These are some of my favorite questions to ask speakers, friends, strangers and anyone in between. Some of them are pulled from favorite podcasts like Tim Ferris, David Kadavy and others and some I’ve thought of myself.
It’s a great idea to keep a note somewhere with a running list of your favorite questions in case you’re in a rut and just can’t think of something to ask people. Keep one of two of these in mind at events and see if you can get to more interesting conversations than constant small talk.
What are you most grateful for in your life recently?
Who was your favorite teacher?
Tell me about a fear that you overcame.
At what point is it wise to not follow the crowd?
What’s the craziest thing you’ve ever sold?
What is the most creative thing you’ve done recently?
What is the most admirable business you know of?
What is a book you’ve read recently that changed your perspective?
What’s a time when you’ve left money on the table?
What content do you consume?
What is a problem that not enough people care about?
What do you do when you’re in a funk and feeling down to get you out of that?
Have you gifted any particular books to people?
What are you trying to improve right now?
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