Try This Insanely Easy Rapport-Building Exercise to Boost Your Charisma

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Aja Frost
Aja Frost



As soon as the man in front of me takes out his wallet to pay, my heart starts beating a little faster. T-minus five seconds.

The checkout person hands over his receipt, he grabs his groceries, and… I’m up.

“So, how’s your shift going?” I ask the checkout person.

My goal: Create a genuine connection with her in the time it takes her to scan my purchases and ring me up.

The Rapport Building Game

I play this game every single time I go through the line at the grocery store, and while you might think it sounds crazy, hear me out: Since I started doing this two months ago, my ability to quickly build a rapport with a total stranger has improved dramatically.

Why You Should Try This Exercise

Research shows that humans primarily use emotions -- not logic -- to guide their decisions. So even if you’re selling the best product on the market with the most advanced features and the most competitive price, you’ll still lose customers to the sales rep that people trust more.

The solution? The first step to trust is having a genuine connection with someone. So get really, really good at forging connections. And since you usually don’t have much time with a prospect (or a networking contact, or a hiring manager, or anyone else on which you need to make a good impression), you need to get really, really good at forging connections really, really quickly.

How quickly? Like in the one minute it takes to check out at the grocery store.

By playing this game, you’ll get the opportunity to practice your rapport-building skills in a zero-stakes environment. As an added bonus, you’ll get to make others’ lives a little more pleasant -- and you may even start to enjoy your grocery runs.

Now that you’re sold (pun intended), I’ll share the details.

How to Get Started

First, let’s define what a “genuine connection” means. It’s a little like obscenity -- you know it when you see it (or in this case, experience it). I usually award myself a victory when the checkout person flashes an authentic smile, laughs, or shares a unique personal detail. (Oh, and if the conversation is engaging enough that another customer in line jumps in? Bonus points!)

If the person is polite but disengaged, on the other hand, I chalk it up as a loss.
I typically get the ball rolling with a question. Normally I’d recommend leading with a personalized question, but that won’t work here for obvious reasons.

Try one of these instead:

  • “How’s this [day of the week] treating you?”
  • “How’s your shift going?”, then “Do you still have a long time left?”
  • “Have you tried [product I’m buying]?”

Alternatively, start with a compliment. I told a woman her blue hair was gorgeous and bold (prompting her to launch into a rendition of her friends’ reactions to the dye job -- win) and an older man I loved his whimsical bowtie (leading to the story of how he got it -- another win). Appealing to something a person is proud of will immediately endear them to you.

After you’ve asked a question or given them a compliment, look for something in their answer you can spin into a conversation.

For example, here’s the interaction I had yesterday:

Me: How’s your shift going?

Checkout man: Pretty good! I mean, life’s good.

Me (with a smile): Glad to hear that! Anything in particular making you happy?

Him: I don’t know, I have running water, a roof over my head, food when I’m hungry…

Me: What an awesome outlook on life.

Him: Honestly? I’m always watching documentaries and reading about different places so I can keep things in perspective. So many people I know take this all for granted.

And there it was: The moment of honesty and openness that defines a true connection.

5 Additional Icebreaking Questions

“Have you tried those dark-chocolate-covered almonds yet?” is an effective conversation-starter when you’re at the store, but it’ll probably (read: certainly) fall flat elsewhere.

So, when you’re trying to practice creating connections in other contexts, try these instead:

1) “You seem like you’re in a good mood! What’s your secret?”

Use this one if someone’s smiling: People love being told they look happy, and you’ll get to hear about the last nice thing that happened to them.

2) “So, where are you headed after this?”

Whatever they say—work, home, the dog park, dinner—you’ll get fodder for a follow-up question.

3) “I know this is random, but what’s the last show you binge-watched? I just finished binging [show].”

This one has never failed me. Admitting you binge-watch to a stranger is weirdly disarming, so you’ll immediately create some trust. In addition, everyone enjoys swapping show suggestions.

On the rare occasion they say, “I don’t really watch TV,” you can reply, “Wow, that’s impressive! Teach me your ways -- I bet you’re pretty productive.”

4) “Do you live around here? I’m looking for a good [service, product] and would love a recommendation.”

There’s really only two responses to this: “Yes, I do! Have you tried…?” and “Sorry, I’m not from here.”

If it’s the latter, say, “Ahh, then my search continues. Where are you from?”

5) “Did you get your [shirt, pants, shoes, bag, etc.] from [store]?”

It doesn’t matter if you’re totally off -- they’ll correct you, and then you’ll be talking!

How to Use What You Learn

In just a month, you'll start noticing trends: What makes people light up, what keeps them in “polite but uninterested” mode, and which elements of their response to hone in on. These insights will be invaluable when you call strangers or meet them in person -- after all, you'll have an arsenal of statements and questions that'll likely shatter the proverbial ice at the ready.

But by month two (where I am), you'll probably stop needing an arsenal at all. You'll have become practiced at reading people and knowing intuitively what to say to create a genuine connection.

So go ahead, go run some errands. It’s good for your career.

HubSpot CRM

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