C. Invite Others to Question Your Thinking

7. Learn something new from each person you meet. Everyone knows more than you about something. Ask people what they’ve been rethinking lately, or start a conversation about times you’ve changed your mind in the past year.

8. Build a challenge network, not just a support network. It’s helpful to have cheerleaders encouraging you, but you also need critics to challenge you. Who are your most thoughtful critics? Once you’ve identified them, invite them to question your thinking. To make sure they know you’re open to dissenting views, tell them why you respect their pushback—and where they usually add the most value.

9. Don’t shy away from constructive conflict. Disagreements don’t have to be disagreeable. Although relationship conflict is usually counterproductive, task conflict can help you think again. Try framing disagreement as a debate: people are more likely to approach it intellectually and less likely to take it personally.

II. INTERPERSONAL RETHINKING

A. Ask Better Questions

10. Practice the art of persuasive listening. When we’re trying to open other people’s minds, we can frequently accomplish more by listening than by talking. How can you show an interest in helping people crystallize their own views and uncover their own reasons for change? A good way to start is to increase your question-to-statement ratio.

11. Question how rather than why. When people describe why they hold extreme views, they often intensify their commitment and double down. When they try to explain how they would make their views a reality, they often realize the limits of their understanding and start to temper some of their opinions.

12. Ask “What evidence would change your mind?” You can’t bully someone into agreeing with you. It’s often more effective to inquire about what would open their minds, and then see if you can convince them on their own terms.

13. Ask how people originally formed an opinion. Many of our opinions, like our stereotypes, are arbitrary; we’ve developed them without rigorous data or deep reflection. To help people reevaluate, prompt them to consider how they’d believe different things if they’d been born at a different time or in a different place.

B. Approach Disagreements as Dances, Not Battles

14. Acknowledge common ground. A debate is like a dance, not a war. Admitting points of convergence doesn’t make you weaker—it shows that you’re willing to negotiate about what’s true, and it motivates the other side to consider your point of view.

15. Remember that less is often more. If you pile on too many different reasons to support your case, it can make your audiences defensive—and cause them to reject your entire argument based on its least compelling points. Instead of diluting your argument, lead with a few of your strongest points.

16. Reinforce freedom of choice. Sometimes people resist not because they’re dismissing the argument but because they’re rejecting the feeling of their behavior being controlled. It helps to respect their autonomy by reminding them that it’s up to them to choose what they believe.

17. Have a conversation about the conversation. If emotions are running hot, try redirecting the discussion to the process. Like the expert negotiators who comment on their feelings and test their understanding of the other side’s feelings, you can sometimes make progress by expressing your disappointment or frustration and asking people if they share it.

III. COLLECTIVE RETHINKING

A. Have More Nuanced Conversations

18. Complexify contentious topics. There are more than two sides to every story. Instead of treating polarizing issues like two sides of a coin, look at them through the many lenses of a prism. Seeing the shades of gray can make us more open.

19. Don’t shy away from caveats and contingencies. Acknowledging competing claims and conflicting results doesn’t sacrifice interest or credibility. It’s an effective way to engage audiences while encouraging them to stay curious.

20. Expand your emotional range. You don’t have to eliminate frustration or even indignation to have a productive conversation. You just need to mix in a broader set of emotions along with them—you might try showing some curiosity or even admitting confusion or ambivalence.

B. Teach Kids to Think Again

21. Have a weekly myth-busting discussion at dinner. It’s easier to debunk false beliefs at an early age, and it’s a great way to teach kids to become comfortable with rethinking. Pick a different topic each week—one day it might be dinosaurs, the next it could be outer space—and rotate responsibility around the family for bringing a myth for discussion.

22. Invite kids to do multiple drafts and seek feedback from others. Creating different versions of a drawing or a story can encourage kids to learn the value of revising their ideas. Getting input from others can also help them to continue evolving their standards. They might learn to embrace confusion—and to stop expecting perfection on the first try.

23. Stop asking kids what they want to be when they grow up. They don’t have to define themselves in terms of a career. A single identity can close the door to alternatives. Instead of trying to narrow their options, help them broaden their possibilities. They don’t have to be one thing—they can do many things.

C. Create Learning Organizations

24. Abandon best practices. Best practices suggest that the ideal routines are already in place. If we want people to keep rethinking the way they work, we might be better off adopting process accountability and continually striving for better practices.

25. Establish psychological safety. In learning cultures, people feel confident that they can question and challenge the status quo without being punished. Psychological safety often starts with leaders role-modeling humility.

26. Keep a rethinking scorecard. Don’t evaluate decisions based only on the results; track how thoroughly different options are considered in the process. A bad process with a good outcome is luck. A good process with a bad outcome might be a smart experiment.

D. Stay Open to Rethinking Your Future

27. Throw out the ten-year plan. What interested you last year might bore you this year—and what confused you yesterday might become exciting tomorrow. Passions are developed, not just discovered. Planning just one step ahead can keep you open to rethinking.

28. Rethink your actions, not just your surroundings. Chasing happiness can chase it away. Trading one set of circumstances for another isn’t always enough. Joy can wax and wane, but meaning is more likely to last. Building a sense of purpose often starts with taking actions to enhance your learning or your contribution to others.

29. Schedule a life checkup. It’s easy to get caught in escalation of commitment to an unfulfilling path. Just as you schedule health checkups with your doctor, it’s worth having a life checkup on your calendar once or twice a year. It’s a way to assess how much you’re learning, how your beliefs and goals are evolving, and whether your next steps warrant some rethinking.

30. Make time to think again. When I looked at my calendar, I noticed that it was mostly full of doing. I set a goal of spending an hour a day thinking and learning. Now I’ve decided to go further: I’m scheduling a weekly time for rethinking and unlearning. I reach out to my challenge network and ask what ideas and opinions they think I should be reconsidering. Recently, my wife, Allison, told me that I need to rethink the way I pronounce the word mayonnaise.

ACKNOWLEDGMENTS

The expression of gratitude is something that probably needs less rethinking and more doing. I want to start by commending literary agent extraordinaire Richard Pine for inspiring me to rethink my audience and continue broadening my lens beyond work, and editor par excellence Rick Kot for believing in and developing the potential of these ideas. As always, it was a dream to work with the two of them, and they offered the ideal blend of challenge and support.

The accuracy of this book was enhanced by the meticulous work of two professional fact-checkers. Paul Durbin applied his eagle eye to every sentence, working with remarkable thoroughness and alacrity. Andy Young carefully reviewed every page and followed up with a number of key sources.