Listen to some people, and you might be forgiven for thinking that being successful is a bit of a walk in the park—do what you love, play to your strengths and so on, no sweat. Ron Williams has a slightly different view: he advocates facing your weaknesses and looking for the risky opportunities—going out on a limb.
It’s an approach that has paid dividends. From washing cars as a young man, Williams has risen to prominence as a widely admired business leader with a particular gift as a turnaround specialist. By way of example: when he joined health insurance giant Aetna Inc. in 2001, the company had losses of almost $300 million. A decade later, when he stepped down as chairman, Aetna’s full-year operating earnings were $2 billion.
That transformation saw the company named Fortune magazine’s most admired company in health care for three consecutive years. In December, he was included in the Forbes Healthcare Summit’s list of Top 10 Leaders of the Decade for “helping future leaders with strategy, values-based leadership and the continued transformation of the health care industry.”
A member of President Obama’s President’s Management Advisory Board from 2011 to 2017, Williams continues to share his wisdom through his RW2 Enterprises leadership consultancy. He also serves on several major boards.
Those C-suite chairs are a long way from the back seat of the car he was cleaning when he decided he needed to take some serious steps to change the direction of his life.
Growing up on Chicago’s South Side—Mom was a manicurist; Dad was a bus driver—he didn’t know anyone who had gone to college. Working from a young age, he didn’t have time for sports, “so for me, my aspirations were absolutely so minimal. I just knew what I didn’t want to do.”
And that was spend forever in his afterschool and weekends gig at a carwash. “Summer, winter, fall, you name it… and that made me clearly understand that I did not want to spend my life in that environment.”
He recalls one winter day when the owner was pumped that they had washed 350 cars. “Now this was Chicago in the dead of winter,” he says. “There was slush and salt and snow. My job was to vacuum the car out—climb in the back seat, clean the back windshield, ride through the carwash line and when the car ended get out and wipe down all that water.
“It was cold as hell out there, and I said to myself, ‘I don’t know what I want to do, but I sure as hell am not going to do this for the rest of my life.’ And that was a moment at which I began to say that there had to be a better future. And I set about trying to figure out what that was.”
Those betterment steps included education—he would go on to get a bachelor’s degree from Roosevelt University and a master’s degree in management from the Massachusetts Institute of Technology’s Sloan School of Management. Then there was application of what he was learning.
While many people transition from the corporate world to entrepreneurism, Williams went the other way. “The first business I started failed miserably, and what I learned was I was a very good salesman, but I didn’t know anything about how to run a business,” he says. “And I said to myself, ‘Where will I learn to actually run a business?’ And so, I took my good salesman capability and I joined a computer company.
“Not only did they hire me to sell, which I was doing, it was a place where I learned how to read a financial statement, how I learned how to plan budgets, how I learned all the functions necessary to run a business.”
After several years there he took what he had learned and started another business. “I applied all of those capabilities to that business, and that was successful,” he says. “You know, one of the things people don’t understand is you fail your way to success. Failure is the progressive elimination of what won’t get you there. So, then you move on to the next thing, and finally you get to the point where you know how to do what you want to do. So, a large company is a great training ground.”
Williams is not only big on learning what you don’t know, but also learning things you may not think you need right now.
“I want to learn everything I possibly can just to know about it or to be smart,” he explains. “The biggest mistake that people make is they think they work for someone else. They work for themselves, and the single most important thing you can do is to make yourself more valuable. There is no better asset you have economically than making yourself more valuable, knowing more and putting yourself in a place where you bring more to the party and can get paid more for doing it.
“I often hear young people say, ‘They’re not paying me to do that.’ No, they’re not. And they never will. Once you do it and you learn how to do it good, you can go to the next person and get paid for doing it.”
Williams has a personal rule: every year, be 15% better. “It’s very simple to convince yourself you can be 3-4% better, but if you’ve got to be 15% better next year, you’ve got to think really deeply about what you need to learn, what you need to know and how are you going to get there.
“And if you do that, you’ll wake up in four or five years and you’re going to know a lot more. You’re going to be more valuable and you’re going to have an opportunity.”
Williams took on the challenge at Aetna after a successful season as a company president when he realized the CEO spot wasn’t going to open up for him. “I could have stayed there, been comfortable, had a good living, but I figured I could be a CEO,” he says.
Making the move was fueled by his belief that you shouldn’t get too comfortable. His advice for those who want to keep stretching and growing like he did—look for people to help you.
“When I had an idea that, Gee, maybe I’d like to try sales, I found people to talk to. Sometimes I’d see them in a store. Sometimes I’d see them on the street. ‘I see you sell for a living. Tell me about that. How did you get that job?’”
When you reach out like that you generally find people are willing to help because “they didn’t get where they were on their own.” But you have to be intentional: often after speaking somewhere, around 25 people will come up to him and ask for his business card, he says, but only one will actually follow up and reach out for help later.
“I have some people who called me; I’ve talked to them when they were in undergraduate, getting their bachelor’s. I’ve talked to them when they were a graduate. I talked to them when they entered the business world and I’ve been really mentoring them and helping them, but it all started because they reached out and asked for help and said, ‘How do I get from where I am up to where I want to go?’” Developing that kind of attitude required what he calls a reframing. “We all grow up with a script in our head and sometimes it’s from our parents, sometimes it’s from the neighborhood, sometimes it’s from TV. And sometimes it’s parts of other societies that don’t value who you are and what you can become. Reframing is simply not accepting other people’s view of who you are and what you can accomplish.”
He gives the example of someone being told they are no good at math and never will be. “‘You won’t be good in business,’ or ‘You can’t sell. You can’t do this. You can’t do that.’ I can tell you people can learn to do anything. All those people who are doctors, lawyers, dentists, accountants; they weren’t born that way.’ Reframing is giving yourself the latitude and the flexibility to say, ‘I don’t have to accept the box I’m in. I can take that box apart and I can move into a much bigger space.’”
Williams credits part of his success to willingness to take on clear challenges. “I wanted to be where the action was. And what I learned was that when you had a sales goal of $1 million and you deliver $1.1 million, there is no refuting that you are a star performer.
“Now, when you’re doing things that are softer, where the results aren’t really visible, there’s much more subjectivity about your performance. And so, I always liked to pick things where the goal post was clear and overachieving was clearly going to result in distinguishing yourself.”
Many call that high-risk, but he disagrees. “One of the things I’ve learned is the greatest risk in life people take is not taking a risk. Because by and large, if you take a job that’s risky in that context and it doesn’t work out and you can always go do something different—get a job just like you would have gotten if you hadn’t taken that risk.
“It’s really important to focus on opportunities where there are clear results. It’s also important to focus on opportunities that are broken, because I can tell you, when a company is broken and they’re struggling, they don’t care if you’re from Mars. They don’t care if you’re green. If you can help them achieve their business goals, they’ll hire you and you will learn a lot more in that situation.”
Another factor Williams identifies in his rise to the top: the support of his wife, Cynthia. “When you take on an assignment or a job, you’ve volunteered,” he says. “Your partner’s drafted. That’s fundamentally important to understand.”
Remember, there’s a big difference between the two. “It’s your dream. It’s your vision, it’s what you’re doing… you have to have real conversations about the obligations of leadership. You know, people think about the rewards, the money, the parking space, the bonus, the prestige. They don’t think a lot about the obligations they take on.
“When you take on the obligation to be responsible for 50,000 people, they don’t go to fancy meetings. They don’t go on private planes. They’re counting on you to make the right decisions to keep them employed. And I think it’s that mutual obligation between you, your spouse, your partner, and an understanding that if you’ve gotten to that level, it’s bigger than you.”
He finishes this line of thought deadpan: “I always tell people, it always starts with really understanding that the answer is always, ‘Yes, dear.’”
Williams’ success has opened doors to influential board membership (American Express, The Boeing Company and Johnson & Johnson), an opportunity still denied many Black executives. Those seats are important, he believes because “you want to be in the room where it happens, and you want your views, your opinions, your perspective, which is different than everybody else in that room, heard and felt.”
He recommends serving on a nonprofit board to get some experience and exposure—his first was with a local YMCA while working in California. “I watched senior executives who were on that board. I saw how they conducted themselves. I saw how they ran committee meetings. I saw the process of governance.”
Starting small not only provides learning opportunities, it also helps you become known as a leader in the local business community and “gives people a reason to, to ask you to join because you can contribute to their business success.”
Williams has shared some of his wisdom in Learning to Lead: The Journey to Leading Yourself, Leading Others, and Leading an Organization, published in 2019. It has been described as “a gift to the next generation of American leaders,” by Steve Forbes, Chairman of Forbes Media, who calls the author “a classic American success story.”
In an online review, one former public company CEO, said he wished the book had been available at the beginning of his time on the job, praising its “counterintuitive, but compelling, insights.” Another reader applauded it for its “calm, thoughtful approaches to any business challenge.”
What’s one piece of advice he wishes he’d been given earlier in life? “Understand finances,” he answers. “We don’t pay enough attention to our own financial well-being early enough. We don’t pay enough attention to our own legitimate aspirations.
“Wanting it’s not enough; you have got to plot the course to get to it. Now, the course is never a straight line and I wish somebody had said, ‘You’ve got to understand, you may go this way and this way and this way and this way, but ultimately you’ll get to where you want to go.’”
He underscores the need to improve yourself, the need to develop financial skills and the need to take risks. “If you do all those things, you are going to have a better life than you would have had,” he says. “Whether you will be CEO one day, who knows, but the No. 1 thing is, if you can start out in the back seat of that car and end up anywhere along the path, you’re going to be a pretty happy person.”
The important thing is that, wherever you end up, you are in the driving seat.