Release year: 2023

Author: Mark Schwartz

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Link to my handwritten notes


This book prompts us to grapple with uncomfortable yet essential questions that we often overlook or intentionally avoid. It’s a reminder that decisions on matters like privacy, productivity, profits, and agility shape our lives, especially in an era of digital transformation. While easy solutions are notably absent, the book offers a set of virtues that appear crucial for successful digital shifts within organizations. The author’s in-depth breakdown of the bureaucratic organization myth stands out to me, providing a compelling argument against embracing such outdated structures. I appreciated how this book made me realize that the definition of success evolves depending on the perspective you choose. It’s Systems Thinking all over again!

Félix rating:

⭐ Star quotes

  1. (p. 16) Since productivity no longer determines success, it can no longer be the measure of employee contribution.
  2. (p. 17) Overcoming recalcitrance is no longer the main function of management.
  3. (p. 19) The idea employee demonstrates contribution, rather than obedience.
  4. (p. 28) Consequentialism is not a good way to make ethical decisions in the digital world.
  5. (p. 30) The moral worth of an action can’t depend on its consequences, because those are uncertain. The goodness of an act can only depend on intention.
  6. (p. 45) What is “ethical” changes over time.
  7. (p. 78) Not everything that matters is measurable.
  8. (p. 86) There is no such thing as “trust by verify.” One verifies because of a lack of trust.
  9. (p. 90) Decentralizing authority allows employees to use their practical knowledge and their proximity to customers to innovate and make decisions. When we abstract away that practical knowledge into summary metrics and targets, we forego that advantage.
  10. (p. 105) Like euphemisms, bullshit and other forms of insincere communication, secrets create a space in which morally questionable behavior can flourish.
  11. (p. 112) It seems obvious that corporate criminals have some character flaw. They know (at least in the abstract) that what they are doing is wrong. The problem is institutional rather than individual, and blaming it on sociopathic behavior directs attention away from the more important organizational issues.
  12. (p. 123) When we encounter another individual truly as a person, not as an object for use, we become fully human.
  13. (p. 171) Our greatest glory is not in never falling, but in raising every time we fall.
  14. (p. 184) Valuing “success” is a way of denying the impact of uncertainty.
  15. (p. 193) A worker in a steel mill said: “Picasso can point to a painting. A writer can point to a book. What can I point to? Everybody should have something to point to.”
  16. (p. 195) The challenge for all of us who try to lead large-scale digital transformations in our enterprises is that we’re faced with conflicting imperatives:
    • Maximize returns for shareholders and satisfy social obligations
    • Empower teams and make sure they produce reliably
    • Adapt to changing circumstances and predict results + delivering on our predictions
    • Build deep relationships with customers and preserve their privacy and refrain from manipulating them inappropriately.
  17. (p. 196) The most critical ethical questions:
    • What do we want?
    • What does success look like?
    • What are we trying to optimize?