indicatorSales and Marketing

Choose empathy: Top sales expert Kim Orlesky’s advice for transforming your sales

By ATB Financial 29 November 2018 5 min read

Empathy may not be the first word you think of when you hear “sales.” It certainly wasn’t for Female Entrepreneur of 2017 and leading sales coach Kim Orlesky when she sat down with her business coach years ago. So when she was told that to boost her sales—and save her business—she needed to connect with her audience more, she didn’t believe it.

“At the time, I thought it was ridiculous!” admits Kim. “That’s not what they taught in corporate sales.” And Kim is no stranger to corporate sales. She’s held prominent sales roles in Fortune 500 companies like Xerox and American Express for almost a decade. But she craved something more.


Adventure—and personal discovery—awaits

This craving launched her into life changing action: quitting her impressive job, and traveling the world solo—she covered 17 countries in six months, and wrote two books as a result.

Along the way, Kim found herself being challenged in ways she never had—the way only travel could.

“Before travel, I was a super ‘Type A’,” Kim reveals. “I needed to have my entire life in a spreadsheet. Travel forced me to be a lot more fluid for the things that come and be open to opportunities that I couldn’t have predicted. This helped a ton in business, because we can’t predict everything, so why get stressed out?”

“I’m also much more transparent and honest about my personal struggles,” shares Kim. “It’s okay to not wear a brave face, to say I’m in trouble, or I don’t know how I’m going to get through. Whatever will come will be the right answer for that moment.”


Coming full circle...almost

It was when she came back from her global travels that she realized how much she actually did love sales. “I wanted to change the conversation to help others love it too. For so long, sales has been this old, white man’s game—there’s zero diversity in the conversation.” She recounts that the one time she saw a woman appear on the top 10 sales book list, the title was something to the effect of Hypnotise your Client into Buying. Yikes.

So she set out to become a thought leader in the industry, starting with writing and public speaking, and leading into an online course. And once she took her business coach’s advice—she included more stories, explained the “why” behind the “what”—she saw her sales cycles happening faster.


Building an empathy-driven entrepreneurship empire

Now, she’s President of KO Advantage Group, where her and her team focus on training other businesses on how to have a high value sales conversation that all starts with empathy.

“When we bring on a client, they should be a client for life,” insists Kim, “even if they’re purchasing a one time thing. And we treat our prospects as if they’re already our clients. When people feel like they’re already part of something special, they’re more likely to get onboard.”

“We help as much as we can. We genuinely want to see every entrepreneur become a revenue generating machine.” As she and her team interact with their clients, they come from a place of equality. They’re adamant in communicating that “we feel this with you—we’re not better than.”​

“When we communicate our sales process in that way, we show our clients that they can do the same with their clients.”

“One of our modules [in our online course] is just on empathy and storytelling, to enhance connection and sales,” explains Kim. And—flying in the face of gender stereotypes—60% of the students are men.

“Empathy isn’t just a female conversation,” she adds. “Everyone wants to feel more connected to their customers. And when we feel more connection with them, we don’t need as many customers.”


Let’s change our minds about sales

Kim Orlesky suggests building trust and empathy with your customers.

To adopt this sales philosophy for ourselves, it requires some intentional mindset shifts.

“Sales is not the act of doing to somebody,” Kim says. “We forget this all the time! We think it’s pushy, when it’s not! Sales is education, relationship, connecting with people—getting to understand them first and foremost.”

Kim often relates a sales relationship to a dating relationship—which brings a different perspective coupled with startling clarity.

“With any relationship, if it’s really hard to get people to open up, then it’s probably not the right relationship,” she says. “I mean, if someone didn’t share their goals and aspirations, you wouldn’t keep dating them! Same with sales relationships—these are clients for life, so there needs to be trust and transparency!”

For Kim, here’s what sales ultimately boils down to:

“We’re not convincing people—we’re coming alongside people.”


Practical tips on how to grow your empathy


Ask better questions.


Sales is understanding your client better, not telling your client what they want,” Kim points out. “When you get answers to their questions, use that information to help them become better version of themselves and their business. Sales is being genuinely interested in them.” Ask loaded questions.


“Find out what your client wants to achieve, and how they’ll feel when they achieve it.” Kim encourages us to “tap into something greater than the tangible—you’re helping them create an ideal state through product or service.”


​One-liner advice for all kinds of entrepreneurs
For those wanting to start their own online course:

“Sell it first, then create it—it’s a lot easier to create it when people want it.”


For those wanting to become a speaker/host workshops:

“Sell the idea first, then create it.”


For aspiring authors:

“Be okay with being vulnerable.”


For anyone going through a hard season of life:

“This too shall pass.”



Do you want to learn from successful entrepreneurs like Kim? The ATB Entrepreneur Centres are always working with incredible Albertans like Kim to host helpful workshops. Take a look to see what's happening at an Entrepreneur Centre in your community.​

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