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Career
January 9, 2024

The Sky’s The Limit

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BEING NAMED THE FIRST BLACK HEAD of an airline in the aviation industry’s near-100-year history might be considered pressure enough. But how about taking on the role during a global health crisis that grounded countless flights and saw American carriers’ revenues plummet?

That was the challenge facing Brett J. Hart when he became president of United Airlines in May 2020, at the height of the COVID-19 pandemic. If all that wasn’t enough turbulence to handle, along with other senior leaders at one of the largest airlines in the country, he also forwent his salary.

Hart is well aware of the scrutiny he is under as he leads United in the post-coronavirus economy that disrupted the travel world about as much as any business sector. His is no small endeavor: more than 90,000 employees (with plans to hire 50,000 new people over the next several years) are involved in shuttling more than 800 United planes between some 324 destinations via the most comprehensive global route network among North American carriers.

“I recognize the moment and I understand the importance of the role that I have,” Hart says. “I also understand I can, in a way that I haven’t necessarily been able to in other times in my career, make a long-lasting impact if I do it the right way. And that’s what I intend.”

At the same time, he believes that while his opportunity is noteworthy, it’s way overdue. “We should shake our heads and say, ‘What in the world has taken so long—almost a hundred years to have a Black president in this industry?’ Far better and smarter people have come before me . . . people who dedicated their entire careers to [the industry], knew it inside-out and deserved to sit in this chair.”

Hart developed some of the sort of grit needed to take on the kind of a test he faces as a young man working construction for his contractor father back in Cassopolis, a small, rural community in southwest Michigan. “Every summer from age 12 until I graduated and left town,” Harts recalls. “I was neck-deep in it.”

And, he admits candidly, at the time he hated it. “It was tough, and he was tough.” Dad fired him four or five times, he says, adding with a chuckle that his father also gave him the nickname Part-Time. While he regrets now not wanting to soak up all he could about the industry—today “I have a belt with a few tools, but my wife won’t allow me to own much more than that; she has seen me at work”—he did absorb lessons about determination and diligence.

Taking a risk

Neither of Hart’s parents had more than a high school education, but they were both
entrepreneurial. “They were always exposing me to people and a lot of them seemed to be lawyers, whether it was in government or in business or just representing people. That was what I saw growing up and I knew I wanted to go to law school.”

He did so after majoring in English and philosophy at the University of Michigan, because “I knew it was going to be tough to get a job with those degrees.” Not that actually practicing law was top of mind; he wanted to be governor of his home state or in some other kind of public service. He just saw law providing lots of different career opportunities. “I wanted to have an impact.”

Earning his JD from the University of Chicago Law School, Hart did actually join a law firm on leaving school, but his career flight path took its first unorthodox turn after a few years. He took the position of special assistant to the general counsel at the U.S. Department of the Treasury in Washington, D.C., during the Clinton administration. Later he served as executive vice president and general counsel at Sara Lee Corporation.

Looking back, Hart sees these “risky” moves positioning and preparing him for United, which he joined in 2010. “Every step of the way, I have decided to paint outside the lines and take risks and take opportunities to learn new skills and take responsibility for things that ordinarily lawyers wouldn’t be responsible for and to move aggressively in directions that set me up to be considered to be something other than just your traditional lawyer,” he tells WayMaker Journal.

His groundbreaking (or should that be air-breaking?) 2020 appointment wasn’t the first time he stepped up to a big challenge at United. Joining the Chicago-headquartered airline as senior vice president, general counsel, Hart served in a number of roles, including six months as interim CEO in 2015 after incumbent Oscar Munoz recovered from a heart attack and subsequent heart transplant.

Not only did Hart step into the role of president at a time of economic challenge but a cultural shift soon followed, with businesses recognizing the need for a greater emphasis on environmental issues and diversity, equity and inclusion. United is involved in initiatives on all fronts.

Operationally, the airline has added new flights as more people have begun to travel again. Looking to the future, the company has invested $15 million in a company developing four-seater flying taxis, which it says, “have the potential to revolutionize the commuter experience in cities around the world.” Last December, the airline was the first to fly passengers on a plane using 100% sustainable aviation fuel.

With an eye on a different kind of green, United has awarded travel grants totaling over $500,000 to 51 golf teams at Historically Black Colleges and Universities (HBCUs) to help level the sport’s playing field. (United is the “Official Airline of the PGA TOUR.”) Separately, Hart was recently appointed to President Biden’s Board of Advisors on HBCUs.

At United’s Aviate Academy, the only flight school owned by a major commercial airline, the goal is to train some 5,000 new pilots by 2030—with at least half of them being women or people of color. United has also joined 60 other companies in the OneTen coalition of executives and companies committed to creating 1 million careers for Black talent without a four-year degree over the next 10 years.

Finding a sponsor

If Hart’s willingness to think outside the box led to doors of opportunity opening, he credits others with helping him learn how to walk through them well. He names Rick Palmore, now senior counsel at Den tons law firm in Chicago, as an influential mentor when he was starting out.

More than that, though, Palmore became a sponsor—“someone who was willing to put their credibility and the weight of their name and all that comes with that behind helping me advance my career,” Hart says appreciatively.

“I had the opportunity to watch how that brother operated… he was a lawyer, but what I noticed about him was he always thought about issues beyond just the law. He considered himself, I think even before anyone else did, a strategic participant in decisions that were being made.”

From Palmore, Hart learned about the importance of developing emotional intelligence: “Paying close attention to colleagues and understanding what motivates them, what moves them and how to get them to the right answer, how to make sure that I’m always relevant.”

From his experiences, Hart has some advice for those starting out in their careers who are looking for the same kind of help he received. “You have to have a bit of your story figured out,” he offers. “You have to know who you are and what it is, at least directionally, you want to accomplish.”

Many times, he observes, people seeking some sort of mentoring aren’t willing to open themselves up and “be a little bit vulnerable and allow people to understand who they are.” But that sort of human connection is an important element to the mentor/sponsor relationship.

“Sponsors are people who, for whatever reason, they make a connection with you, and they want to see you prosper. They want to see you do well, and they are willing to step in and put their own credibility on the line to support you, to vouch for you, to speak for you when that door is closed. You are almost never going to be in that room when the most critical decisions are being made about you, and that’s the time that a true sponsor steps up.”

But for them to be willing to do that, to put some of their credibility on the line for you, “there has to be something about you that connects them to you. And that would never happen with the sort of shallow connections that people tend to make.”

Making a plan

Those kind of meaningful business world relationships don’t just happen, Hart says. Keep in mind, too, that some of the most effective sponsors you have during your career may be people that you would never think would play that role. “You may have nothing in common with them,” says Hart. “They most likely won’t be Black, in some instances, but when you open yourself up and you work on those relationships, they will present themselves. But you have to be willing to work to make them happen.”

Becoming comfortable standing out has been a process; he didn’t start out bringing his full “authentic self” to the table. “Particularly as Black men, you’re trying to figure out exactly how we’re supposed to walk and talk in that environment, how we are supposed to carry ourselves,” he says. “We almost never get the benefit of the doubt… so we bring all of that to the office on the first day and we carry it.”

It is only over the last five to 10 years that he has realized more fully “the special element that we bring to these roles. And it’s wholly possible to be your authentic self and to have that added value in any corporate environment.” He adds, “The sooner we can all realize that in our career, then we can sort of uncork that extra value that we bring to the table that no one else can bring, because they don’t have the experiences that we bring to the table.”

“You have to be willing to step up and seize the opportunity when it presents itself.”

Knowing a thing or two about the importance of a clear flight plan, Hart has two pieces of advice for those looking to get ahead in corporate America. The first, naturally, is that you need to know where you are going. “I’m not talking about a rigid plan,” he clarifies. “I’m not saying you set one goal and you do whatever you have to do to get to that goal.”

He’s talking about having a three-or five-year target in mind, along with the interim steps you will need to take along the way. “And then accept in the back of your mind that almost none of those plans work out exactly the way that you set them out on paper,” he adds. “But it’s the discipline of having it, it’s the order of going about pursuing what you’re interested in and what you want to accomplish that then gives you the flexibility to rework that plan as life happens… and opportunities present themselves when you least expect them.”

Hart has never had one of his plans work out quite the way it was supposed to, or an opportunity present itself exactly when he wanted, “but there’s value in having [a plan], in controlling, in that respect, your own destiny.”

Along with planning, you need pluck. “You have to be willing to take risks,” he says. “You have to understand the potential outcomes.” That doesn’t mean you throw caution to the wind, “but it means that you have to be willing to step up and seize the opportunity when it pres- ents itself. And you have to be able to appreciate the potential upside of the opportunity and the downside.”

Hart references the saying that you miss 100% of the shots you don’t take. “And it’s absolutely true, and it’s absolutely true in corporate America as well.”

For all his high-flying, trailblazing role means, Hart is happily grounded by his family: he and his wife, Dontrey, a lifestyle blogger and philanthropist, live on Chicago’s South Side with their three sons.

This article was originally published in the Spring 2023 issue of WayMaker Journal.

“If I walked out of United Airlines tomorrow, I promise you that the airplanes would keep flying,” Hart says. “The lights would stay on. They will talk about the fact that I was there at some point, but my real impact in life is with those three young men that I’m trying to raise and teach how to be good strong brothers, and to make their way in this world and make their contribution to our community over the course of their life.”

BRETT J. HART: MY WAYMAKERS

The business community here in Chicago… [those] that have been most critical in my career. When I became acting CEO, people came out of the woodwork to say, “Hey, here’s what you ought to be thinking about. I’m here. I’m available at all times.” People who I had just read about were willing to step up and say, “I’m here for you. I’m proud of you. I want you to be successful. Here are three things I want you to think about, here are three people I want you to call.” The brotherhood that exists here is just really special… [people] who just genuinely want to see a Black dude be successful in a role like this and understand the importance of it for the broader community. And for that, I’ve been grateful.

From an interview with Louis Carr

This article was originally published in the Spring 2023 issue of WayMaker Journal.