Throughout college, I worked 25 hours a week as a sales associate at an intimates boutique that specialized in comfortable and supportive bras for large cup sizes.

While I was paid hourly, a good chunk of my income came from commission from the sales I made. There was also a lot of pressure from management and corporate to hit a certain sales number.

For the boutique’s customers, bras were a necessity, so getting people to walk in the door and buy a bra or two was not difficult. Our job as sales associates was to get people who came in for a bra or two to end up purchasing five bras, a set of pajamas, fragrance, a silk robe, and a negligee. C’mon, Ladies! Cross-sell! Upsell! Sell, Sell, Sell!

Approaching impressive, successful women generally decades older than I was and trying to sell them products that were very personal was quite the intimidating task for a 19-year-old (shy, unsure of herself) Krista. The other sales associates were more worldly “people people”—the type of people who can dish out compliments without sounding inauthentic, bond over small talk, and present themselves completely confidently.

I felt incredibly out of place and underqualified. To add on, my body type was not that of the store’s target customers, so I didn’t have a built-in understanding of the concerns of the people I was selling to.

At first, I tried to imitate the other sales associates. I would smile hugely, greet customers energetically, and try to be likable enough that they would buy from me. Frankly, I did a terrible job at this. Acting like an exuberant, all-knowing, arms pumping, bra-and-pajama motivational speaker was totally against my nature….so, yeah, I did not pull it off. More often than not, customers would respond with a tight-lipped laugh and furtive glance around for someone who could really understand them.

But every so often, a woman would wander in who I genuinely connected with. She was usually younger than typical customers and feeling both desperate for a bra that would fit her correctly and embarrassed to be in a store like our boutique. Feeling like you don’t belong but somehow you need to be there anyway? Now that I understood.

And because I instinctually got how she was feeling, I didn’t reach for my fake persona. Instead, I was myself. I inquired in gentle low-tones about her experience with finding a bra and offered careful suggestions for what product I thought would work and why. No upselling, no cross selling, no joke making. Rather, my “sales pitch” consisted almost entirely of listening.

Eventually, through quiet conversations, I would learn more things about her. Like that she was going to the beach in two weeks and couldn’t find a swimsuit that her in-laws wouldn’t find inappropriate. Or that her chest made it difficult to find comfortable things to sleep in that were more put-together than her husband’s t-shirt. And I would suggest solutions to her problems, which the boutique just happened to sell.

She would end up buying far more than the bra she came in for. But most importantly, she never felt like she was “sold” something.

My success with this type of customer gave me the confidence to apply my listen-first approach with every woman who walked in. And guess what? I started making sales that rivaled those of my colleagues.

It turns out that, yes, a bouncy personality or natural charisma can disarm customers enough to feel confident buying from you. But making your customers feel heard and understood works even better.

Not to mention, customers who buy from you because you offered an experience or a product that was tailored to exactly what they needed or wanted—after you listened to them—are far less likely to have post-purchase regrets and more likely to come back next time.

Now as I run my freelance copywriting business, I’ve continued to trust my listen-first approach when it comes to connecting with my own clients as well as helping my clients connect with their customers.

In practice, this looks like….

  • Interviewing and surveying customers about what they think about a product or service, instead of just assuming I know.
  • Couching every offer as a solution for a specific, real problem—instead of “just selling it.”
  • Never including a line of copy or a call to action that’s there just because everyone else has it. Instead, every line must be carefully chosen to meet customers where they are.
  • Prioritizing trust-building activities like creating helpful content, offering advice, sharing personal stories, and networking online and in-person, over pitching (for my business) or writing sales pages (for my clients).
  • Keeping communication clear and focused on customers, not on the company.
  • Perusing forums and online groups for what a target customer group really cares about.
  • Making sure my current clients feel taken care of and prioritized so that they know they are so much more to me than an invoice.

Not only are results better with a listen-first approach, but my clients and I also don’t ever get that “icky” feeling, like we just pushed a sale onto someone. We feel like the people we actually are, with a product or service that happens to be the perfect solution for our customers’ problem.

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