4 CEOs Reveal How to Keep Getting Promoted

by | Dec 9, 2015 | Life

A pat on the back and a “great job” from your boss are nice, but a fatter paycheck and bigger office are even better. So what’s the smartest strategy for consistently getting promoted?

Instead of asking career experts for the answer, we tapped CEOs for their tried-and-true tricks. Because who better to tell you how to make it to the top than the people who are already there?

Related: Here’s How To Land Your Dream Job

1. Speak Your Mind

Tony Haile was 30 and directionless, having spent his 20s crewing sailboats across the Atlantic and participating in polar expeditions.

“I had nothing approximating a real job on my resume, so I was basically unemployed and probably unemployable by any normal company,” he says.

One day, Haile took a look at the business plan for a friend’s potential investment opportunity. Since he had nothing else to do, Haile wrote six pages of notes on “why the company’s plan sucked, and what they should do instead,” he says.

The memo made its way to a bunch of people, including execs at that company. But when they called Haile, they didn’t chew him out—they offered him a job as Chief Strategy Officer.

Two years later, the web analytics company ChartBeat named Haile CEO.

Related: “I Didn’t Speak A Single Word For 10 Days—Here’s What I Learned”

“As CEO, you constantly have a thousand broken things to deal with,” Haile says. The most valuable people are those who can take problems off the boss’s hands—like delivering an improved business proposal without even being asked.

Just make sure if you’re going to challenge the higher ups or point out a flaw in a business plan or project, you support it with facts and also bring a solution, Haile adds.

And although bigwigs ultimately rewarded Haile for his brashness, he says it’s just as important to know when to shut up.

“I owe the vast majority of what success I’ve had to being lucky enough to surround myself with people smarter than me and knowing that I should listen to them more than I talk,” says Haile.

2. Strengthen Your Weaknesses

When Perk Perkins was named CEO of Orvis in 1992, he was set up for failure.

The sporting goods company had another person in mind for the role, but he resigned before taking over. That’s when the board asked Perkins to step up from his role as president.

At that time, Orvis was floundering, and one of Perkins’ first tasks as CEO was to take the company through Chapter 11.

“The experience drained me and shook my confidence badly,” Perkins says.

Instead of trying to figure out how to turn a failing business into a success all by himself, Perkins admitted he needed more guidance. He enrolled in an intense, 3-month business course at Harvard.

He went in simply to learn the basics of running a business, but the course ultimately benefitted him in more ways than that. It gave him back his confidence and armed him with the assertiveness he needed to turn the company back around.

Related: The Best Money Advice We’ve Ever Overheard

More than two decades later, Perkins has almost quadrupled Orvis’ profits.

Hitting the books before you’re promoted can prepare you for the job you want, says Perkins. After all, the ability to learn is one of the best abilities a leader can have.

Ask your boss what kind of skills you’ll need when it comes time for a promotion, and if he can refer you to any continuing education programs. For example, Perkins says correspondence MBAs—or a degree obtained through online courses—have helped many managers succeed at Orvis.

It’ll show him or her how serious you are about your career trajectory, explains Perkins. It demonstrates that you’re not complacent—you’re always willing to stretch yourself to be better, smarter, more capable. Talk to your human resources department about tuition reimbursement packages your company might offer.

Unable to take night or online courses? Seek out self-help books that are geared toward your career field or improving your leadership or management skills. Our pick: Good to Great by Jim Collins.

3. Don’t Just Say You’re Ambitious—Show It 

When gunning for a promotion, you’re asking your boss to bet on you—so you need to convince him you’re ready for the extra responsibility.

Take Jim Weber. When he worked at the camping company Coleman in his 30s, he set his sights on running a business someday.

He knew he’d need to lead a team of people, but as vice president of corporate development, he had never managed a single employee.

So he drafted a comprehensive plan for turning around one of Coleman’s fledgling businesses.

Related: A Promotion Requires Hard Work, Dedication and a Cheesy Song. Grab a Mic

The CEO was so impressed with Weber’s initiative and investigation that he decided to put his strategy into action—and make Weber the president of the division.

Today, Weber is the CEO of Brooks Running, and seeks out curious employees to join him atop the corporate ladder.

Follow their lead: Ask your boss what his or her biggest problem is, and how you can solve it. Then put all of your energy into delivering success, says Weber.

4. If You Can’t Move Up, Move Forward

In 2002, Scott Allan was the COO of an internet payment startup in Silicon Valley. He and his team had raised $20 million in venture funding and were getting ready to launch new products when the market suddenly shifted.

Almost overnight, Allan was given 6 months to either shut down or sell the company.

“I felt like my dreams were crumbling,” says Allan. “I carried the burden of this decision and felt responsible for the company missing its window of opportunity.”

But 18 months after Allan sold the business, the company that bought it promoted Allan to vice president/general manager of business. It was technically a demotion from his previous role, but the new gig promised insight he couldn’t get as COO.

Related: 4 Ways That Exercise Improves Your Work Life

“What I learned the hard way is that sometimes you go sideways, sometimes you take a step backward, and then other times you take a big leap forward,” he says.

Career trajectory isn’t always up—it can be more of a winding path. And that’s not a bad thing: Knowing how each area of a business functions can better prepare you to run the whole show, says Allan.

In his case, Allan became intimately familiar with business development, product engineering, marketing, and operations through his linear roles. He was also able to network with execs in other divisions.

All that experience prepared Allan for his current gig: CEO for Hydro Flask, a company that produces stainless-steel water bottles.

Sometimes, Allan says, it’s better to leave a higher title and pay at a company without opportunities to learn about a new industry or move to a destination with a better future.

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