Twenty-seven years after Jeff Bezos launched what was first called Cadabra Incorporated out of his Seattle garage, his era as Amazon’s CEO comes to a close today, July 5, 2021. His successor, Andy Jassy, now has the ultimate unenviable task: Following in the footsteps of a founder-CEO who grew the company from a sapling into a publicly traded firm with an almost $2 trillion dollar market cap and unrivaled market power.

How should Jassy, who currently runs Amazon Web Services, approach the challenge? Past CEO transitions point to a few suggested moves for Amazon’s incoming chief executive: 

 

Jassy would do well to avoid becoming a founder-CEO “clone.” When Steve Jobs departed Apple, he gave this precise advice to his successor, Tim Cook. “Don’t ask what I would do,” he reportedly counseled Cook, “Do what’s right.”

Cook seems to have taken this advice to heart. He’s leaned on his engineering and MBA training and focused on the arcana of Apple’s operations. While he was criticized early on for his lack of visionary product leadership, his focus on AirPods and smart watches, as well as Apple’s subscription businesses, tied together the Apple ecosystem. 

That attention to detail extended the elegance and simplicity of Apple’s DNA into new areas, and thereby confounded critics who said that Apple in the post-Jobs era was done for. The financial results speak for themselves: Since Cook’s takeover in 2011, Apple has doubled revenues and profits as well as increased its market cap a staggering 5.5 times to ~$2 trillion. 

Jassy should draw from Cook’s experience. In running AWS, Jassy has already absorbed enough Amazon DNA to last a lifetime. Thus, his goal ought to be to make the company his own—not intuiting what his old boss might have done

 

Satya Nadella became the third CEO at Microsoft after Steve Ballmer and Bill Gates, both big-personality CEOs and tough acts to follow. On his way out, Ballmer reportedly told Nadella, “Be bold and be right. If you’re not bold, you’re not going to do much of anything. If you’re not right, you’re not going to be here.”

It was useful advice, especially because the Microsoft that Nadella took over in 2014 was not as “bold” as it had been in prior eras. Many technology observers noted that the Redmond-based giant had whiffed on nearly all the big shifts in technology—social networking, search, smartphones, and cloud computing. In each case, it lost market share and customers to the other tech giants, including Amazon, Google, and Apple.

Nadella initiated a “cultural reboot,” bringing the organization’s focus back to its heritage. He pushed a company-wide narrative about Microsoft’s origins as a platform player—the technology enabler of others’ technologies. He had to act boldly—reorganizing Microsoft, pursuing acquisitions like LinkedIn and GitHub, letting go of long-time executives, and even partnering with companies like Salesforce, with whom Microsoft had previously battled in court.

Today, Satya Nadella is regarded as the CEO who, per one headline, “brought Microsoft back from the brink of irrelevance.” Shareholders have been amply rewarded during the Nadella tenure as well, with over $1 trillion in returns and more growth forecasted on the horizon.

Nadella’s decision to reboot and push Microsoft to “be bold” is good counsel for Jassy, particularly as he follows on the heels of a CEO known for bold bets.

Donn Tatum, the first non-Disney family member to become Disney CEO, couldn’t have imagined a worse outcome than his push to move the company out of G-rated movies and into PG-rated ones. When films like Black Hole and Dragonslayer debuted in 1978 and 1981, they disappointed at the box office—and gave ammunition to critics that said that Tatum should have stuck with the family-friendly lighter fare that had made Disney into a powerhouse. At the same time, though, Disney was losing the critical teenage audience, who thought the company just made “movies for kids.”

But those cinematic stumbles, while painful, paved the way for Disney to debut films like Tron in 1982 and later blockbuster hits like The Lion King, the Pirates of the Caribbean series, and Frozen. Tatum pushed the company to take necessary risks, which paid off over the long haul.

The Lesson

The lesson: Jassy ought not to be afraid to have his own failures, particularly as he begins to make Amazon his own and pushes its boundaries beyond its current businesses. Admittedly, Jassy may not have the safety net that Bezos had with Wall Street investors. Bezos could afford failures like the Fire Phone based on his founder status and stock holdings exceeding 10 percent of total Amazon stock. 

But Jassy, who owns less than 1 percent of Amazon, shouldn’t be afraid to take big steps. In a way, he may be one of the best prepared incoming CEOs in history. The division of Amazon he runs, Amazon Web Services, after all, is about as far afield from the bookselling website launched in Seattle those three decades ago. AWS today is profitable and powerful—and became so under Jassy’s stewardship. 

Now begins the Jassy regime at Amazon, and while the new boss has been simmering in Amazon’s cultural stew for some time, he would do well to study the examples of prior CEO transitions before him. There is a great deal to learn from those who have taken the reins at comparable companies, and if Jassy is anything like the founder-CEO he is replacing—and who was famous for “going to school” on business titans before him—he will mine those hinge moments at companies for the lessons that can propel Amazon to its next thirty years of success.