a third language in your future?
  • What's your favorite aspect of your job?
  • Many of my clients in [customer's role] tell me [X detail about job]. Has that held true in your experience?
  • I'd love to learn more about [customer's role]. Are there any resources you'd recommend?
  • Why did you decide to work in [customer's field]?
  • My [niece/son/grandchild] wants to become a [profession]. Are there any subjects you'd suggest majoring in?
  • What job would you want if you weren't a [customer's profession]?

School and Interest Questions

  • You’re an alum of [college]! My friend graduated from [college] in [year]. They said it was really X … (Or, “I’ve never met anyone who went to [college] before! What was it like? Would you send your kids?”)
  • I noticed on LinkedIn that you help out with [organization]. How’d you get started with that?
  • Saw on Twitter that you’re a massive [sport] fan. Are you looking forward to [related event]?
  • In your LinkedIn summary, you mention loving [activity]. How long have you been doing that?
  • Just noticed you attended [school]. What was it like going to college [in the South/on the West Coast/in a big city/in a small city/etc.]?
  • While I was preparing for our conversation, I noticed you follow [influencer] on LinkedIn. What did you think of their ideas on [topic]? (Alternatively, “Did you read their book?”)
  • I saw you follow [influencer] on Twitter -- I do, too. Did you see what they wrote the other day about [topic]?
  • I saw on LinkedIn you attended [college]. My [niece/son/grandchild/family friend] was thinking of applying. What was your experience like?
  • Do many people from [college] end up in [customer's current location]?
  • Would you go back to [college] again for a graduate degree?
  • Are there any leaders in your space you'd recommend following?

Content- and Activity-Based Questions

  • You recently tweeted a link to [podcast/radio show]. Have you listened to [specific episode/similar show]? (This question also works for books, movies, and TV shows.)
  • I loved what you [blogged/shared] the other day about [topic]. Have you read [related article]?
  • Since you’re interested in [topic]; I was wondering if you’d read [book on topic]?
  • I saw that you tweeted about [author/book name] -- I’m looking for a new read, should I try [author/book name]?
  • I’m putting together a list of great blogs for [customer’s industry]. Do you have any recommendations?
  • I’m putting together a list of must-read blogs for any [customer’s profession]. Which ones do you like?
  • I’m buying a book for someone’s [milestone year] birthday. Do you remember reading anything around that time that really changed your life?
  • I saw on [LinkedIn/Twitter/Facebook] you're interested in [topic]. Do you have any related documentary recommendations?
  • I saw on [LinkedIn, Twitter, Facebook] you're interested in [topic]. How did you [learn about, come across] that [topic, field]?
  • Do you subscribe to any newsletters about [topic, industry, product category]?
  • I read the [article, blog post, interview, white paper, ebook] you shared on [topic] on [LinkedIn, Twitter, Facebook, etc.] What did you like about it?

Company Questions

  • Congrats on [recent company announcement]! How long was that in the works?
  • I saw [company] won [award] recently -- way to go. Did you submit an entry, or were you unaware your team was up for consideration? Who were you competing with?
  • Your company just [opened up/moved to] a new office, right? What’s the [neighborhood/city] like?
  • I saw on Twitter [you/your company] just started using [non-competitor product]. We were thinking of trying that one out -- what’s been your experience so far?
  • Your company’s retreat photo came up on Instagram. Did you like [destination]? What was the highlight of the trip?
  • I was browsing your company’s site when I came across the blog. I loved [your/your coworker’s/your CEO’s] post about [topic]; what do you think about [related topic]?
  • I came across [company's] social media accounts while I was preparing for our call. It seems like a [fun, interesting, fast-paced] place to work. What do you think?
  • I learned about [company's] unique tradition of [doing X] on [your company blog, social media]. How did that tradition begin?
  • I learned about [company's] unique tradition of [doing X] on [your company blog, social media]. Is that your favorite tradition?
  • Your company seems to host [online events, customer events, recruiting events, philanthropic events, industry events] fairly often. Are you involved in those?

Random Questions

  • I read on [LinkedIn/Twitter/your blog/etc.] that you think [opinion]. I feel the same way -- but I’m always curious to learn how other people formed their opinions. How’d you come to this one?
  • You seem to have a pretty busy schedule. Do you have any productivity tips?
  • It seems like you’re fairly busy -- do you use apps to stay organized? I’ve been looking for a good one, so recommendations would be helpful.
  • You seem like someone with good Netflix picks. What have you enjoyed recently?
  • Have you read any good books lately?

By showing interest in your customers and getting them to open up, you can deepen even the most transactional relationships. And once you’ve created that trust? You’ll see a dramatic change in your ability to solve their problems and turn them into loyal customers.

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