- Naomi Wheeless leads a team of more than 1,000 employees at Square.
- When working her way up, she learned a few crucial pieces of advice about leadership.
- For Wheeless, it’s important to balance work and fun, make time for others, and speak up.
This article is part of a series called “Leaders by Day,” which takes a look at how prominent business leaders are tackling various challenges in today’s economy.
Naomi Wheeless first started working in customer relations when she was in college. She was working in a contact center making $12 an hour.
Wheeless eventually worked her way up to directing the call centers at companies like Satellite AutoGlass and Bank of America. She earned an MBA, and served as vice president of operations at Capital One.
Today, Wheeless is the global head of customer success at financial services and technology company Square and serves on the board of ticketing company Eventbrite. She manages Square’s largest team, which comprises 1,000 employees across 10 countries.
Throughout her career, she’s often been the only Black woman at the table. And she’s learned a lot about leadership, especially as she’s navigated the often predominantly white and male tech industry.
“It’s very, very common that I’m the only minority in the room, one of very few women in the room, and often also likely the youngest in the room,” Wheeless told Insider.
Here are the most important leadership lessons Wheeless has learned throughout nearly two decades of building a career.
Finding a balance between work and fun
Wheeless has high expectations, but she also realizes the importance of being able to form lighthearted connections with her team.
“One of the things that I realized early on is that I’m very good at demanding a lot, having super high expectations, and making sure my team feels incredibly rewarded along the way and that we have a lot of fun,” Wheeless said.
Wheeless said that leaders who are too preoccupied with being likable can end up being less effective. On the other hand, though, nobody wants to work for an overly intimidating boss.
That’s why she makes a point to keep her interactions with her teams lighthearted and let her personality come through, as well as recognize her employees for their hard work. At the same time, she’ll also be upfront when an employee is missing the mark.
“Figuring out what’s the right balance,” Wheeless said, “where you have the respect and admiration and can really drive forward impressive results through the work of others, but have fun on the way, and a lot of people really want to come work for you — that’s how you know that you’re doing a good job as a leader.”
Making time for others
Making the time to speak individually with the team is crucial for Wheeless.
“I will set up a one-on-one with anybody from the janitor to the CEO,” she said. “I don’t care who you are, what team you’re on. If you want to talk to me, you should get that opportunity.”
She takes efforts to make herself open and approachable to everyone. Before the pandemic, Wheeless never used an office. Instead, she would be out on the floor greeting her team and mingling with employees.
That’s difficult to re-create as work has gone remote. But even still, Wheeless prioritizes one-on-one meetings over business meetings when she gets requests to chat, and makes efforts to help spur on the improvement of her employees.
“One of the things that I love about leadership is the fact that it doesn’t really matter how great of a leader you are yourself, if only you are great,” Wheeless said. “The true testament to your success is how good of a job you do at bringing out the best in others.”
That starts with making time for them.
Calling out microaggressions
Giving advice and helping others to succeed is a large part of Wheeless’ role. But she also makes sure to look out for herself, and keeps others accountable when she knows she’s encountering microaggressions at work.
Microaggressions refer to subtle forms of behavior that discriminate against a marginalized group — for example, neglecting to listen to a woman’s advice at a meeting, but praising that same advice when it comes from a man.
“I’m a very firm believer that it’s not the responsibility of the minority to overly prove themselves at all times,” Wheeless said.
She’ll call out these kinds of behavior on the spot, or at least make a point to pull a person aside and make them aware of their behavior.
“When those little microaggressions show their head, I make sure that I provide feedback, usually right there in the moment, in a very professional and tactful way.”
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