Early Returns: What Job Best Prepared You to Be a Company Leader?

By Brian O'Connell June 15, 2021
Early Returns: What Job Best Prepared You to Be a Company Leader?

​Michael Bloomberg started out as a parking lot attendant. Jeff Bezos flipped burgers at McDonald's. Oprah Winfrey was a grocery store cashier.

They are just a few of the business icons who started out with humble beginnings, then turned their first jobs into stepping-stones toward astronomical success.

Many CEOs and business owners say it was those "seed planting" jobs they held as teenagers or 20-somethings that set the stage for long-term leadership growth.

What jobs best prepared today's executives to become leaders in their fields?

For Steve Wardlaw, executive chairman at Emerald Life, an insurance provider in London, the path to leading a company that caters to underserviced community members started at a major children's retailer. That's where he first learned that customer care was key.

"My first real job was in customer service in Toys "R" Us," Wardlaw said. "That meant dealing with both easy and hard customers."

It also meant dealing with a penny-pinching management culture.

"Although I wasn't allowed, there were times when I stepped outside the rules on returns and refunds," he said. "Occasionally, I caught flak, but circumventing the rules taught me about empowering more junior staff."

The experience led Wardlaw to significantly alter his company's definition of customer service when he became CEO.

"We don't give our call center representatives a script," he said. "Instead, we train them on what they need to do, how to interact and how to do the little things that keep customers coming back, like helping customers with a small discount or sharing a useful link to solve a problem online. We also don't time our call center agents, because great customer service, to us, means keeping calls short."

Learning from Tough Taskmasters

Some corporate executives learned what not to do by watching their early managers.

"When I was in college, I took up a job as a server in a sushi restaurant, and it has been the most enlightening workplace experience that I have ever had," said Matthew Paxton, founder of Hypernia, a gaming review platform based in Richmond, Va. "Our manager was cold and a hardcore perfectionist. It was tough working for him. Everyone had to walk on eggshells around him, and you were expected to work even when you were sick. As a result, employees often didn't last long under his management and those who stayed would often dread coming to work."

The experience made Paxton a more empathetic company leader at Hypernia.

"The restaurant job made me realize that to be a good leader, you must strive to understand your employees' situation and make their mental and physical well-being a top priority," he said. "Despite the tough times, I wouldn't trade that experience for anything, as it helped shape me as a businessman and business owner."

Age Is Just a Number

For Kate Williams, CEO and owner of People First Content, a digital content agency in Broken Arrow, Okla., working at a coffee bar taught her early on that age wasn't a barrier to career advancement.

"I worked as a barista at the Nordstrom espresso bar all through college," Williams said. "The company created an exceptional working environment, and I was able to go through training and eventually become the department manager when I graduated. I was responsible for hiring, firing and training a team at the ripe age of 21."

Williams said that having so much workplace responsibility right out of the gate ended up being a big career advantage.

"It taught me that age is just a number when it comes to leadership," she said. "I learned that if you find talent, [you should] nurture it. I also learned that investing in training is critical, as is giving people room to grow and become leaders."

The barista post also taught Williams that good companies breed long-term customers.

"Even though I no longer work for the company, I am a Nordstrom customer for life because of how well they treated all of their employees," she said. "The lessons I learned there about how to grow sales, keep customers happy and build a team helped me succeed in my current career as the owner and founder at People First."

Elements of a Good CEO

What are the signs of an early career professional who is CEO material?

Patience, empathy and an eye for good customer service certainly help. But that's not all. A young worker's emerging story counts, too.

"In my early days, I was always in between jobs," said Dominique Kemps, founder at GlassExpertsFL in Miami. "However, the one experience that changed my mindset and pushed me to succeed in business was a grocery attendant job."

Kemps was a department head and had employees report back to her at the end of the day. "I took note of records and managed the store," she said. "There, I learned a lot about becoming a leader. I made a few mistakes during the job, but the lessons I learned made up for it."

It was at the grocery store where Kemps first embraced the two leadership traits that all good CEOs should have:

Dependability. "You need to be bankable or dependable," Kemps said. "Can we trust you to have a job delivered on time and with excellence? Starting out, I remember determining that I'll be as dependable as possible. Consequently, all young workers with a career path should train themselves to be trustworthy and dependable. Ideally, you'll have a boss who can help you do that."

Communication Skills. Learn how to communicate with people around you and pass good information. "As a CEO, it'll be expected of you always to have good communication skills," she added.

Lessons You'd Tell Your Younger Self

CEOs who now run their own show have a lot they would want to say to their younger selves just starting out. Having patience, it seems, is near the top of that list.

"Everything takes so much time, and that's a lesson best learned early," said Jennifer Harder, chief executive officer at Jennifer Harder Brokerage, a mortgage services company in Vancouver, British Columbia, Canada. "Everything takes longer than you'd want, whether it's closing a client, building a plan, adding team members, or anything else related to your business. Regrettably, the rest of the world does not operate according to your schedule."

Accomplishing those big goals takes patience and a dose of creativity. "This is why it's so critical for a CEO to sow as many seeds as possible, especially in gathering clients," Harder said. "This way, you're not entirely dependent on a single solution to succeed."

Harder would also tell her younger self that delayed gratification is a necessary attribute for any entrepreneur. "Anything worthwhile is not easy," she said. "Many people who are unable to persist will give up. Recognizing that success may take several years can help you stay in the game."

Not taking life too seriously—even in the corner office—is also a message that corporate executives wish they'd embraced back in the day.

"If I could go back in time, I'd tell myself to relax and enjoy the ride," said Dennis Hancock, CEO of Mountain Valley MD, a Canada-based biotech firm. "When we're young, we get so caught up in worrying about where our career is going that we forget to enjoy where we are at the moment."

Brian O'Connell is a freelance writer based in Bucks County, Pa. A former Wall Street trader, he is the author of the books CNBC Creating Wealth, (John Wiley & Sons, Inc., 2001) and The Career Survival Guide, (McGraw-Hill, 2004).



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