As Facebook’s influence spread and Wynn-Williams’ role became more significant, she spent more time with Mark Zuckerberg, and writes that their office relationship could be quite awkward. At one point, Zuckerberg told her he had no interest in meeting the prime minister of New Zealand, not realizing the prime minister was standing with them. The social interactions weren’t always much better. During a tour of Asia, she writes, Zuckerberg suggested playing the strategy board game Settlers of Catan — and while everyone got into the nerdy spirit of it, Wynn-Williams began to suspect that her colleagues deliberately never went after their boss. “You’re letting him win,” she told them, but they denied it, while Zuckerberg, she writes, seemed totally oblivious. Years later, she again played board games with Zuckerberg on his private jet, and didn’t hold back, beating him twice in a row. Both times, she says, he accused her of cheating. “You had multiple ways to win,” she informed him the second time, laying out the better moves he could have made toward the end of the round. The dispute turned into a discussion of how Zuckerberg, in Wynn-Williams’ eyes, had mismanaged Facebook. “You’re so used to being the winner who takes all,” she told him.

Wynn-Williams was often shocked by the incurious nature of others at Facebook, she writes, especially what she saw as their seeming indifference to basic laws and norms abroad. After Joel Kaplan, a former White House chief of staff under George W. Bush, became her boss on the policy team, he moved aggressively to turn profits through political and electoral advertising in other countries — while, she claims, still having to be informed where certain Latin American nations were and that Taiwan is an island. Soon, Facebook was facing regulatory problems in other countries because of its election advertising. Apparently undeterred, Kaplan told Wynn-Williams that Facebook should establish political action committees around the world, she claims, only to learn from her that this is illegal. “Nobody wants foreigners bankrolling their elections,” she explained. In his surprise, she writes, he changed tack, saying, “We need to get moving on channeling money to our key allies offshore, you know, our most influential politicians in other countries.” Wynn-Williams said that this would be viewed as bribery and corruption, except perhaps by dictators, who would gladly take the money. “For a minute I worry that he’s seriously considering it,” she writes. The chapter ends there, and there’s no indication Facebook spread money around this way.    

Careless People paints former Facebook chief of operations Sheryl Sandberg (who left in 2022) as prone to bursts of anger and tone-deaf self-promotion, often at odds with the feminist principles she laid out in her hit corporate advice book Lean In, and unmoved by the plight of other women working in male-dominated Silicon Valley. More strangely, however, Wynn-Williams claims that Sandberg had a habit of crossing boundaries with her female subordinates. Not only did they have to assist on matters like book tours and public appearances that fell outside their job responsibilities, she writes, but they were sometimes instructed to join Sandberg in her bed on her private jet. On a flight back to the U.S. following the World Economic Forum in Davos, Switzerland, Wynn-Williams planned to spend the hours in the air working on a debrief as required by Sandberg, but the executive continued to insist — while wearing her pajamas — that she “come to bed” in the jet’s sole bedroom. Thinking that “it wouldn’t be right for a male COO to ask for this and it’s not right for a female one to,” Wynn-Williams kept refusing. She writes that Sandberg, irritated by this, said one more thing to her when the plane eventually landed in California: “You should have got into the bed.” On a later trip, Wynn-Williams claims she saw another of Sandberg’s female employees go into the bedroom with her at her request.

In 2016, Diego Dzodan, a Facebook vice president in Brazil, was arrested because WhatsApp, which the company owns, wouldn’t hand over messages related to a drug trafficking case. Wynn-Williams was horrified by the situation, but Zuckerberg — charmed by Dzodan’s allegiance to him in the face of possible prosecution by a nation with strict internet laws — wanted to celebrate the moment with a Facebook post, Wynn-Williams says. He drafted several versions, she writes, originally calling it a “heartwarming story” and claiming that Dzodan was acting in order to “protect our community,” while neglecting to mention that Facebook was shielding the privacy of an accused drug trafficking organization that had threatened to assassinate the judge in the case. She says that employees also warned a stubborn Zuckerberg that such a message would sabotage their legal defense of Dzodan, which was to tell the court that WhatsApp was a distinct company, and that a Facebook vice president can’t be held responsible for its decisions. Throughout internal discussions, Wynn-Williams observes, Zuckerberg “doesn’t seem to be worried about Diego in the slightest.” Ultimately, Dzodan was released within a day, and Zuckerberg never shared his “heartwarming” update on the vice president’s brief detainment.     

According to Wynn-Williams, Kaplan, her former boss, asked about her breastfeeding and the effects of the amniotic fluid embolism that nearly killed her after she gave birth to her second child, and deliberately drew attention to his habit of joining their virtual meetings from his bed. She alleges that he also commented on her looks and ground against her while dancing at a corporate event. Wynn-Williams further claims that he required her to do work during her second maternity leave and subjected her to a performance review the day she formally returned to the office, complaining she wasn’t “responsive enough” during her time recovering from the difficult birth and a coma due to extensive blood loss. During an unrelated internal investigation, Wynn-Williams put some of her complaints about Kaplan on the record with company lawyers, she writes, though when the possibility of a probe into Kaplan was floated, she agreed to drop it if he would stop making her uncomfortable. But he didn’t, she claims, and Kaplan effectively demoted her after this. She writes that a subsequent investigation into his behavior cleared him of any wrongdoing — then, at Wynn-Williams’ next performance review, she was summarily fired and escorted out of the office by a security guard, she writes. Responding to a request for comment from Rolling Stone on this matter, Meta claimed that the investigation into Wynn-Williams’ harassment claims was thorough and took longer than the average case, involving a review of all the documents she provided and 17 witness interviews.

Throughout Wynn-Williams’ tenure at Facebook, Zuckerberg was intent on expanding into China, where the platform was blocked. Their efforts, she writes, led to all kinds of gaffes, subterfuge, and queasy compromises. In 2015, Zuckerberg had the opportunity to shake hands with Chinese president Xi Jinping but was excluded from a closed-door meeting between Xi and other American tech CEOs. He posted a picture of himself and the back of Xi’s head anyway, making it appear that he was part of that meeting — and infuriating the Chinese government. (At a state dinner in the White House two days later, she writes, Xi declined Zuckerberg’s request to do him the honor of naming the child his wife was then carrying.) Later, Wynn-Williams was appalled at internal documents indicating the ways Facebook was evidently willing to comply with China’s censorship demands and requests for user data in exchange for being able to operate within the country someday: one memo cautioned that “Facebook employees will be responsible for user data responses that could lead to death, torture and incarceration.” In an incredibly clumsy move to penetrate the Chinese market, Facebook secretly released apps in the country through shell corporations without authorization, but supposedly with the tacit approval of China’s internet regulator. They were shut down after a New York Times story about the scheme.    

Careless People is unsparing in its account of how Donald Trump’s 2016 campaign gamed Facebook’s systems with misinformation and inflammatory content in the run-up to an upset election victory (and how Zuckerberg and Sandberg, in Wynn-Williams’ view, were impressed rather than alarmed by this). But the next year, Wynn-Williams writes, she discovered that the company was also courting advertisers with the option of targeting “thirteen-to-seventeen-year-olds across its platforms, including Instagram, during moments of psychological vulnerability when they feel ‘worthless,’ ‘insecure,’ ‘stressed,’ ‘defeated,’ ‘anxious,’ ‘stupid, ‘useless,’ and ‘like a failure,’” per a leaked document from a presentation to Australian brands. When the communications team considered a statement to the effect that Facebook wanted to “remedy” such practices, one member noted that they really weren’t doing anything to prevent such exploitation: users could be targeted based on emotional states, as well as racial and ethnic background. Facebook went as far as tracking when teen girls deleted selfies so that a company could “serve a beauty ad to them” right after, Wynn-Williams writes.