25 Discussion Questions for David and Goliath by Malcolm Gladwell (With Analysis) | Chapterly Blog
Quick Answer: The most useful David and Goliath discussion questions test Gladwell's central reframing — that we systematically misidentify who holds the advantage — against his actual case studies (the biblical duel, dyslexic entrepreneurs, the London Blitz, Northern Ireland). The 25 questions below are organized by theme and built for book clubs, leadership programs, and college courses that want to weigh Gladwell's "advantages of disadvantage" thesis against the survivorship bias his narrative selection invites. Malcolm Gladwell's David and Goliath challenges conventional wisdom about what it means to be an underdog and what it means to have an advantage. These David and Goliath discussion questions explore whether disadvantages can become strengths, whether advantages contain hidden costs, and how our understanding of power dynamics is systematically wrong. Whether you are in a book club, a business leadership program, or a college course, these questions will push you to rethink your assumptions about success, struggle, and resilience. Published in 2013, the book reinterprets the biblical story of David and Goliath as a tale of a nimble fighter exploiting a lumbering opponent's weaknesses — not a miracle, but a strategic mismatch. From there, Gladwell explores dyslexia as a hidden advantage for entrepreneurs, the surprising...