What’s the most important question you should be asking?



I don’t spend nearly enough time on Quora. There’s some great stuff there, including a crowdsourced list of thoughts on “What is the single most illuminating question I can ask someone?

Some of my favorites from the answer wiki:

  • “What’s the most unexpected thing you’ve learned along the way?”
  • “If you could call yourself five years ago and had 30 seconds, what would you say?”
  • What would you do with your time if you could afford to quit your job?
  • Someone gets a text message from you, and for whatever reason they’re not sure it’s actually you. They’re worried that someone may have stolen your phone. What could they ask to make sure it’s really you?
  • What is the craziest belief (the one that fewest educated people will agree with) that you hold?  Why do you believe it?

Questions have power that statements don’t.

The Socratic method really does help you learn. Rhetorical questions are more persuasive than statements. Hypothetical questions can be used to manipulate you.

What else can questions do?


Questions connect you with others

Researcher Arthur Aron (author of Handbook of Closeness and Intimacy) has shown that which questions you ask can dramatically affect whether you connect with someone and how deeply.

Via Snoop: What Your Stuff Says About You:

Arthur Aron, a psychologist at the State University of New York at Stony Brook, is interested in how people form romantic relationships, and he’s come up with an ingenious way of taking men and women who have never met before and making them feel close to one another. Given that he has just an hour or so to create the intimacy levels that typically take weeks, months, or years to form, he accelerated the getting-to-know-you process through a set of thirty-six questions crafted to take the participants rapidly from level one in McAdams’s system to level two. 

But how effective can this be really? In under an hour it can create a connection stronger than a lifelong friendship.

Via Click: The Magic of Instant Connections:

What he found was striking. The intensity of the dialogue partners’ bond at the end of the forty-five-minute vulnerability interaction was rated as closer than the closest relationship in the lives of 30 percent of similar students. In other words, the instant connections were more powerful than many long-term, even lifelong relationships.

So what are some of the questions?

1. Given the choice of anyone in the world, whom would you want as a dinner guest?

2. Before making a telephone call, do you ever rehearse what you are going to say? Why?

3. What would constitute a “perfect” day for you?

4. For what in your life do you feel most grateful?

5. If you could change anything about the way you were raised, what would it be?

6. If you could wake up tomorrow having gained any one quality or ability, what would it be?

7. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

8. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

9. What, if anything, is too serious to be joked about?

10. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

 (More of Aron’s questions are here.)


Questions connect you with yourself

Saying positive statements is supposed to increase your self-esteem and confidence. “You can do it!”

But research is showing that asking yourself if you can do it might be an even better approach. Dan Pink explains in his book To Sell Is Human: The Surprising Truth About Moving Others:

The researchers instructed the first group to ask themselves whether they would solve the puzzles — and the second group to tell themselves that they would solve the puzzles. On average, the self-questioning group solved nearly 50 percent more puzzles than the self-affirming group. 

Why does this work? Dan explained in my interview with him:

…before an encounter, get over that idea that you should say “You can do it,”… Instead, look at this research that I write about, about interrogative self-talk and instead ask yourself, “Can you do this?” When you ask yourself something, you respond actively, and in the active response are the strategies, tactics, the mechanisms for getting it done.

I had to do a big interview. I thought it through, but instead of saying on the morning of it, “You can do this,” I actually used this. I said, “Can you do this?” I said, “Can I do this? Well, yeah, because I find this stuff really interesting, and I researched the hell out of it, and I think I can talk well about any aspect of it.” “Can you do this?” “Well, I actually went and listened to previous interviews that this guy had done, and so I have a good sense of his style.” “Can you do this?” “Yeah, I have a good sense of what might be some of the tougher questions, and I have fairly good answers for those.” So what I’m doing is, I’m kind of rehearsing, and it’s much more muscular than simply going in there and saying “Oh, you’re awesome, Dan, you’re awesome, you’re just fantastic.” You know? I think that moving from “I can do it” to “Can I do this?” is really, really powerful. It’s a more muscular way of getting prepared for something. 

Questions are powerful. As Picasso once said:

Computers are useless. They only give you answers.

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