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Sheryl Sandberg’s Long (Overdue) Goodbye

When exactly is the right time to exit the limelight?

There are very few in tech who’ve gotten this right, but perhaps chief among those with bad timing is Sheryl Sandberg, Meta’s chief operating officer. She announced, far too late, in a long Facebook post this week and a series of repetitive press interviews, that she would be stepping down from her No. 2 role at the social media behemoth after 14 years. (She’ll remain on its board, for now at least.)

“I am not entirely sure what the future will bring,” Sandberg wrote. “I have learned no one ever is.”

Indeed not. Many are pondering the “Why now?” aspect of it — which I will get to in a minute — but as a longtime observer of one of Silicon Valley’s most powerful players and most definitely its most powerful woman, I have a more pertinent question: What took so long?

Her accomplishment of creating a truly massive, moneymaking machine out of the chaos she took on when she left Google for Facebook in 2008 is nothing short of spectacular. She has been lauded for Facebook’s tremendous success and private wealth creation and also her focus on women in the workplace in her landmark 2013 “Lean In” book, which made her a major corporate star, the likes of which tech had not seen ever and has not since.

But it adds up to one of the more unfortunate career trajectories I can think of, given that Sandberg is walking away from her tenure with a reputational hit, one that few male executives on her level have received. Many will continue to blame Sandberg for Facebook’s toxic, attention-driven business model.

The first seven years of her tenure, as Platformer’s Casey Newton noted this week, may have been pretty impressive. “For half a decade, fast-growing start-ups would talk openly about ‘finding a Sheryl’ to help them grow and mature. Sandberg was the blueprint,” he wrote.

Operative word: “was.”

Why she stayed and stayed, despite numerous mic drop moments when she could have left to grab even greater glory elsewhere was a question I began to lob at Sandberg via texts and calls, starting in 2016 after I began writing about reports on some of the seriously problematic impacts of the service.

Most urgent among them was from Maria Ressa, an investigative journalist running the Rappler news site in the Philippines. She tried to alert Facebook that year to some alarming information, including harassment and threats on the site targeting people, especially women like her, who had been critical of the extrajudicial war on drugs by the country’s brutal newly elected president, Rodrigo Duterte. Getting nowhere, she called me and others. Ressa, who won the Nobel Peace Prize last year, said in a 2018 interview with me that what was happening there was a “cautionary tale for the United States.”

Ressa was right, even if Facebook turned a blind eye to it. Soon there were also reports of Russian operations on the social network trying to influence the 2016 presidential election. Mark Zuckerberg, the C.E.O., acknowledged to Congress in 2018 that the company realized in 2016 that those operations were underway, contradicting Facebook’s earlier statements. Recall that right after the election, he scoffed that “the idea that fake news on Facebook, of which it’s a very small amount of the content, influenced the election in any way, I think, is a pretty crazy idea.”

We know how well that statement aged. As the company kept backing away from it — while trying to assess what really happened — it fell to Sandberg to try to smooth out the ripples Zuckerberg made, given that she is as sleek as he is awkward and as diplomatic as he is, well, awkward.

As the extent of the problem came into greater focus, I called Sandberg to tell her that the impact of the company’s disinformation problems was going to engulf it and turn out very badly for it.

“We are handling it,” she assured me in her patented soothing voice of reason, after I pressed her about the importance of directly dealing with the consequences of Facebook’s inventions more responsibly. I clearly sounded a little intense, because she tried to calm me down in the “we’ve got this” tone that had taken her so far in her stellar business career. But I instead grew more worried, including in my first column for The Times, nearly four years ago, in which I laid it out in pretty stark terms:

To her credit, Sandberg remained unfailingly cordial to me after that, a contrast to how most men in tech act when criticized. In the face of mounting scrutiny of Facebook — concerning data abuse, its cozying up to President Donald Trump, how Instagram negatively affects teen girls and the mounds of disinformation on the service, covering everything from vaccines to elections — Sandberg morphed into the company’s chief defender, often of the indefensible.

That included an extraordinary attempt to deflect blame from Facebook for its role in the Jan. 6 attack on the Capitol. “These events were largely organized on platforms that don’t have our abilities to stop hate, don’t have our standards and don’t have our transparency,” Sandberg said in an interview a week later, even as researchers were turning up evidence it was a key platform for organization and communication for the rioters.

And in that moment, Sandberg lost what remaining credibility she had in Washington, though she had once operated the levers of power there effortlessly. No longer, as she tethered her once pristine reputation to Zuckerberg, taking many more slings and arrows than he.

As much responsibility as Sandberg had as a top executive at the company, Zuckerberg has always been in the driver’s seat at Meta, where he is the controlling shareholder. “No matter his responsibility, he is unkillable, unfireable and untouchable, and no amount of leaning in by Ms. Sandberg or any other woman in tech is going to change that,” I noted in a 2018 column.

Thus, she, not Zuckerberg, needs to go, as Meta now leans into his bet-the-farm effort to dominate the next era via the so-called metaverse. Talented techie though he may be, I am dubious that Zuckerberg can do what needs to be done to make his virtual world a success without another Sandberg type at his side, even while throwing gobs of money at it.

Sources close to Sandberg said she considered departing many times over the years but was always waiting for the right time — perhaps a moment of victory or at least respite — that never came at the always-under-siege company.

Sandberg’s responsibility for what’s happened at Facebook — from the fortunes made to the social dangers — will be the fodder for innumerable business-school case studies. In the meantime, there’s the recent stock decline, mounting pressure from regulators and, most of all, a company that for years has needed a radical change to face an uncertain future.

So that “Why now?” question pretty much answers itself: It’s time.

4 Questions

James Kirchick is a longtime reporter and foreign correspondent whose latest book is “Secret City: The Hidden History of Gay Washington.” I’ve edited his answers.

We’re at a peculiar time in Washington, when gay people have never been freer to be who they are and yet retrograde forces are mounting across the country. How do you assess this moment in the sprawling history of secret lives you recount?

The story of gay progress in America is one of action and reaction. World War II was a national coming-out experience for gay people, many of whom had never met another gay person before. It was followed by a nationwide sex panic and the Lavender Scare, the purge of gay government workers beginning in 1950. The 1969 Stonewall uprising and subsequent era of gay liberation were followed by Anita Bryant’s Save Our Children campaign to repeal anti-discrimination ordinances protecting gay people. After “Ellen,” we saw an attempt to enshrine anti-gay discrimination in the Constitution. Now, at a time of unprecedented gay visibility and societal acceptance, there is this talk of “groomers” preying on children. In the moment, it’s easy to feel besieged, but surveying the broad sweep of history, you realize that it’s part of a recurring pattern and that the trend line is ultimately positive.

When I was younger and thinking of a career in either the military or intelligence, the ability for out people like me to work there was limited, because of purported national security concerns. How has that environment changed?

The ban on gay people receiving security clearances, imposed via executive order by Dwight Eisenhower in 1953 on the supposed grounds that they were inherently susceptible to blackmail, was repealed by Bill Clinton in 1995. Since then, gay people have served openly across the national security state. Donald Trump, believe it or not, appointed the first openly gay person to head the intelligence community. Enhanced powers of surveillance have not made being gay any more of a liability.

The New York Times review of your book reads, “The very skills gay people had to develop to survive — studiousness, compartmentalization, discretion, itinerancy — made them uniquely skilled, Kirchick points out, to sensitive tasks like espionage or high-level advising.” That seems like an old trope that is no longer true, but does it persist, to the detriment of those who continue to be closeted?

Washington power politics can create perverse incentives for those who want to play its game, and for a long time, it was one for which closeted gay people, and closeted gay men in particular, were well suited. You see this especially in my chapters on the Reagan era, where I profile a series of high-powered, conservative, closeted gay men such as public relations guru Bob Gray, activist Terry Dolan, contra fund-raiser Spitz Channell and lobbyist Craig Spence. None of them emerged from that period unscathed. Two of them died of the disease the Reagan administration they supported was doing little to fight, and another was convicted of conspiring to defraud the government. As the reign of the closet recedes from American life, so has a certain archetype of gay courtiers to political power. That’s something for which we should be grateful.

The most famous example of a gay person in tech whose career was ruined just for being gay was Alan Turing, World War II’s famed code breaker. In your book, whose tragedy of dashed promise struck you most?

I found the story of Bob Waldron particularly tragic. Waldron worked as a close aide to Lyndon Johnson, first while Johnson was Senate majority leader, then vice president and, for a few short weeks after the Kennedy assassination, while Johnson was commander in chief. A government background check located a man who told investigators that Waldron had tried to sleep with him. Johnson fired Waldron instantly. One of the most arresting passages in my book is the letter I discovered in Waldron’s F.B.I. file, addressed to the man who outed him, in which Waldron wrote that, upon being named as a homosexual, “I will be marked by our society — which does not permit a return.” That was the fate awaiting gay people whose secret was exposed in Cold War Washington: permanent banishment.

In which I agree with Musk …

Elon Musk’s recent performative nonsense on Twitter around culture wars is “like if Ben Shapiro had a passing interest in satellites,” the New York Times columnist Kevin Roose aptly put it on “Sway” this week, but I found myself agreeing with the voluble Tesla chief exec’s take on his employees’ return to office.

Musk said in a memo that because he thinks great products cannot be made without in-person interaction, its executives should spend a minimum of 40 hours per week in the office. Or they can quit.

“This is less than we ask of factory workers,” Musk wrote, although he did say he would personally review and approve any exceptions. (Think talented and prickly software engineers.) On Twitter, when pressed to address those “who think coming into work is an antiquated concept,” he wrote, “They should pretend to work somewhere else.”

OK, that made me laugh. As different companies make different rules, it will be up to employees to decide what they prefer — but the Great Reassessment around the new workplace is far from over.


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