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What is the Most Illuminating Question I Can Ask Someone to Gain Insight About Them?

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What is the Most Illuminating Question I Can Ask Someone to Gain Insight About Them?

This was an interesting discussion on Quora recently that centered on determining what single question could be asked of anyone you met in order to gain insight from them. There were a number of different answers posted, ranging from queries about how the person’s life would change if they were suddenly homeless, to how they would choose to live their lives if they were suddenly independently wealthy.

Here are just a few of the questions that people came up with; ones that they believed would give them invaluable insight into another’s personality and life in general:

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  • “What’s the most unexpected thing you’ve learned along the way?”
  • “What is the best piece of advice you have been given?”
  • “How will you make this world a better place than when you came into it?”
  • “What would you do if you knew you could not fail?”
  • “What is the craziest belief (the one that fewest educated people will agree with) that you hold? Why do you believe it?”

Asking people what they’ve learned as part of their life’s journey can give you invaluable insight about who they are and where they’ve been: you can tell whether they’ve been through hardships and gained wisdom and insight from them, or whether they’ve become embittered by what they believed to be injustices.

“If You Only Had One ____ Left to Live…”

There’s another question that wasn’t on the Quora list, but might be rather illuminating when speaking to another:

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“If you only had one year/month/week/day to live, how would you spend your time?”

Most of us put things off for later or make plans for the future with the assumption that we have all the time in the world, but if we were suddenly faced with a deadline (no pun intended) for our imminent passing, what would we do? Is the average person so content with their life as it is that they’d continue doing exactly what they’re doing until they drop off? Would they quit their job and go spend their last days at a petting zoo? Or perhaps go to an ashram or convent to attune spiritually before they pass?

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You’ll be able to glean a fair amount about the one you’re talking to by how they answer this question.

Someone who’s living a very jet-setting, high-profile life in the downtown core of a big city might tell you that they’d drop everything and spend their last days catching up on reading and hanging out with their dog, or they might say that they’ll continue working at their job until they fall down dead. What would that tell you in either case? In the first, you might intuit that deep down, they’re very home-loving, peaceful people who are putting on a good game face in a career that isn’t ideal for them. In the second, you may learn that this person absolutely loves what they do and would be happiest keeling over in the middle of a power lunch if it meant they could get one last contract signed.

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That professor of yours who’s normally a bit aloof might take the time to write letters to old friends and acquaintances to say his farewells, and the elderly lady down the road might empty her savings account for a wild, drunken Caribbean “goodbye world!”-fest. Some people are open books and would do exactly as you’d expect if they knew their number was up soon, but I’m guessing that in most cases, you’d be a bit surprised at what lurks inside people’s hearts, tucked away from societal expectations.

In addition to giving you invaluable insight about them, asking this question can actually have some startling effects on the one being asked as well. It’s possible that they hadn’t considered such a possibility: people generally don’t like to think about death, but really taking into consideration the fact that we aren’t going to be around forever can encourage some rather significant life changes, especially in those who aren’t exactly living their dreams.

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Many would argue that there is no one, single question that would work for everyone you encounter, and that queries of such depth and magnitude should be tailored to suit the individual instead of generalized like those mentioned above.

What do you think?

More by this author

Catherine Winter

Catherine is a wordsmith covering lifestyle tips on Lifehack.

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