Can Tim Cook Fill Steve Jobs’ Shoes? Other Heirs to Superstar CEOs

Now that Steve Jobs has stepped down as Apple’s CEO, it’s an understatement to say that his successor, Apple COO Tim Cook, has mighty big shoes to fill. Cook–who Jobs singled out to replace himself–joins an exclusive group of newly appointed tech CEOs who faced the challenge of repeating the phenomenal success of visionary forebears.

AOL, Google, and Microsoft have all been at similar junctures with unproven leaders thrust into the spotlight with big expectations. Can Cook replace Jobs at Apple? Here is a look back at some others who tried to walk in the paths of their predecessors.

Transition at Microsoft

Ray Ozzie had an impressive tech resume as the creator of Lotus Notes when he took over for Bill Gates as Microsoft’s chief software architect in 2005. But he had trouble developing the sort of following within the company that Gates enjoyed. And when Ozzie announced his retirement last year, Microsoft employees told the Wall Street Journal that he had failed to live up to Gates’ reputation as a strong public ambassador.

Ozzie started his new job at Microsoft as a chief technical officer after Microsoft purchased the company he owned, Groove Networks. Just before taking over, he issued a now-notorious memo on the need to move more toward cloud-based services. In the years that followed, that vision appeared to clash with those of Microsoft executives. Ozzie led a push to move Microsoft further into the cloud and contributed to Windows Live Mesh and Windows Azure, only to see those efforts moved to different divisions of the company.

While Windows Live has survived, Microsoft still hasn’t fully embraced Ozzie’s vision. It’s believed that a re-focusing on Windows and Office products championed by CEO Steve Ballmer may have nudged Ozzie out of the chief architect’s chair in 2010 to focus on entertainment projects within the company. Perhaps back-to-back visionaries was more than Redmond could handle.

Takeaway for Cook

The good news for Cook is that he’s unlikely to face the same problems Ozzie did. During his tenure, both analysts and sources inside Redmond noted that Ozzie lacked the evangelical chops that Gates had, a quality key to influencing employees within Microsoft’s highly competitive culture. Cook, while not quite the pitch man that Jobs has been, knows his company from top to bottom and is well-respected inside and outside of Cupertino. Promoting from within the ranks is clearly a smart move for Apple’s fraternal corporate culture. Maybe it would have been smart at Microsoft, too.

Dawn of a New Day at AOL

By the time AOL’s visionary founder Steve Case stepped away from the AOL Time Warner chairmanship in 2003, the 2000 merger of old and new media giants was already becoming one of the most spectacular failures in corporate history. His move represented just how much the massive new company’s AOL/Internet division had faltered since the merger and dot-com bust. AOL Time Warner reported nearly a hundred billion dollars in losses for 2002.

CEO Dick Parsons was already in charge of day-to-day operations when Case announced he wouldn’t seek another term as AOL president. Parsons had consolidated his control after years as president of pre-merger Time Warner. His background was neither in technology nor media, however, but as an attorney and power broker with close ties to the Rockefeller family.

Ultimately, Parsons would spend a few years trying to turn things around and preparing AOL for a planned transition to becoming primarily a content company, as its dominance as an ISP faded. Case left the Time Warner board in 2005, and Parsons followed him out in 2007. In 2009 Parsons became chairman of Citigroup. AOL continues to struggle to remake itself, even after Time Warner finally spun it off in 2010.

Takeaway for Cook

Apple’s Cook finds himself in a much stronger position than anyone involved with Time Warner over the last decade. Case was already no longer widely admired as a tech titan when he gave up his chairmanship. Parsons, as CEO, was clearly in a similar position of power and responsibility within his company as Cook has been as Jobs’ right-hand man for over a decade. But Apple and Time Warner could scarcely be in more different positions at the time that their respective industry legends stepped down. In other words, don’t expect to see Cook taking his leave from California to head for the banking industry anytime soon.

Musical Chairs at Google

First, Larry Page and Sergey Brin, then Eric Schmidt, and now Larry Page. Eric Schmidt’s years of experience at Sun, Novell and Xerox PARC provided a young and goofy startup with the adult supervision it needed to continue reimagining the online world that its engineer founders started just a few years earlier.

From 2001 to this year, Schmidt took Google from 200 employees to more than 20,000. But Brin and Page remained at Schmidt’s side. As Google grew, Schmidt’s role seemed to focus more and more on external matters, such as serving as company ambassador in Washington, D.C. or at a festival in Aspen.

It was announced in January that Page would take over as CEO and Schmidt would shift to company chairman to focus more on external relationships. Schmidt noted that managing the company had become “more complicated.” In other words, the Google machine had been fully assembled and well maintained by a master builder, and now the engineers wanted to take it out for a spin.

While Brin and Page may have had the original vision for Google, Schmidt helped broaden their view and encouraged remarkable growth. The Schmidt decade saw Google corner the online advertising market while launching successful efforts like Gmail, and using deep pockets to acquire big names like YouTube. Page was studying and making decisions at Schmidt’s side, but Schmidt’s decades of experience in technology and business, as well as charisma, helped realize so much potential.

Schmidt says Page is ready to proceed without his mentorship. Since taking over in April, Page’s Google certainly hasn’t been afraid to be bold, as seen with the launch of Google+ and the purchase of Motorola Mobility.

Takeaway for Cook

Like Page, Cook also spent years at the side of a business-minded tech visionary, and transitions are happening in the same year at both companies. The great success of both Google and Apple in the last decade have been its remarkable abilities to scale. At Google, Schmidt took a tiny startup to a dominant global force recreating the technology sector in its own image. At Apple, Cook helped lead efforts that made it possible for Apple to ship over 100 million iPhones, such as outsourcing manufacturing to China without sacrificing product quality.

It was thought that Page might want to take Google back to its startup roots, and maybe he can influence Google’s internal culture in such a way, but the $12 billion Motorola purchase could only come from a company with growth in mind. As for Apple, Cook has certainly shown that he, too, can do growth.

Jobs’ First Exit

It’s worth remembering that when Apple pushed out Steve Jobs in1985, the company prospered for some time without him. Some of the Macintosh’s best years came while Jobs wasn’t in the building. There was the successful introduction of a number of home PCs following the landmark “1984” campaign, as well as the 1991 debut of portable PowerBooks.

Things got rough around the time Windows 95, was rising to prominence. Apple struggled under the leadership of CEO Gil Amelio, who came in in 1996 as Microsoft was rapidly gaining market share, and announced huge layoffs and changes to Apple. He cancelled the “Copland project” to create a next-generation OS. After a failed attempt to purchase BeOS, he turned to Jobs’ NeXT, buying the company and bringing Jobs back as an advisor. As Jobs returned, the company’s stock price was at a 12-year low following billion dollar losses under Amelio, who was soon ousted and replaced by Jobs in 1997.

Over the next 14 years, as we know, Jobs went on to re-build and re-shape Apple–taking it in completely new directions with the iMac, iPod, iPhone, and iPad. The company and Jobs’ focus on quality and user experience–along with marketing pizzazz–helped make each product a success.

Takeaway for Cook

This time around, Jobs is stepping down but not away. With the visionary still serving as Chairman of the Board, radical shifts in Apple’s business are unlikely. So long as Cook can keep a steady hand on the wheel, he’s likely to do just fine. He’ll be surrounded by the same team that helped build the kingdom–design master Jonathan Ive and marketing master Phil Schiller, among others.

The only question that remains is who will have the vision to push Apple even further. Cook has shown he knows how to navigate the route, but can he draw the next map without Jobs?