Tim Cook’s impending retirement as Apple’s CEO marks the end of an era — the years  when the Apple-versus-Microsoft fight dominated the tech world.

Of course, it’s been a long time since those two companies ruled by themselves. These days, Google, Meta, OpenAI, Anthropic and Amazon are just as influential. Still, Cook’s decision to step down as Apple CEO on Sept. 1 to become chairman of Apple’s board is a good time to revisit the debate: who’s the better leader, Cook or Microsoft CEO Satya Nadella?

Both men faced the unenviable task of replacing larger-than-life company founders and visionaries. Cook took over as CEO at Apple in August 2011, two months before Steve Jobs died. Nadella ascended to the top job at Microsoft in February 2014 after Steve Ballmer stepped down. (Ballmer had replaced founder Bill Gates as CEO in 2000.)

To determine who’s been a better leader — and positioned their companies better for future success — we need to look at the challenges each faced as CEO.

Cook’s and Nadella’s biggest challenges

In the 10 years before Cook took over at Apple, the company saw an unprecedented run of innovation under Jobs, creating products that redefined technology – not only what it could do but also shaping the way people live and work.

The iPod in 2001 launched the digital music revolution. That was followed two years later by iTunes, which completed Apple’s dominance in digital music. The iPhone in 2007 single-handedly created the mobile revolution, along with the follow-on App Store in 2008. That same year, Apple launched the iPad. Then, in May 2011, Jobs unveiled iCloud.

Cook’s two greatest challenges when he took over: make as much money as possible from Jobs’ innovations and continue to create groundbreaking products.

Nadella took over at Microsoft during what has been called the company’s “lost decade.” Quite simply the company had stagnated, launching no new significant products while milking its cash cow, Windows, as much as it could.

In that decade Microsoft couldn’t even handle Windows properly. Windows Vista, launched in 2007, is generally regarded as the worst version of Windows ever. And in  2012, Microsoft released Windows 8, also considered a big miss.

It’s said that, to a man with a hammer, the entire world looks like a nail. The same could be said about Ballmer and Windows: he saw it as the solution to every tech problem that existed. (Gates, by then board chairman, agreed.)

That myopic view led to several disasters, most notably missing out on the mobile phone revolution — even though Microsoft had in 2003 launched Windows Mobile, a smartphone operating system, well before Apple.

Nadella’s greatest challenges were legion: create innovative products, pivot away from Windows, and fix a toxic company culture that had executives spending their energy on turf battles.

How Cook has fared at Apple

By any measure, Cook has been a superb technocratic leader at Apple. His big achievements were in the behind-the-scenes nuts-and-bolts of manufacturing that don’t make headlines, but that helped Apple cash in on Jobs’ many innovations and become a multi-trillion-dollar company.

Most important, he transformed Apple’s supply chain. It was a complicated mess when Cook took over as CEO. He streamlined things by reducing the number of suppliers and manufacturers Apple dealt with. He also put into effect a “just-in-time” delivery of components that the company needed, reducing costs and making the manufacturing process more efficient and more nimble in responding to a fast-changing market.

He also recognized the value of services, transforming iCloud, Apple Music, the App Store, and Apple Pay into financial juggernauts, and rolling out Apple TV+ to critical acclaim. But Cook never succeeded in developing breakthroughs like the iPhone. The Apple Watch has been a hit, but it didn’t change the tech world in the way many of Jobs’ products did. (The jury is still out on the Vision Pro.)

Cook also completely missed out on AI. Apple is so far behind in that area at the moment you can’t even count the company as an also-ran. And that might spell trouble for the future. Making money from aging technologies might not be enough for Apple to remain dominant in the coming years when AI will be king.

Nadella’s tenure at Microsoft

Everyone knew Microsoft was getting a Cook-style technocrat when Nadella became CEO. What surprised everyone — including me — was that it got one of tech’s great visionaries as well.

Nadella took over a moribund company and accomplished one of tech’s greatest turnarounds. He put an end to the company’s divisive culture, de-emphasized the over reliance on Windows, increased its cloud presence, and killed Windows Phone, which had cost the company billions and remained a drag on its success.

Eventually, he reorganized the company to make it cloud-centric rather than Windows-centric, getting rid of a number of problematic executives, including Terry Myerson, who had been executive vice president of its Windows and devices business. Microsoft became a cloud company more than an operating system company.

He also forged a better relationship with customers. Rather than try to ram Windows down their throats at every opportunity, as Gates and Ballmer did, he embraced making Microsoft technology work with competing products. For example, he allowed Linux to run  SQL Server. He also bought the developer platform GitHub, and let it remain open and independent rather than become Microsoft-focused.

Then along came AI. Nadella recognized AI was the future, and by investing in OpenAI, forging relationships with other AI companies including Anthropic, and building an internal powerhouse of AI development, Microsoft became one of the world’s foremost AI companies.

The winner

So who’s been the better CEO? 

Cook took over a company with a wealth of ground-breaking products that had created entirely new markets, and did a great job of milking them for all they were worth. He’s certainly been great at making money for Apple. But he’s leaving behind a company that despite its profitability, faces a problematic future in an AI-first world.

Nadella took over a company whose innovative days were far behind it, rebuilt it from the ground up, killed off money-losing tech like Windows Phone, de-emphasized Windows, and then organized the company around the cloud.

In the last few years, he recognized the potential of AI and has been organizing the company around that. Microsoft is better positioned for the AI future than Apple. 

For those reasons, Nadella comes out on top.