How People Describe Working for the Most Powerful Leaders on Earth

Tales from some of the best and worst leaders.


November 27, 2015

People tend to idealize top leaders. They’re savvy, brilliant, ruthless and unrelenting. Four percent of them are also psychopaths, as you might have read in my recent story on CEO Psychopaths. That’s the most psychopaths in any profession.

However, there’s the public persona – the stories you see glamorized in magazines, and there’s the reality – the stories straight from the mouth’s of those who worked with that person.

We wondered what it was really like to work for the most powerful people on earth.

Barack Obama

President Obama with his assistant, Reggie Love.
President Obama with his assistant, Reggie Love.

President Barack Obama is known for his charisma and the ability to relate to people. He’s arguably one of the coolest presidents, between his hilarious speech at the annual White House Correspondents Dinner and videos that show him killing it on the basketball court.

But nobody’s perfect. And in his tell-all book, Power Forward: My Presidential Education, Obama’s former personal assistant, Reggie Love, revealed that Obama can be kind of a asshole sometimes.

Love said that when things went wrong on the campaign trail, Obama would often give him the silent treatment. And that could be nerve wracking for Love, who was responsible for lugging all of Obama’s luggage from place to place, ordering him food, buying him clothes, babysitting his kids, apologizing when he couldn’t make it to a scheduled event, and fielding whatever else came up.

Once, Love got frustrated and told Obama that if he hadn’t stayed so long at an event, they would have been able to keep their promise and get to another. Here’s what he said happened after he blamed him for the scheduling snafu.

The air went still. It was like that eerie calm before a tornado swoops in and levels your entire house. Nobody said anything,” he wrote.

Sometimes, Love said, Obama could be surly and demanding.

There were days when he specifically wanted X (to eat),” Love wrote.

And Lord help me if he’d made his mind up about what he wanted and I delivered the wrong thing. Or if it came with mayo. Or was undercooked. Or soggy. If there was one thing you didn’t want to watch, it was the time-pressed candidate scraping a gooey, loathed condiment off the only food he was going to eat for the next seven hours.

Steve Jobs

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Former Apple CEO Steve Jobs is an inspiration to many and the de-facto patron saint of iPhones. He was an incredibly smart, driven and creative leader in his own right. Volumes have been spilled about his personality and the work he did. But I get the feeling that people sometimes forget about his personal flaws.

A friend of mine used to work for Apple. I remember her telling me that one day she was walking past a meeting and heard a man screaming at the top of his lungs. She couldn’t believe anyone would yell that way in the office and peered in quickly to see who it was. Sure enough, Jobs, then CEO, was the culprit.

And that’s only one story. When Stanford professor Robert Sutton was researching his book, The No Asshole Rule: Building a Civilized Workplace and Surviving One That Isn’t, he interviewed a number of Silicon Valley leaders who sincerely believed that leaders need to be mean and ruthless to build an amazing company — just like Jobs was, the Atlantic reported.

Even people who worked with Jobs told me that they’d seen him make people cry many times, but that 80 percent of the time he was right, ” Sutton said. “It is troubling that there’s this notion in our culture that if you’re a winner, it’s okay to be an asshole.”

Former Apple employee Brett Bilbrey wrote on Quora that the first time he met jobs was when he was preparing to give a presentation. He was new. Jobs spotted him, walked up and asked, “’Are you smart? Do you know what you’re talking about? Are you going to waste my time?’” When he didn’t respond right away, he said Jobs promptly moved on as if nothing had happened and said, “’Good, let’s get started.’”

In the biography on Jobs by Walter Isaacson, Isaacson interviewed Jonathan Ive, Apple’s Chief Design Officer. According to the book, Ive knew the darker side of Job’s personality, too.

Ives recounted the story of a business trip the two had taken to London. He had to choose a hotel, so he picked a peaceful, 5-star boutique hotel that he thought Jobs would like a lot. But 5 minutes after they checked in, he got a call from Jobs.

I hate my room. It’s a piece of shit, let’s go,’” Ive recounted of Jobs. Then, he said, Jobs went down to the lobby and told the shocked how terrible he thought the hotel was.

“’(Jobs) was a very, very sensitive guy,’” Ives said in the biography. “’That’s one of the things that makes his antisocial behavior, his rudeness, so unconscionable. I can understand why people who are thick-skinned and unfeeling can be rude, but not sensitive people… The normal rules of social engagement, he feels, don’t apply to him…’”

Elon Musk

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Elon Musk, founder of Tesla Motors and SpaceX, is another visionary I wondered about.
I know people who work at Tesla, and I can tell you they work hard. The company seems to function like a massive startup. But I’ve heard that Musk is an inspiring person to work for. Maybe that’s why it works.

“He always had a way of taking a complicated problem and making it very simple,” former employee Carden Bagwell wrote online. “He wasn’t ever rude or unprofessional, but he was never afraid to interrupt or challenge an assertion.”

Back in 2002 Musk founded SpaceX, which designs, manufactures, and launches rockets and spacecraft.

Dolly Singh worked as the Head of Talent Acquisition at SpaceX and said that Musk’s leadership was extremely inspiring.

She wrote about the launch of one of the company’s Falcon 1 a spacecraft in Aug. 2008. Musk had reportedly put $100 million of his own money and previously said that the company had about three tries to successfully launch a rocket into space. Unfortunately, after a great start on its third try, the rocket malfunctioned.

“The mood in the building hung thick with despair. You have to keep in mind that by this point SpaceX was 6 years old, and many people have been working 70-80+ hours a week, swimming against extremely powerful currents, like difficult barriers in technology, institution, politics, and finance —by sheer force of their blood and sweat … They had all given so much, were mentally and physically exhausted … (the) night would forever impact the future of the company, it had the potential to send the company into a downward spiral, from which we may not have ever recovered.” Singh wrote.

But she said, Musk was able to turn the difficult moment into a chance to bring people together when they might have been driven apart.

“(He) listed the half dozen or so countries who had failed to even successfully execute a first stage flight and get to outer space, a feat we had accomplished successfully that day … (He said) that we needed to pick ourselves up and dust ourselves off, because we have a lot of work to do. ‘For my part, I will never give up — and I mean never,’ and that if we stuck with him, we will win.’”

“I think most of us would have followed him into the gates of hell carrying suntan oil after that. It was the most impressive display of leadership that I have ever witnessed,” she wrote.

Sir Richard Branson

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I actually met Richard Branson one time. I saw him drinking coffee in front of a Peet’s coffee in what looked like an informal business meeting and went up to introduce myself. The people he was meeting with gave me the stink eye. But he smiled, shook my hand and even let me take a photo with him. I was impressed by how approachable he was, and how nice.

While researching Branson I was struck by his affection for achieving the impossible.

“There’s nothing more likely to get him interested in doing something than to be told it couldn’t be done,” former employee Alex Dormandy told Business Insider. Dormandy was hired by Virgin Group when he was 24. By 28, he was overseeing all of the company’s new business. By 29, he had a seat on the board.

“If you were to meet with someone who said, ‘Oh, that can’t be done,’ you’d probably say, ‘Okay, I won’t do it then,’” Dormandy said. “Richard would say that you wouldn’t succeed in business then … (He’d say), ‘If I can find a way of doing that, then we’ll make lots of money.’”

Branson used the same philosophy for deadlines, Dormandy said. He would aim to complete a project that would take 20 weeks in 12. Even if they missed the deadline, the goal would keep everyone focused, he said.

Dormandy also said that Branson had a firm belief in trusting his employees.

“I don’t think there was a single decision I made that Richard ever second-guessed me on,” he told Business Insider. He added that new hires were given small projects at first, but if they kept succeeding, got increasing levels of autonomy.

“It seems almost totally unrealistic,” Dormandy said. “(B)ut you want their trust, and they do trust you.”

Mark Zuckerberg

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Zuckerberg has one of the highest approval ratings (97%) on GlassDoor.com.

“It’s hard to imagine a CEO being easier to work with,” Facebook Engineering Manager Tom Whitnah wrote on Quora. “He listens really intently and incisively, maintains an impressive amount of context for every project…” he said, adding that Zuck treats people the same, whether they’re directors or interns.

“He generally has a clear vision for what he wants for the product,” he wrote.

But of course, no one is perfect.

“Every so often, he pulls the figurative, ‘Because I’m CEO, Bitch,’ card,” Whitnah added.

Former Facebook employee Yishan Wong had a different perspective on Zuck, who he called, “demanding and monomaniacal.”

“This is not to say that he’s mean – he’s a perfectly nice guy on a personal level. It’s just that professionally, he is focused on getting it done, and has a limited tolerance for emotional fragility in the people he needs to help him execute on that mission,” he wrote.

“My theory is that the level of personal demandingness needed to drive a global enterprise … can be too much for some people,” he said. “… (H)e is not there to ‘develop’ you – that’s your own job.

“He does have a touch of the Asperger’s. In my experience this is primarily manifested in that he does not provide much active feedback or confirmation that he is listening to you.”

Jeff Bezos

Amazon Readies Kindle Fire Update to Keep Up With Apple, Google

What about Amazon Founder Jeff Bezos?

Amazon has become notorious for a company culture that ruthlessly pursues efficiency — often at the expense of employees, according to a scathing expose the New York Times published in August.

The article said that Amazon (under Bezos), “rejects many of the popular management bromides that other corporations at least pay lip service to and has instead designed what many workers call an intricate machine propelling them to achieve Mr. Bezos’ ever-expanding ambitions.”

“I can tell you that he doesn’t dick around or beat around the bush,” former employee Willie Morris wrote on Quora. “He’s fairly direct with his opinions and expects people to make intelligent, well-thought out decisions and be able to provide answers for why something was done.”

Over and over again though, Amazon employees seem to say that Bezos is likeable because he knows how to crack a joke and put everyone at ease.

Marven Krug, another former employee, said Bezos was crazy-smart, but prone to getting “hangry” in pre-lunch meetings.

“Jeff was almost always the smartest guy in the room on virtually any subject. He deeply understood every single aspect of his business. Second, he did not suffer fools gladly. He valued his time highly (rightly so!) and had no patience for errors,” he said.

“(But) Jeff gets cranky when hungry. Postprandial meetings with him were always more successful than ones in which you were keeping him from his lunch.”

They’re all just people

With all the buzz, films, books and billions, it can be weird to think of these leaders as the regular people they really are. These tycoons have clearly risen to the top for a reason. But I was pleasantly surprised to find that most of them had been kind to the people below them.

As author J.K. Rowling wrote, “If you want to know what a man’s like, take a good look at how he treats his inferiors, not his equals.”

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