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Great interview questions to ask

I have conducted hundreds of interviews over the years, and I've taken joy in helping students and clients become better at interviewing—asking good questions, but mostly listening. This one should be fun.

I realize the original intent may very well have been "great questions to ask in a job interview," but for me the idea of "interview" involves talking with someone for a radio piece, a news article, a blog post, a podcast interview—in other words, about fostering conversation. So that's the context. If it applies to job interviews, that works fine. After all, job interviews are just a more focused version of fostering a conversation so you can get to know someone.

Along similar lines, some of these are not technically questions, but they certainly are in the spirit of interviewing and drawing someone out.


    1. How did you get started with X?

    People love origin stories, but seldom think to ask. This is a great question to draw out a story.

    2. Tell me more about X.

    Not really a question, but one that tends to elicit some good material.

    3. If you could talk to yourself 10 years ago, what would you tell yourself?

    4. If you could talk to yourself 10 years from now, what would you like to know?

    5. Tell me a story about a person who deeply influenced you.

    6. Looking back, what's a decision that seemed small at the time that changed everything?

    7. If you were independently wealthy, what would you spend your time doing?

    8. What's your favorite memory from when you were getting started in your career?

    9. If you had not chosen the career path you did, what else might you have done?

    10. What would you like to be remembered for?

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