The metamorphosis of Silicon Valley CEOs.
When Joe Barton, a Republican congressman from Texas, greeted Jack Dorsey at a congressional hearing last week, he sounded flummoxed.
“I don’t know what a Twitter CEO should look like,” Barton said. “But you don’t look like what a CEO of Twitter should look like.”
The congressman had a point. Dorsey — who sported a nose ring, a popped-collar shirt and a craggy Moses beard — looked more like a hipster version of a Civil War officer than a tech icon. Yet more striking than his look was his manner before skeptical lawmakers.
Faced with tough questions, Dorsey did not mount an aggressive defense of his company and his technology, as an earlier generation of tech leader might have. Instead, he demurred, conceded mistakes and generally engaged in a nuanced and seemingly heartfelt colloquy on the difficulties of managing tech in a complex world. Even in response to Barton’s comment about his look, Dorsey was solicitous. “My mom agrees with you,” he said.
Dorsey’s testimony prompted questions about what we expect from tech leaders today — and how thoroughly what we expect has been upturned in the last few years. Since the 1980s, a common leadership archetype has loomed over the tech business: Steve Jobs and Bill Gates. Sometimes unconsciously and often deliberately, a generation of tech leaders attempted to ape the Apple and Microsoft founders’ charisma, their quirks, their style and above all their irrepressible, hard-charging confidence, to say nothing of arrogance.
Dorsey — who like the late Jobs returned to a company he co-founded in order to save it — has long drawn comparisons to Jobs. Yet the congressional testimony marked a surprising rhetorical shift. Instead of the blackturtlenecked Jobs, Dorsey sounded more like Tim Cook, the understated operations manager who replaced him
That is, Dorsey sounded less like a quotable visionary who can see beyond the horizon and more like what he actually is and ought to be — a thoughtful, accessible, transparent and, despite the beard and nose ring, kind of boring manager of a serious company whose decisions have world-changing consequences.
When it comes to tech CEOs, boring is the new black. Under the glare of global scrutiny, the daring, win-at-all-costs ethos that defined so much of the tech industry in the last couple of decades has been undergoing a thorough metamorphosis.
Mark Zuckerberg, the Facebook chief who was once the poster boy of breaking things and moving fast, is now sitting with magazine writers for lengthy, nuanced disquisitions on his failings. Last year, Uber replaced its controversy-magnet founder, Travis Kalanick, with Dara Khosrowshahi, whom almost nobody outside the tech industry had heard of before — a fact that the company regarded as an asset, not a liability.
Google once played up the nerdy antics of its founders, but now the company’s leaders are almost unidentifiable ciphers. Larry Page, who runs Alphabet, Google’s parent company, has become a recluse, and even Sundar Pichai, Google’s achingly pleasant chief, declined to appear at last week’s hearings.
Jeff Bezos, Amazon’s chief and the world’s wealthiest man, has been experimenting with a more daring fashion sense, but his leadership style has always been marked by patience and deliberate expansion — just the sort of boring, operator’s sensibility now in vogue.
Oh, and I almost forgot about Satya Nadella, Microsoft’s CEO. In my defense, everyone forgets about Nadella.
It’s no mystery why tech leaders are turning inward. “Tech is now such a huge and dominant industry,” said Joshua Reeves, the proudly boring founder and chief executive of Gusto, a startup that makes human resources software. “The fly-by-the-seat-ofyour-pants mindset is just not viable when you have a trilliondollar market capitalization or if you have more influence than many governments around the world.”
Reeves pointed out that it’s not just the big companies whose chief executives are going beige. Some of the most successful startups — from Lyft to Airbnb to Stripe to Slack to Pinterest — are run by understated un-visionaries, people who aim for functional competence over hypey salesmanship. (What hasn’t changed is gender; boring or no, just about everyone who runs a tech company is still a man.)
The tech press has also gotten tougher. Once, novelty alone would merit coverage, but in the social media age, even the tiniest misstep can be ruinous. It has become crucial to get a leader who doesn’t speak out of turn.
There is one obvious exception to my boring-is-in thesis: Elon Musk, the chief executive of Tesla and SpaceX, whose string of unconsidered tweets, taunts and other recent scandals have been anything but eye-glazing.
Musk’s odd behavior underlines the tensions at play as understated style takes over tech. There is a reason that a big, Jobsian personality was once so prized. Tech companies are leaps of faith. In their early days they exist on the knife edge of oblivion, and it is often only through a founder’s force of personality that investors, employees and the media take any notice. The most beloved founders possess an uncanny genius for selling the world on ideas that look useless, pointless or impossible before we all realize we can never live without them.
For all his flaws, Musk has long possessed such a genius. All the way back in 2006, he posted a “master plan” for Tesla that reads like a Wile E. Coyote caper: “1) Build sports car. 2) Use that money to build an affordable car. 3) Use that money to build an even more affordable car. While doing above, also provide zero-emission electric power generation options. Don’t tell anyone.”
Every few months, he makes new promises about this or that amazing thing coming soon. Each time, he reaps more attention and financing and, eventually, builds real cars that are sold to real people. In this way, Musk’s personality became a key element of not just his companies’ brands, but their business models.
But it’s a tricky, high-stakes gamble. For one thing, Musk has to deliver on his promises. More recently, another problem has eaten at this strategy: The future has been getting less obviously wonderful, so it’s hard to take any tech chief ’s assurances that their new thing will indeed be as great for the world as they say.
Back in Jobs’ day, tech was relatively uncomplicated; when the great man came bearing a new music player, you didn’t have to wonder whether it might help a foreign government steal an election. Now, after everything we have seen recently, you do have to worry about what the future may hold.