Get All Access for $5/mo

Should You Have a 'Shadow' Like Jeff Bezos Does? Letting an employee follow you around can be a great way to groom up-and-coming talent.

By Brian Patrick Eha

Opinions expressed by Entrepreneur contributors are their own.

REUTERS
Jeff Bezos

If you like the idea of someone playing Boswell to your Samuel Johnson, dogging your steps and hanging on your every word, you and Jeff Bezos have something in common.

In the late 1990s, Amazon's visionary founder and chief executive created a new position – that of his "shadow," someone who would follow him around, join his meetings, and serve as a sounding board for his at-times impractical ideas. "I was a receptacle for him for any of the 19 ongoing activities in his brain that didn't have a place in the normal organization," Stig Leschly, an early shadow, told Bloomberg Businessweek. "It was honest to God one of the most extraordinary things a young person can do."

Over time, as shadows came and went, the position became more organized. According to Businessweek, Amazon executive Andy Jassy is the man who made the position what it is today. "I asked Jeff what success would look like," he told Brad Stone, author of The Everything Store: Jeff Bezos and the Age of Amazon (Little, Brown and Co., 2013). "He said success would be if I got to know him and he got to know me and we built trust in each other." Jassy became Bezos's "quasi-chief of staff," Stone reports.

Related: Hoping to Attract More Startups, Amazon Rolls Out AWS Activate

After two years of following Bezos around, Jassy was the CEO's pick to head up Amazon Web Services, a division that Ben Schachter, an analyst with Macquarie Capital, estimates will rake in $3.8 billion in 2013. Thanks to successes like that, many of Amazon's other senior executives now reportedly have their own shadows.

And Amazon is not the only company to employ an executive shadow. In fact, Bezos got the idea from Amazon investor John Doerr, who saw how well it worked at Intel when he worked there decades ago, according to Businessweek.

Having such a close confidante holds obvious appeal for busy CEOs. So, should you let a bright comer be your shadow? The potential benefit is twofold. You will gain a valuable check on your thinking, and a high-potential employee will be groomed for leadership, both of which benefit the company as a whole.

On the other hand, you may end up training your competition, if the employee decides to seek an executive position elsewhere after shadowing you. But that is a risk with every employee, and the closeness of a shadow position presents an unmatched opportunity to inspire loyalty. Maybe the question should be "Can you risk not cultivating a potential star?"

Would you appoint someone from within your company to be your shadow? Why or why not? Sound off in the comments below.

Related: Keep Your Employees Loyal By Encouraging Them to Pursue Their Own Projects and Passions

Brian Patrick Eha is a freelance journalist and former assistant editor at Entrepreneur.com. He is writing a book about the global phenomenon of Bitcoin for Portfolio, an imprint of Penguin Random House. It will be published in 2015.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Side Hustle

At 16, She Started a Side Hustle While 'Stuck at Home.' Now It's on Track to Earn Over $3.1 Million This Year.

Evangelina Petrakis, 21, was in high school when she posted on social media for fun — then realized a business opportunity.

Health & Wellness

I'm a CEO, Founder and Father of 2 — Here Are 3 Practices That Help Me Maintain My Sanity.

This is a combination of active practices that I've put together over a decade of my intense entrepreneurial journey.

Business News

Remote Work Enthusiast Kevin O'Leary Does TV Appearance Wearing Suit Jacket, Tie and Pajama Bottoms

"Shark Tank" star Kevin O'Leary looks all business—until you see the wide view.

Business News

Are Apple Smart Glasses in the Works? Apple Is Eyeing Meta's Ran-Ban Success Story, According to a New Report.

Meta has sold more than 700,000 pairs of smart glasses, with demand even ahead of supply at one point.

Money & Finance

The 'Richest' U.S. City Probably Isn't Where You Think It Is

It's not located in New York or California.

Business News

Hybrid Workers Were Put to the Test Against Fully In-Office Employees — Here's Who Came Out On Top

Productivity barely changed whether employees were in the office or not. However, hybrid workers reported better job satisfaction than in-office workers.