The Simple Trick That Helped a Shy Introvert Become Great at Sales

Bonus: I had better relationships with my coworkers, too!

“You’re a sweet girl, Abby, but…” my coworker trailed off, but she didn’t have to finish the sentence. I knew the ending was “you’re dumb as a brick.”

That’s how my new coworkers saw me, and probably customers, too. An introvert, I’d just stepped into my first retail job working at a high-end clothing chain. It took half my measly paycheck to buy a single blouse from the store — a real problem when you have to wear the clothes to work.

I needed that commission bonus the company offered. Like, needed it bad. I was a sophomore in college with books to buy and gas to pay for, and my check from the university’s work study program wouldn’t come until the end of the semester. But mostly, I needed it to prove I could sell with the best of them.

I tried everything. Memorizing the catalog, putting together outfits, and small talk (which, for this introvert, felt like slowly dying at the merciless hand of boredom). I greeted customers with a friendly smile and a breezy, “Let me know if you need anything.” Nothing worked.

What else could I do?

I’d always hated pushy salespeople and didn’t want to be one. But clearly, that was what it took. Sales, it seemed, was not for me.

I switched to a different job in a less high-stakes store and thought I’d moved on. Oh, the innocence.

Even though this new place didn’t have commission bonuses, their emphasis on team sales was something I overlooked in the interview. They expected each team member to contribute to sales; it just wasn’t tracked the same way as the first job.

Hello again, square one.

How I Got People to Like (and Buy From) Me

I get my introversion from both my parents, but my personality as a whole tends more toward my dad’s. We don’t like the shallow conversation that good salesmanship appears to depend on. But my father has been in the sales game for over twenty years, selling and designing kitchens for a wide variety of clients.

It made sense to ask my introverted salesman dad how to get better at it. Of course, selling clothes and selling kitchens are two completely different ball games, but I was sure the same principles could apply.

The advice he gave me? Get better at small talk.

A part of me died inside. Small talk was horrible, hell’s perfect scheme for crushing the soul.

At school, small talk was more bearable. There, at least, existed a set of questions to use like “What year are you?” “What’s your major?” and “What do you plan to do after graduation?” But in the real world, where there was no handy list of common denominators uniting me to the people I had to converse with, small talk was a thousand times harder and usually limited to sports events I didn’t follow and — lord help us — the weather.

As I mused over the pitfalls of the school bubble versus the real world, the simple trick hit me smack in the face: I needed a different set of questions.

That was it. That was the key for someone as shy and introverted as me to make small talk with complete strangers.

The Key to Small-Talking With Complete Strangers

I started with holidays. Whatever holiday happened to be up next was my weapon of choice. “Any plans for St. Patrick’s day?” “What Easter traditions do you have?” “Do you ever go to see the fireworks downtown on the Fourth?”

It seemed to work. Once people started talking about themselves, the pressure was off me, and they suddenly liked me a whole lot more. If they paused, I could throw in some inane tidbit about my own holiday plans, which usually got the ball rolling again.

Next, I tried current events. This didn’t work as well. I had no desire to scroll through an endless news app just to find an appropriate topic to discuss with a customer. Politics was a minefield. News quickly became depressing and didn’t put customers in a blissful, outfit-buying mood. Social commentary proved almost as dangerous as politics.

I tried a new tack: personal questions.

No, not “How’s your sex life?” or “What horrible thing did your mother-in-law do this week?”

If the customer had a baby, I’d ask how old the little one was. If they came in asking where they should look for business casual clothes, I’d ask them what they did for a living. If they were wearing a cat shirt, I’d ask if they had cats (be warned: This one might lead you down a feline-infested rabbit hole of cat photos and endless chitchat).

Usually, even if the answer was short, it provided material for another question. Sometimes it took three questions to really get them talking, but it almost always worked.

My sales went up. No, I didn’t sweep the floor with my coworkers, but I wasn’t dragging down the team anymore, either.

Now I Have to Convince People I’m an Introvert (*Sigh*)

After two years of working in retail, I quit to focus on my last year of school. Then, I graduated, and suddenly the bills became more important than waiting it out for the right job in my field. So, I fell back on my experience, what I was good at.

Yep, you read that right. I was good at sales.

Did I like high-stakes, commission-type jobs? No. Did I like getting to know people? Shockingly, yes! So I went to a thrift store, where the relationships with the people were more important than the dollars.

And I thrived.

By the simple art of asking questions, I’d learned to make friends with my coworkers quickly, keep the regular customers happy, and turn first-time shoppers into returning ones. Am I the best salesperson on the planet? No!

I don’t push items I know customers don’t want. That’s not my style. I help them find what they’re looking for, not what I need to sell. I talk to them, get to know them, remember their names, ask how their mother-in-law liked that Hummel plate set they bought last week. Thoughtful, focused attention is the superpower of any introvert.

Asking questions worked so well for me that I got comfortable with the employee-customer relationship. It worked so well that I got promoted to assistant manager. It worked so well that my boss once told me, “You say you’re an introvert, but I don’t think so,” and I had to spend an annoying ten minutes explaining what an introvert actually is. It worked so well that, when I finally left the thrift store life, even the customers were sad to see me go.


Join the introvert revolution. One email, every Friday. The best introvert articles. Subscribe here.


A Few Practical Tips

While the traditional route for extroverts in sales may be to push, push, push, there’s a better alternative for introverts and extroverts alike. Take the quiet road. Let people talk about themselves and their lives. You’ll build loyalty and friendship, and the sales will follow.

Here are some of the topics that helped me build a repertoire of go-to questions:

  • If there’s a holiday coming up, ask what their plans are.
  • If they mention or are with a significant other, ask how they met.
  • If they have or mention kids, ask how many they have, how old they are, etc.
  • If they’re wearing a shirt with a business logo, ask how long they’ve worked for the company, if they like working there, or what the company does.
  • If they’ve purchased something in the past, ask how the product worked out for them.
  • If they’re a regular (or a coworker you want to be on better terms with), find one topic you know they’re passionate about and ask about it every time you see them. (Side note: One customer owned horses, so I would always ask how her horses were when she came in; similarly, one of my coworkers was planning her wedding, and two others were teachers — easy topics to say, “Hey, how’s _____ going?”)

Introverts, I hope these tips help you whether you work in sales or just want to make a few new friends. What are your go-to methods for surviving and thriving in an extroverted world? Let me know in the comments below.

You might like:

Abigail K. Miller is a freelance writer and blogger who loves chai lattes and cool fall evenings. She graduated from North Greenville University with a Bachelor of Arts in English in 2018 and is currently writing a young adult fiction series. She’s an INFJ, a proud Hufflepuff, and an avid reader. You can learn more about her at her website, www.akmillerwrites.com, follow her on Instagram @akmillerwrites, or check out her blog, www.indigotypewriter.com.