Asking Questions in the Negative — What Do You Regret? How Did You Fail?

When I asked my older friends a year ago what they did that they most regret or what they didn’t do that they most regret when they turned 18, I got a host of interesting answers. I believe the answers would have been different had I asked, “What are you most happy you did when you were 18?”

It’s a fascinating psychological exercise to elicit information through a negative phrasing.

Chris Yeh once excerpted from the book The Number which makes a similar point: asking a question in the negative reveals the most honest response:

[The author] describes his time with financial planner George Kinder, one of the pioneers of “life planning,” a discipline that tries to go beyond simply helping you figure out how much money you need, and into why you need it. The climax of his training occurs when he asks three simple questions:

1) Assume you have all the money you could ever need. What would you do with it? How would you live?

2) Your doctor discovers that you have a rare illness. You’ll feel perfectly fine, but you will die within 5 to 10 years. What would you do?

3) Your doctor tells you that you only have 24 hours to live. What did you miss? Who did you not get to be? What did you not get to do?

According to George Kinder, who asks these three questions, the first two questions produce long lists and concern material wants. The third question is almost always about something qualitative, and that is the answer that really matters.

I wonder if the same could be said for abstracting lessons from failure versus success. Which is a more effective story for imparting the importance of emotional intelligence and compassion: A CEO who is emotionally intelligent, warm, and successful at growing his business, or the CEO who’s an asshole, alienates employees, and fosters resentment in the organization? Although we tend to read books by the most successful people, I would argue learning the same lesson through a story about failure may be a more effective way to absorb and remember the lesson.

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