- “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 is the best piece of advice you have been given?
- What is the first moment you remember in your Life?
- What is the best question anyone has ever asked you? …and how did you answer?
How You Would Spend Your Time
- “On a scale of 1 to 10, how happy are you with your life?” Then, after I answered, I was asked, “What would make it a 10?”
- “How will you make this world a better place than when you came into it?”
- “When you die, what do you want to be remembered for?”
- What would you do with your time if you could afford to quit your job?
- If all jobs paid the same, what would you be doing?
- What would you do if you knew you could not fail?
- Are you doing what you thought you would be doing when you were growing up?
- What would you change in your life now if you wanted the answer to this question:”What is your greatest regret?” to be “I have no great regrets?”
About You
- 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 music do you listen to?
- What is the craziest belief (the one that fewest educated people will agree with) that you hold? Why do you believe it?
- Make a request where the “right thing to do” is for the other person to say no to you.
- Are you lucky?
- What would you do if you were homeless?
“How will you make this world a better place than when you came into it?”
or similarly, in the same spirit,
“When you die, what do you want to be remembered for?”
I’ve found that, in general, a person can only answer these questions well if:
- they’ve done a fair amount of self-reflection
- they’re reasonably good at long-term thought/planning
- they have a good assessment of their current skill-set, what skills they want, and how they can use the former to help achieve the latter
- they have self-confidence
- they are aware of their mortality and, rather than fearing it, are inspired to do as much good as possible
What is the first moment you remember in your Life?
What are 3 qualities that you take most pride in in yourself?
If you were to be exiled to a deserted island (presumably this island has nothing other than basic survival items) by yourself and were allowed one comfort item, what would that item be?
What is the last thing that you have seen/heard/experienced that has inspired you?
Do you have a role model right now, and why is that person your role model?
What are you most afraid of, amongst the 7 deadly fears?
– Most people don’t know what the 7 deadly fears are, so I often phrase this question as “What is worse, rejection, inadequacy, guilt, or whatever else you can think of?”
Rank the love languages for a) how you love to receive, and b) how you give.
What is the funniest thing that you’ve ever watched?
– Some people say chick flicks, some say The Office type shows, for me the Tina Fey spoof with Sarah Palin in 2008 takes the cake. You get the point.
If you go into a bookstore, what is the first section that you will go to?
What engages you intellectually?
Someone just told you “you are awesome”. What just transpired?
What drives you? If there ever come a point where you commit suicide (touch wood), presumably because you have lost all hope and drive to live, why would that be?
What would keep you up at night?
What is the most misunderstood trait/belief about you?
10 years later, you are the happiest person in the world. What could have happened in between those 10 years?
When was the last time you cried, and why?
What is your proudest moment in your life thus far?
– I get answers ranging from career accomplishments, to small things which do their family proud, to encounters with personal growth, etc.
What would be one skill that you would want to learn if you could master it in 1 hour?
Delusions of Adequacy 