How to Interview Someone by Asking Memorable Questions

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So far this year, I’ve been asked to be a guest on over 30 podcasts, and been interviewed for random blogs about 50 times or so. I’m at the point now where I can tell within the first 30 seconds of the podcast, or the first line of the written interview, whether it’s going to be a good one or not, and the number one way I can tell? It comes down to the questions the interviewer asks.

Here’s the thing – If I’m taking the time out of my schedule to sit with you on a live podcast, or answer a dozen or so interview questions by email, there’s only one thing I ask of you in return:

Do your homework, so you can ask me really great questions.

I can’t tell you how frustrating it is to agree to do an interview and then receive a list of questions where the first one is “So what do you do?” Are you kidding me? Come on. 

​If you really want to interview me and you haven’t taken five seconds to Google me, why are we wasting our time? And I’m not saying that like I’m all that and a bag of chips, either. Rather, wouldn’t you agree that the more you know about me before we start, the more compelling our talk will be?

Here are a few tips on how to make our interview, your blog post or podcast, the best it can be:

Ask me unique, relevant questions. There’s nothing worse than being given a list of questions that you know have been copied and pasted a million times before. Things like “What’s your website?” or “What does The Geek Factory, Inc. do?” Right off the bat, this is going to make me wonder why I’m wasting my time. If you’re asking every interviewee the same questions, you’re really cheating your audience out of quality content (and probably don’t deserve an audience in the first place.)

Your homework determines the flow of the conversation. If your first question on the podcast is “Peter, back in 2010, you sold HARO. Tell me your feelings about saying goodbye to something on which you’d worked so hard,” then I know you’ve done your homework, and I’m going to open up to you. If your first question is “so tell us something about you,” I’m going to respond with my standard quote from The Fifth Element. “I am a meat popsicle.

The best questions play off my previous answers. If I answer a question honestly, and open myself up to you, the best thing you can do is to keep that conversation going, by asking me a follow-up question, or at least using my answer to frame your next question. The worst thing you can do is go “Uh huh, sure, So, here’s my next question.” That simply tells me that you’re waiting for me to stop talking so you can run through the motions. The best interviews are free-flowing conversations, not staccato questions and answers.

In the end, the goal is to teach your audience something they didn’t know before, or even better, something they didn’t know they didn’t know. The best way to do that is to ask really pointed questions that lead to a bigger question overall. Before we start, ask yourself – What’s the end game here? What do I want my audience to learn? Once you get that, work backwards to create the questions.

A great example of doing this well is the video interview below that I did with Behind the Brand several months ago. It’s worth a watch.

Anything else that makes a great interview? I’d love to hear about it in the comments below. As always, thanks for reading!

Join the discussion 19 Comments

  • Molly Jo Rosen says:

    This is true not just of media interviews. As someone on the job hunt, nothing is worse than an HR manager or a recruiter opening the interview with “so you’ve worked where…?” I know hiring is like a cattle call casting, so I don’t expect them to have Googled me like – say – a date would, but a little reading over my LinkedIn profile before I walk in the door will save us all a lot of wasted time. And we interviewees also have the same responsibility to know the company / people we’re lucky enough to get an audience with: you look like a rockstar for taking five whole seconds to add the personal touch of knowing where someone went to school or that the company just landed a round of funding.

  • Molly Jo Rosen says:

    This is true not just of media interviews. As someone on the job hunt, nothing is worse than an HR manager or a recruiter opening the interview with “so you’ve worked where…?” I know hiring is like a cattle call casting, so I don’t expect them to have Googled me like – say – a date would, but a little reading over my LinkedIn profile before I walk in the door will save us all a lot of wasted time. And we interviewees also have the same responsibility to know the company / people we’re lucky enough to get an audience with: you look like a rockstar for taking five whole seconds to add the personal touch of knowing where someone went to school or that the company just landed a round of funding.

  • Molly Jo Rosen says:

    This is true not just of media interviews. As someone on the job hunt, nothing is worse than an HR manager or a recruiter opening the interview with “so you’ve worked where…?” I know hiring is like a cattle call casting, so I don’t expect them to have Googled me like – say – a date would, but a little reading over my LinkedIn profile before I walk in the door will save us all a lot of wasted time. And we interviewees also have the same responsibility to know the company / people we’re lucky enough to get an audience with: you look like a rockstar for taking five whole seconds to add the personal touch of knowing where someone went to school or that the company just landed a round of funding.

  • tarandfeatherthecrooks says:

    “Running in Central Park….Lumbering…” Ha Ha Ha! Great interview. Thanks

  • tarandfeatherthecrooks says:

    “Running in Central Park….Lumbering…” Ha Ha Ha! Great interview. Thanks

  • tarandfeatherthecrooks says:

    “Running in Central Park….Lumbering…” Ha Ha Ha! Great interview. Thanks

  • tarandfeatherthecrooks says:

    “Running in Central Park….Lumbering…” Ha Ha Ha! Great interview. Thanks

  • tarandfeatherthecrooks says:

    “Running in Central Park….Lumbering…” Ha Ha Ha! Great interview. Thanks

  • That moment where he is contemplating your questions and you need a fainting couch hoping HIS blog wasn’t inspired by YOUR questions. :/

  • That moment where he is contemplating your questions and you need a fainting couch hoping HIS blog wasn’t inspired by YOUR questions. :/

  • That moment where he is contemplating your questions and you need a fainting couch hoping HIS blog wasn’t inspired by YOUR questions. :/

  • Sally Penfold says:

    Interesting, he just let you explain your ideas, not interrupting you with new ones (Howard Stern could take notes). And customer service is so essential. You talk so fast! Unfortunately I kept missing words.

    • shankman says:

      Email me if there’s anything you missed that you’d like me to repeat. Happy to do it. 🙂

  • Sally Penfold says:

    Interesting, he just let you explain your ideas, not interrupting you with new ones (Howard Stern could take notes). And customer service is so essential. You talk so fast! Unfortunately I kept missing words.

    • shankman says:

      Email me if there’s anything you missed that you’d like me to repeat. Happy to do it. 🙂

  • Sally Penfold says:

    Interesting, he just let you explain your ideas, not interrupting you with new ones (Howard Stern could take notes). And customer service is so essential. You talk so fast! Unfortunately I kept missing words.

    • shankman says:

      Email me if there’s anything you missed that you’d like me to repeat. Happy to do it. 🙂

  • Sally Penfold says:

    Interesting, he just let you explain your ideas, not interrupting you with new ones (Howard Stern could take notes). And customer service is so essential. You talk so fast! Unfortunately I kept missing words.

    • shankman says:

      Email me if there’s anything you missed that you’d like me to repeat. Happy to do it. 🙂

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