Conversation Starters

Wondering how to break the ice when you meet a new person at a networking event or are stuck beside someone on an airplane? Not sure how to take your conversation beyond the classic few “how are you/who are you” questions? Tuck a few of these intriguing, next-level questions in your back pocket, and you’ll be perfectly prepared:

  • How do you make decisions when the stakes are high?
  • What do you think is better – to be considered nice or to interesting?
  • A living legend. Who comes to mind for you?
  • If you won a huge sum of money, what would you no longer do?
  • Who is your worst imaginable marriage partner?
  • What do you consider to be the best work you’ve done?
  • Are the best five years of your career ahead of you or behind you?
  • Is there a piece of music you consider special? Why?
  • Who’s the most creative person you know?
  • Tell me about the first car you ever bought?
  • If you could travel to the past in a time machine, what advice would you give to the 12 year-old you?
  • Who has offered you the most useful career advice?
  • If you had to live somewhere else, where would you live?
  • What makes a person a good travelling companion?
  • Tell me about a decision you made that has had a major effect on your life?
  • What’s the most you’ve ever spent on a pair of shoes? (Did they end up being your favourites?)
  • What is your favorite way to spend a Saturday?
  • Did/do you have a nickname – what’s the story behind it? If you could create your own nickname what would it be?
  • If you could revisit one day in your life, which day would it be?
  • Would you rather be at the beach or in the mountains?
  • How do you think you would do on Survivor?
  • Have you ever won anything?
  • What’s the craziest thing you’ve ever eaten?
  • What is the origin of your last name?
  • Which four people would you want with you in a bomb shelter?
  • For which 2 accomplishments could an employer highly recommend you?
  • What would you improve about your school or university education?
  • Is your career playing out like you hoped it would?
  • If you had to save three things from your house (besides pets or people) what would you save?
  • If you could do anything you wanted to and money was not a factor, what would you do?
  • Where were you on September 11th 2001?
  • If you were to create a soundtrack for your life, what songs would you want on it?
  • Who do/have you worked with that you really respect?
  • If you could win a ‘life-time supply’ of anything what would you want it to be?
  • What do you “know now” that you wish you “knew then”?
  • If you had an extra hour every day what would you do with it?