Satya Nadella reinvented Microsoft once. Can he do it in the AI era?

On a sunny day in Seattle in late September, about 50 executives representing large Microsoft customers had a rare opportunity. They could ask anything of CEO Satya Nadella.

One attendee wanted to know what Microsoft could do to help companies adapt to the artificial intelligence age. Nadella responded by emphasizing the importance of “diffusion inside the enterprise,” meaning AI tools need to be widely deployed.

“Like all things, change is always bottom up, top down, and middle up,” said Nadella, sporting a tight black crewneck and dark gray slacks, as he strode across the stage at the downtown Paccar Pavilion.

For the 59-year-old Nadella, who’s spent over half his life at Microsoft, the gathering landed at a pivotal moment, as the software giant tries to magnify its role in the AI boom. Of late, Nadella has been inserting himself more into the AI discourse, posting on X last month about the need for “deliberate pacing” in model development, and days later addressing safety fears at the All-In Summit in Los Angeles.

Despite its almost $4 trillion market cap, Microsoft has yet to break out as an AI leader. Nvidia dominates in AI chips, Anthropic and OpenAI boast the foremost models, Meta just released the first mass-market personal agent, and Google’s Gemini-powered services are popular with businesses and consumers.

Microsoft was aggressively early to AI through an investment in OpenAI, but that alliance has frayed. While the software giant has a big business in renting out chips for AI developers through its Azure cloud, its Copilot technology isn’t pervasive in the workplace, and its proprietary AI models remain niche.

The company is hosting a Windows and Surface event in San Francisco on Wednesday, describing it in an invitation as “a conversation on how local AI will shape the next chapter of the PC.”

Wall Street is lukewarm on the story. Even factoring in a sharp third-quarter rally, the stock is trailing its megacap peers and the broader Nasdaq this year, up just 7% as of Friday’s close. Microsoft hasn’t beaten the S&P 500 in a calendar year since 2023.

Tiffany Wade, co-portfolio manager at Microsoft shareholder Columbia Threadneedle, said there are a lot of unknowns about Copilot, which is the centerpiece of Nadella’s AI strategy.

“I think there needs to be a little bit more maturity of the product before we figure out actually what the best solution or what pricing is,” Wade said in an interview.

For longtime Microsoft investors, Nadella has a solid track record when it comes to navigating industry shifts. He was named CEO in 2014, succeeding Steve Ballmer, who had presided over a roughly 33% drop in the stock price during his 14-year tenure, as Microsoft slipped into the beleaguered category of legacy software.

Nadella…