Reading Group Guide

In her mid-twenties, at the height of tech-industry idealism, Anna Wiener—restless, and looking for meaning in her work, like any good millennial—left a job in book publishing for the promise of the new digital economy. She moved from New York to San Francisco, where she landed at a big-data startup in the heart of the Silicon Valley bubble: a world of surreal extravagance, dubious success, and fresh-faced entrepreneurs hell-bent on domination, glory, and, of course, progress.

Anna arrived during a massive cultural shift, as the tech industry rapidly transformed into a locus of wealth and power rivaling Wall Street. But amid the company ski vacations and in-office speakeasies, boyish camaraderie and ride-or-die corporate fealty, a new Silicon Valley began to emerge—one in far over its head, and enriching itself at the expense of the idyllic future it claimed to be building.

Part coming-of-age story, part portrait of an already bygone era, Uncanny Valley is a rare first-person glimpse into high-flying, reckless startup culture at a time of unchecked ambition, unregulated surveillance, wild fortune, and accelerating political power. With wit, candor, and heart, Anna deftly charts the tech industry's shift from self-appointed world savior to democracy-endangering liability, alongside a personal narrative of aspiration, ambivalence, and disillusionment.

Unsparing and incisive, Uncanny Valley is a cautionary tale, and a revelatory interrogation of a world reckoning with consequences its unwitting designers are only beginning to understand.

1. Why does Anna Wiener leave New York and a career in publishing? What are her first impressions of San Francisco and the people who live and work there? What qualifications does she bring to the job in customer support at a data analytics startup? What are her goals?

2. What is the “uncanny valley”? Why does Wiener choose this term for the title of her memoir? What are examples of her experiences that fit the definition?

3. What kind of manager is the CEO of the analytics startup? How does he treat Wiener? How do his employees treat him? What signals does he send with his weekly all-hands meetings? With his insistence on the slogan “Down for the Cause”? What message might the CEO be meaning to send by firing Noah, one of his earliest and most talented hires?

4. Wiener writes, “What was anyone ever talking about? People said things like ‘coexecute’ and ‘upleveling’; they used ‘ask’ and ‘attach’ and ‘fail’ as nouns. They joked about ‘adulting.’” How does the language of a workplace reveal its culture and attitudes? How has the language and business culture of Silicon Valley spread?

5. Late one Friday afternoon, Wiener is summoned into a surprise meeting with the CEO of the analytics startup. He questions her abilities and loyalty and tells her, “I don’t think we have the same values. I don’t even know what your values are.” Though it seems like she will be fired, she is given a promotion soon after the meeting. What might have been the CEO’s motive? What are his values? How does Wiener come to realize what she values? Can it be said that there are common values among the workers of Silicon Valley?

6. At a company where most employees work remotely, Wiener often feels isolated or lonely. How does she cope with this? How is the life she lives online representative of the impact of the internet and social networks on all our lives? How have relationships, socializing, learning, creating, shopping, et cetera, been changed?

7. What is a meritocracy? What are its benefits and pitfalls? As Wiener explains to a New York friend why she stays at her job, she realizes that there are some things that “Silicon Valley got right.” What does she find satisfying and fun about her work?

8. What is the new hire Danilo’s vision for technology? Why is it significant? When the secretary of Housing and Urban Development visits the open-source startup to discuss broadening access to home computers and closing the digital literacy gap, Danilo introduces his presentation by saying, “The internet is an accelerant for growth and a dissolver of class walls. . . . Most of all, it is the ticket to twenty-first century prosperity.” Is there evidence that this is true at every level of society?

9. During Wiener’s time with the analytics startup, an NSA contractor leaks information that shows the United States government has been spying on private citizens. How does her employer respond to this? Why does her manager tell her, “We’re the good guys?” What happened during the 2016 presidential campaign that brought big data’s flaws and its power into the open?

10. What is it like for Wiener and other women working at mostly male tech companies? How do her employers respond when Wiener asks for higher pay and more equity? When she reported blatant sexual harassment? How do men and women differ in their explanations of why there aren’t more women working in Silicon Valley startups? What attributes might women bring to these workplaces that would improve both profits and quality of life?

11. Who are the people who support Wiener or influence her decisions? How do her friendships with men, as well as her relationship with Ian, help her become acclimated to Silicon Valley and the culture of tech startups? What does she learn from Noah? From Patrick?

12. How is work-life balance defined and practiced at the open-source startup? What are the mandatory parties, trips, and other, sometimes silly, team-building and social events meant to accomplish? How is freedom defined and achieved? Is the corporate environment at each of Wiener’s companies more culture or cult?

13. What do many tech startups have in common with regard to their origins? Who are the founders? How are they initially funded? Who are early hires and what incentives are they offered? How do these companies respond to setbacks? To success? To critical issues like diversity, privacy, security, and abuse of their platforms?

14. What have been the consequences of “scale” for the corporations of Silicon Valley? For the city of San Francisco and its long time residents? What solutions have been proposed for problems with housing and homelessness, transportation, and so on, caused by explosive growth and imbalance of wealth?

15. In 2018, after five years in Silicon Valley, Wiener exercises her stock options and resigns from the open-source startup. What is the basis for this decision? How does the aftermath of the 2016 election affect her and the corporations of Silicon Valley? As she reflects on her time spent working at tech startups, what does she see as the highs and lows? What are issues she believes need to be addressed? What might she see as the future of silicon valley as represented by her former CEO, her coworkers, and her managers?