🤔 Interviewing: How to ask killer questions on podcasts and panels

Ft. Sean Evans, Ashton Kutcher, Mila Kunis, Logic, John Boyega and Courtney Cox

Sean Evans has built a reputation of being one of the best interviewers on the planet. He’s so good that there are compilation videos dedicated to the quality of his questions and his guest’s reactions to them. His secret?

Ask non-obvious questions

Aim to elicit the response… ‘That’s a gooood question’

The standard of questions asked on 99% of podcasts, panels and fireside chats is painfully poor.

Such a wasted opportunity.

Having listened back to my attempt at podcasting, I too fall into this camp.

What I’ve learned from watching Sean is that something very special happens to your guest when you ask a killer question:

  1. First, their whole face lights up 😲, 

  2. Then, they compliment your question 😊, 

  3. Finally, they turn off autopilot so they can give it the thoughtful answer it deserves 🤩

Killer questions remove the status gap.

Sean’s guests, despite being significantly more famous, treat him as a peer. There’s mutual respect.

Land one killer question and the reciprocity you’ll get in return will pay dividends.

Not least, your guests will shout about their interviews to their equally impressive friends and their followers on social media - which is critical if you’re looking to grow your podcast.

In this 106-second clip, you will see 6 of my favourite Sean Evans questions, complete with reactions from Ashton Kutcher, Logic, Mila Cunis, John Mayer, John Boyega and Courtney Cox… 🍿

[For context, the premise of Sean’s show ‘Hot Ones’ is that interviews celebrities while they eat progressively spicier chicken wings 🌶️.]

Here are three types of questions that you can steal from Sean (and a bonus tip to take them to the next level):

  1. ‘Connect the dots’ questions 🔭

    These questions force you to go beyond the obvious because the require you to make connections between different experiences that your guest has had. 

As someone who’s done X and Y, I think you’re uniquely qualified to be asked the following question:

  1. ‘Best and Worst’ Questions ❤️‍🔥

    They’re so incredibly effective at getting your interviewee fully engaged. Giving them the chance to talk about things that they love ignites their passion. What’s more, we all love to talk about what frustrates us and it can be as cathartic for the audience as it is for your guest. 

‘What are the best and worst things about…’

  1. ‘Recommendation’ Questions 🧜
    Audiences love receiving recommendations as much as guests love giving them. The most obvious recommendation question to ask is about books, why not make them about people? So allow your guests to shine a spotlight on someone they really admire.

Who do you think is getting overlooked, or has the potential to be the rising star in your field…

  1. Bonus: The Question Pre-Amble 🎙️
    Giving your question some context before asking it isn’t just an opportunity to ground your guest and listeners, it’s also an opportunity to show that you’ve put time and effort into your research. Aim not to ask them about anything you see on their bio. The more specific you can be with your context the better.

    For non-obvious question inspiration, rather than head to their LinkedIn Bios or website:

    1. Define the three most important things that going on in their industry/field 🌍

    2. Search for things others have said about them 🗣️

    3. Deep dive into their old social media posts 📜

    4. Listen out for questions other podcast hosts missed 🤐

    5. Analyse the content they interact with on their social channels 👍

And to those of you still reading this who are usually the guests, not the hosts, here’s a little tip for you…

Condition your interviewer 💪
Send them this article - or in your acceptance message write something like this:

Thank you so much for asking me to be on your podcast. I would love to.

I should note that these days, I’m being much pickier about whether or not I share an interview on my social channels. So don’t be afraid to challenge me with your questions, they’re much more fun and that’s what usually gets the best answers out of me.

Just think…

If you put some of these into practice, you could very quickly build a reputation as the best interviewer in your field. I wonder, what opportunities might that create for you?


p.s. We have 9 spots left for our May intake at MicDrop, our public speaking community for tomorrow’s thought leaders.

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