16 Successful CEOs and How They Got There

It takes doing the right things at the right times to be one of the most successful CEOs of all time. But even with talent and resources at their disposal, the good can fail to make it to great simply because they missed an opportunity or zigged when they should have zagged.

The great CEOs overcome obstacles to become great — but how did they do it? We know it takes talent, hard work and courage to forge a career path and become a successful CEO. But what else does it take? Let’s look to some of the most successful CEOs of our time to find out what unique practices and beliefs they bring to the role.

Mary Barra, General Motors

Conversations. Many, many conversations

Mary Barra is frequently listed as one of the most successful CEOs. In addition to her high-profile role as the only female CEO in her industry, she is also the highest-paid CEO of the “Detroit 3” automobile manufacturers. She strives for an open culture, including frequently asking her staff for feedback on specific and more general activities of the organization. She suggests leaders consistently ask their team members “What’s your opinion?” and in fact, she led efforts to change the company culture to a culture of feedback that allowed for workers to speak up when they noticed problems rather than sweeping them under the rug. She believes meetings are for discussion and that information dissemination should happen before these sessions so that time is better spent determining options and making decisions.

Ms. Barra thoroughly understands the importance of leadership and mentoring, and she encourages her team to find mentors everywhere around them, as she does. She believes people can benefit from formal mentorships as well as day-to-day interactions with the smart people around them. She values those conversations as a way to improve her own decision-making and help other people do their best as well.

Jeff Bezos, Amazon

Differing opinions

Amazon CEO Jeff Bezos knows he doesn’t have all the answers all the time. In fact, he firmly believes that really smart people, those who make great business decisions, are those who are willing to change their minds and are willing to do it often and quickly. He argues that those who are “right a lot” are the same ones who can state an opinion one day and share a polar opposite perspective the next. They keep thinking about an issue, teasing it out, thinking it through from another perspective to figure out if they’ve missed something important. And if they have, they own it, quickly and decisively. They change their answer, and they do it publicly.

He describes those who are “wrong a lot” as those who only pay attention to the facts and details that support their original opinion. They fail to look at the situation from different angles or listen to others’ perspectives. They deeply fear criticism and are so afraid to be wrong they fail to consider any suggestions that don’t align with their own.

Bezos created a mentor program which allows an executive to effectively shadow him for 1-2 years, providing tremendous mentorship opportunities in their time with him but also giving Bezos full-time access to a talented individual empowered to share opinions openly and honestly. This role is designed to give him valuable insights from a trusted executive who can help him take action on his plans but also challenge his thinking on key points as necessary.

Warren Buffett, Berkshire Hathaway

Ethics and perspective

Warren Buffett leads with ethics and an eye toward long-term results. He builds security into his strategies to allow his team to do their jobs without undue market influences. Because they’re able to ignore the day-to-day turbulence of finance, their efforts ultimately maintain solid results. 

He also believes that his obligations to his investors include not taking undue risks with their funds. His returns are steady without being scary. Investors and employees know they can count on him to lead the organization as if every dollar was his own. 

This doesn’t mean he’s infallible, of course. He personally takes responsibility for the loss of several billion dollars of Berkshire Hathaway’s funds due to a poorly timed investment in gas and oil, but his overall fiscal responsibility allowed the organization and the shareholders to weather that storm and the accompanying dip in stock price.

But how did Buffet gain so much wisdom around investing? Was he a natural-born investor? Of course not! He read books about investing from the time he was a very young man, buying his first stocks at age 11. 

As he studied business as an undergraduate, he modeled his investing strategies around Benjamin Graham’s concept of value investing, eventually choosing his graduate school program at Columbia in part because Graham taught there. He would later go into business with Graham, allowing him to continually learn from his mentor as he diversified and grew his investments over time. Buffett parlayed his mentor’s investment strategies into a portfolio, making him one of the richest people and most successful CEOs in the world.

Ursula Burns, Xerox (former)

Grit

Ursula Burns was told early and often that she had three strikes against her: she was black, she was a girl, and she was poor. 

Instead of backing away from challenges, she entered into the predominantly-white-male field of engineering. And when she realized she hated chemical engineering, rather than quitting altogether, she tried mechanical engineering, which she loved. 

She took many risks, including accepting an internship far away from home and taking multiple challenging steps up the corporate ladder. She even led Xerox through an acquisition to move from a copy and printing company with shrinking markets in a digital age to a technology and services enterprise, with a virtually infinite market. 

Burns’s willingness to persevere in these challenging situations and her success in leading Xerox through an organizational transformation has earned her tremendous respect in the business leadership sphere.

Charles Butt, HEB

Caring

Charles Butt heads HEB, a privately held supermarket chain operating out of Texas that many Texans are passionate about. With more than $25B in annual revenue, it’s one of the largest retailers in the US. 

Interestingly, Butt is better known for his charitable giving than for his role at HEB, yet his employees give him a 99% approval rating. Philanthropy is built into the organization’s DNA, with 5% of pre-tax profits going to charity. Personally, he has given millions for education and Hurricane Harvey relief, and he has committed to giving away half of his $10B-plus portfolio to further fund education efforts. 

Day in and day out, however, he understands the challenge specific to the service industries wherein locations must be staffed for long hours, but much of your workforce is part-time and/or has other major commitments such as school, family, or another job. Scheduling around odd hours and requirements can be daunting, but Butt has woven it into the fabric of his organization, which becomes apparent when employees talk about their experience working for HEB. Employee after employee talks about being given the flexibility they need for life and being treated well and with respect by their managers. That leadership comes from the top.

Jack Dorsey, Twitter and Square

Delegating decisions

Jack Dorsey believes in leadership that asks each team member to make their own decisions. He wants outcomes determined by people best positioned to understand the impact of those actions, and he sees his role simply as the leader to move the team in the general strategic direction. 

Interestingly, he sees any situation where he has to make a decision as a sign of organizational failure. This strategy allows the organization to succeed on the team’s collective strength rather than relying heavily on one person at the top.

Bill Gates, Microsoft (former)

Life outside work

While Bill Gates firmly believes that businesses, especially new ones, can require periods of intense sacrifice to accomplish their goals, he knows that in order to stay successful in business, one needs to have interests that take them away from their work and allow them to clear their minds and reset. 

His hobbies range from athletic to intellectual, including tennis, Bridge (with his leadership mentor Warren Buffett, no less), reading, travel, and family games of Settlers of Catan. He expects to read a book a week and many more when on vacation, and he knows that along with reading, exercising and playing games all work together to keep you fit, energetic, and sharp.    

Gates understands that setting boundaries around your time and being willing to say no can be critical to both efficiency and attitude. By stepping away, he allows himself the opportunity to refresh and unplug so that he’s happier and able to do his best work.   

Pat Gelsinger, VMware

Balance and accountability

For Pat Gelsinger, faith and family are very important, and he’s careful to ensure that work doesn’t take over his life. He has a mission statement based on prioritizing God and family while also working hard, and he takes seriously his commitment to do all three of those things. 

Acknowledging the difficulty of keeping those competing demands in balance, Gelsinger looks to mentorship for help. He holds regular meetings with his mentor(s) in order to stay on track, and he mentors others as well to help them achieve their goals. 

Manny Maceda, Bain & Company

Understanding the workforce

Bain & Company has made Glass Door’s list of “Best Places to Work” 11 years running, including filling the top spot in 2012, 2014, 2017, and 2019. 

When faced with the challenge of engaging the younger workforce while tapping into the historical knowledge and existing experience within the organization, Manny Maceda decided the answer was not to choose between them but rather to provide options for both. Rather than doing business as usual — where hierarchy is largely determined by age — or trying to shift everyone’s thinking to value the things millennials do, he’s pushing flexibility within the organization.

By adding programs designed to appeal to millennials without taking away the consistency that more experienced workers typically value, Maceda is making the workplace appealing to a broader range of workers. And with programs such as pro bono consulting, he’s able to capture the hearts of not only his millennial employees but also other workers who are now able to bring their personal causes into their work life. 

Further, he’s providing opportunity based on achievements and ideas rather than allowing under performers to linger in high-ranking positions based on seniority or experience.

Sylvia Metayer, Corporate Services Worldwide at Sodexo

Collaboration & innovation

Sylvia Metayer’s efforts at Sodexo are all about helping people thrive at work. 

She has guided her team through a process to discover how they can help their clients build positive, productive cultures, and she takes seriously her responsibility to apply that lesson in her own organization. She has focused a great deal on career paths and opportunities, evolving the organization from a more traditional authoritarian model to a flatter, more collaborative environment.

In her efforts to lead culture change in the organization, she and her team have made everything about accountability, pushing decisions from the executive team to others within the organization and even assigning tasks to other teams in order to move more quickly. 

This expectation of accountability and ownership has fostered innovation, as it allows those at various levels of the organization, especially those on the front lines, to find opportunities for improvement and make it happen.

Beth Mooney, KeyCorp

Up for a challenge

As the only female CEO of a top 20 bank in the US and one of Fortune’s Most Powerful Women in Business, Beth Mooney isn’t afraid to take a risk. 

In an interview with Fortune, Mooney talked about her climb to the CEO role of KeyCorp, starting with the only job she could originally get in banking, as a secretary at First National Bank in Houston, TX. “I never said ‘no’ to a challenge. I never said ‘no’ to an opportunity. 

“Have enough confidence in your own ability and your ability to work hard and make good decisions and go into the unknown. And I think you will learn more than you’ll ever imagine you can learn and you build confidence by accepting those challenges versus hanging back and saying ‘I’m not ready’ or ‘I don’t want to do that.’”

Satya Nadella, Microsoft

A willingness to set a new course

Satya Nadella faced a unique challenge when he took over at Microsoft, as few business leaders in recent history are more well-known than former Microsoft CEO Bill Gates, whose name is still synonymous with Microsoft almost 20 years after stepping down as CEO. 

So, when Nadella took over following Steve Ballmer’s mix of successes and missteps, it took a tremendous amount of vision to move beyond Gates’ mission of “a PC on every desk and in every home, running Microsoft software” to the more enduring goal to “empower every person and every organization on the planet to achieve more.” He also broke away from Microsoft’s historically anti-Linux stance to embrace the operating system, even becoming a Platinum member of the Linux Foundation. Further, he sought to broaden Microsoft’s offerings via several high-profile acquisitions, such as LinkedIn, GitHub, and Mojang, which created Minecraft. While it’s relatively obvious, at least in hindsight, that Microsoft had to break away from Gates’ legacy in order to survive, Nadella had to have confidence in his own vision and a willingness to lead the team in new, exciting directions.

Larry Page, Alphabet

Wise advisors

Larry Page, CEO of Alphabet (Google’s parent company), was once named by “Fortune” as “the world’s most daring CEO” in its article identifying him as “Businessperson of the Year” and #1 in Forbes’ “America’s Most Popular Chief Executives” as identified by his own employees. 

Interestingly though, he can largely credit his success—and his fortune—to his decision to surround himself with and listen to smart people around him. While exploring doctoral dissertation options, Page started thinking about graphing the structure of the world wide web to better understand the format and linkage driving it. 

His supervisor recognized the value of the idea and encouraged him to explore where this would lead. Page wisely followed that advice, enlisting the help of his friend, Sergey Brin, who agreed to sign on to the project. They then started building out the ideas and technologies for using this approach to search the web, even printing a paper on the theories and approaches behind it. What if he hadn’t listened to the advisor encouraging him to explore the project? Can you imagine a world without Google? 

There’s an arguably even greater example of Page listening to leadership mentors: in 2001, after discussing with some of the most successful CEOs, like Apple’s Steve Jobs and Intel’s Andrew Grove, he warmed to the idea (proposed by potential investors) that he step aside and bring in someone with more experience to lead the organization. This opportunity allowed him to maintain a great deal of influence in the organization while maturing in life and business. 

In the 10 years before stepping back in as CEO, Page determined that many tenets of his young, passionate leadership style were counterproductive to achieving results in an organization of Google’s current size. He also used this time for smaller “pet projects” like purchasing Android, which quickly became the world’s most popular mobile operating system. If Page had refused to take that time away from his CEO duties, who’s to say where Google would be today? We all need leadership mentors who can help us make difficult but wise decisions.

Jordan Peele, Monkeypaw Productions

Opening doors

Well-known as the second half of the comedy duo “Key & Peele,” as well as the director of the hit movie “Us” and writer and director of 2017’s widely successful, Oscar-winning movie “Get Out,” Jordan Peele is Founder and CEO of Monkeypaw Productions. 

Monkeypaw operates with purpose, and the website even spells out the company’s goals of entertaining while exploring current social issues and targeting unique perspectives and underrepresented voices. In an effort to help up-and-comers succeed in the business and tap into new lines of creativity, they even held open script submissions, a step rarely undertaken by established and successful production companies. Peele’s desire to bring diversity and variety to the film industry is just one reason he’s gained so much respect as a CEO.

Lynsi Snyder, In-N-Out

Great work atmosphere

Growing up in the family that founded In-N-Out, Lynsi Snyder has had many opportunities to see what works well and what doesn’t. But we’ve seen heirs of family businesses fail many times, so success certainly wasn’t a given for Snyder. 

She focuses heavily on the culture established in the beginning, when her grandparents set the expectation for taking care of employees and guests alike. The benefits show through when employees are surveyed, with the majority saying positive things about their treatment by the organization, which includes solid career paths, great benefits for full and part-time workers, and a starting salary far above the quick-service industry norm. 

In fact, Snyder’s employees ranked her higher than any other female CEO in the U.S. in Glassdoor’s annual survey. When interviewed by Glassdoor, she had this to say: “Whatever his or her career goals might be, my hope is that anyone who spends time as an In-N-Out Associate finds the experience valuable.”  

Jeff Weiner, LinkedIn (part of Microsoft)

Taking care of the team first

Jeff Weiner has a 97% approval rating through Glassdoor’s anonymous survey of employees, putting him near the top on their Employees’ Choice of Top CEOs for 2019. Likely playing a role in that is his desire to ensure his people are taken care of. 

In 2016, LinkedIn’s stock took a 40% plunge in share price when results fell below analyst expectations. Concerned about the impact on his team, he directed the compensation committee to reallocate his approximately $14M stock package to a pool for employees. 

Oprah Winfrey, OWN

Genuine desire to give back

Oprah Winfrey worked incredibly hard to get where she is, and she takes seriously her responsibility to give back. 

Her philanthropic efforts have even led to her receiving the Presidential Medal of Freedom in 2013, the Jean Hersholt Humanitarian Award in 2011, and the first Bob Hope Humanitarian Award in 2002. 

In addition to her well-known international work, including her Leadership Academy for Girls in South Africa and her funding for new homes in the southern US following Hurricane Katrina, Winfrey makes it a point to give back to her staff. In 2006, to celebrate 20 years on national TV, she took her entire staff and their families (1000+ people) on vacation to Hawaii to thank them for their hard work. In 2009, she also took her staff on a Mediterranean cruise. 

What About You?

These great CEOs knew that they needed wise counsel from other experienced leaders to get where they are today. 

How do you maximize your potential and push past the barriers in your way? If you need help learning how to walk away from work and take a break, change your mind, take a risk, or engage your people more completely, an executive coach can benefit anyone who is ready to grow and become a better leader. 

To learn how to be a great CEO yourself—or just a better leader—talk to one of our coaches today!