101 Good Questions to Ask

You are given the opportunity to give your 18-year-old self some career advice: what would you say?
What’s wrong but sounds right?
Do you think that children born today will have better or worse lives than their parents?
Before making a telephone call, do you ever rehearse what you are going to say? Why?
If, you were invisible for a day, what would you do?
If money wasn't a factor, how would you spend the rest of your life?
What's your biggest irrational fear?
What is your favourite thing about yourself?
What's the weirdest dream you've ever had?
What’s something that will always be in fashion, no matter how much time passes?
How do you decide who to vote for?
What is something you are obsessed with?
What is something that really annoys you but doesn’t bother most people?
Who would be the worst person to be stuck in an elevator with?
If you could bring back one TV show that ended, which one would you bring back?
What’s the strangest movie you have ever seen?
What is the longest book you have read?
What book has had the biggest effect on the modern world?
If you opened a restaurant, what kind of food would you serve?
Where is the most relaxing place you have been?
What was the most overhyped place you’ve travelled to?
What’s the worst thing about travelling?
What was the best invention of the last 50 years?
What problems will technology solve in the next 10 years?
What technology from a science fiction movie would you most like to have?
What do you think the next big technological advance will be?
What is the craziest thing you want to achieve?
Time freezes for everyone but you for one day. What do you do?
A portal to another world opens in front of you. You don’t know how long it will stay open or if you’ll be able to get back after you go through. What do you do?
You have to relive one day of your life forever. Which day do you choose?
Will religion ever become obsolete?
Would you want to know you are going to die beforehand or die suddenly without warning?
Is it better for a person to have a broad knowledge base or a deep knowledge base?
How much does language affect our thinking?
Why are humans so confident in beliefs that can’t be proven?
What languages do you wish you could speak?
What country is the strangest?
What habit do you have now that you wish you started much earlier?
What’s the most annoying noise?
What trend are you tired of?
What’s the most boring sport?
What’s legal now, but probably won’t be in 25 years?
What’s the best and worst thing about the country you are from?
Would you rather live your entire life in a virtual reality where all your wishes are granted or in the real world?
What skill would you like to master?
If you could make a 20-second phone call to yourself at any point in your life present or future, when would you call and what would you say?
What is more appealing to you: to be seduced or to do the seducing?
Which parts of your body are you most ashamed of?
If you partner was magically offered a chance to change something about you, what do you think they would pick?
When you get really angry, are you more like your mother, father or someone else?
How could older people be valued more?
If you were in a village and had to choose between a good meal and bad hotel or bad meal and a good hotel, which would you prefer?
If you could only have one medium, which one would you choose: art, film, literature, music.
Describe a piece of art that you really like and why?
Why is art so expensive?
Of the people you spend time with, who brings out your best qualities?
If you could own any one piece of art, what would it be?
Have you and your partner or friends ever argued about taste?
What's the kindest thing anyone's done for you?
What are your happiest memories of your parents?
What are the best things you owe your parents?
Do you feel happier spending or saving?
Would you be happy to tell your friends how much you earn?
Would you prefer to be a psychoanalyst or a doctor?
If you have to choose between a happy home life and a mediocre career, or a successful career and mediocre home life, which would you choose?
Who has offered you the most useful career advice?
What is the most surprising conversation you've ever had?
If you knew you only had one year to live from now, how would you spend the next 12 months?
If you had to live somewhere else, where would you live?
What makes a person a good travelling companion?
Have you ever travelled on your own?
Are you more attracted to a nomadic or settled life?
What makes you most stressed?
When do you feel shy?
In what respects are you still the same person you were as a child?
Is there anything you regret not doing due to fear?
Do you have a technique for keeping calm?
If you had to write a book, what would it be about?
Are you where you wanted to be at this stage in your life?
Who is your biggest fan?
Who or what might have stopped you from realising your full potential?
If you had married your first boy/girlfriend, what might your life be like now?
If life were 200 years long, what careers would you want to have had?
My ideal obituary would explain that I...
The type of people I am least suited to working with is...
If all jobs were paid exactly the same, what job would you be attracted to?
If you could take two years out to learn a new skill, what would it be?
What's the best piece of travel advice you've received?
What was the strangest thing you ate?
Do you prefer tourist attractions or living like the locals?
If you could witness any event of the past, present, or future, what would it be?
What professional situations would you consider both desirable and yet too stressful for you?
If you don't worry about failure, what might you try doing?
The thing that really holds me back in my work is....
You are tasked with making the world more beautiful. Where do you start?
If you have $10M to set up a business, what would you do?
The talent I would most like to have is...
Is it more satisfying to lead or to belong to a team?
Failure was defined in my family as...
If there were no consequences, who at work would you like to have a relationship with?
In what ways do you and your partner have different ideas of success?