Book Club Discussion Questions for Careless People by Sarah Wynn-Williams

1. Careless People begins with a quote from The Great Gatsby. How do you think this sets the stage for the rest of the book? Did the epigraph have an impact on how you approached reading what followed?
2. Sarah Wynn-Williams writes that her career at Facebook "started as a hopeful comedy and ended in darkness and regret." What did you think of this statement? Are there examples of each extreme that stand out to you?
3. The author began considering working for Facebook in 2009, "in those innocent days when it still was possible to be hopeful about the internet." What do you remember about your first experiences of the internet or social media? What has changed over the years, and what hasn't?
4. As a teenager, Sarah is attacked by a shark. Why do you suppose she includes this story in the book? What do you think this says about her?
5. While still working at the U.N., the author comes to the realization that Facebook "would change the course of human events" and she was "desperate to be a part of it." Why do you think she was so driven to join the company? Would you have been as persistent, had you been in her shoes?
6. Why do you think Sarah could see Facebook's potential while those intimately involved with it seemed oblivious to it?
7. How did you feel about each of the company's principals (Mark, Sheryl, Elliot, and later, Joel)? Did your opinion of any of them change over the course of the book, and if so, how?
8. Early on, the author writes that Mark's "focus is engineering, and his disregard for politics is a point of pride." Did this surprise you? Would Facebook's trajectory been any different, do you suppose, if someone in power had recognized the political implications sooner?
9. What aspects of Facebook's culture did you find surprising in the first few chapters of the book? What changed by the end of Sarah's tenure there, and what didn't?
10. Sheryl keeps a brutal schedule, and as her employee Sarah feels she has "no choice but to adapt to her routine, working with crushing intensity." Later, Sheryl tells her this is by design, that "staffers should be given too much to do because it's best if no one has spare time." What did you think of this? Do you believe this type of working atmosphere is generally more common today, or less?
11. What parts of Sarah's experience at Facebook would you have enjoyed? What parts did you find horrifying?
12. Sarah talks many times about quitting Facebook but never does. Why do you suppose she stays? What aspect of working for the company would you have found the most challenging? What would have been the "last straw" for you, had you been in Sarah's shoes?
13. Do you feel any part of Sarah's experiences would have been different had she been born and raised in America rather than New Zealand?
14. Mark states that "Facebook was built to accomplish a social mission – to make the world more open and connected." Do you feel he succeeded? What are the benefits of a connected world, and what are the drawbacks, in your opinion?
15. There are posters all over the Facebook offices that say, "Move fast and break things." What message do you think they're trying to convey to their staff? In what ways is this sentiment borne out at Facebook? Do you consider this an appropriate corporate strategy for a tech company? Why or why not?
16. Based on Sarah's account, do you feel Facebook should be more regulated, and if so, by whom and in what ways? What changes would you enact at the company, if you had the ability?
17. Sarah writes that "The expectation at Facebook is that mothering is invisible," and later, that Mark might not be present for the birth of his first child because "something more important might come up." What do you think of the company's attitude toward parenthood? In what ways did Sarah try to live up to their expectations? Did any of her actions surprise you?
18. Mark is angry with the implication that Facebook helped Donald Trump get elected. Why do you think the head of a "business premised on the notion that it can influence the brand of toothpaste you buy" has so much trouble accepting his company's role in the election? Do you believe Facebook does, indeed, influence elections and if so, in what ways?
19. Facebook touts a bare-bones internet service called Internet.org (later Free Basics), with the goal of providing some form of internet to everyone, even those in remote areas. What did you think of this initiative? Do you think having the internet available is a right, and is Facebook's version "better than nothing"?
20. Overall, what did you think of Careless People?

Unless otherwise stated, this discussion guide is reprinted with the permission of Flatiron Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.