Why Generic Questions Kill the Interview

If you’re not getting the kind of cool stories, insight, or energy you expected from your guest, don’t automatically blame them.

Start with asking yourself this:
“Is it POSSIBLE they’ve got this question a thousand times before?”

You know the kind I’m talking about…

“What would you tell your 18 year old self?”

“What keeps you up at night?”

You didn’t invite them on to showcase how lazy you are - right?

Behavior breeds Behavior

Can we be honest with each other?

Bad questions aren’t always bad—they’re just common. And the goal is to be different and memorable. Here’s some more cringey Qs:

• “Tell us your backstory.”

• “What’s one lesson you’ve learned from failure?”

Fine. But not memorable.

If your guest doesn’t have to take a split second to even consider their answer, then it’s their normal canned response and listeners will likely not care to listen on. Night night time Steph Curry style.

So What Makes a Better Question?

1. It’s something you’re actually curious about (but still valuable to the listener)
   
   Example: Asking former President Barack Obama if he’s so in love with basketball because he sucked at it.
   

2. Something that shows you did your homework.
   “I saw your post about ___” or “You mentioned in another interview…”
   That kind of thing immediately earns respect and changes the tone.
   

3. It’s connected to your audience.
   If your listeners are real estate agents, don’t ask your guest what they thought AMEX updating their loyalty points and how to travel hack.

   
   Ask what they did the day when their clients switched agents after they did all the freaking work.
   

4. It steers away from enabling guest to plug thier sh*t.
   A lot of guests come on ready to sell and act like they aren’t. You can honor that (at the END of the episode), but don’t let it dominate.
   
   Instead ask why that thing exists in the first place.
   
   Example: “We know you specialize in sales training courses, but tell me about how you conceptualized the very FIRST module? Was it easy? Scary?”
   
   Pull the Thread!

   When someone gives a decent answer (a little string) — pull on it to unravel more.
   
   Example: Guest says “I wanted to be able to make so much money that I could retire my parents.”
   
   You say -”What made you want to do that?”
   
   Guest: My parents were both immigrants and worked odd jobs all their lives to support my brother and I.”
   
   You ask “What kind of memories come up when you think about what they did?”

   It’s not about being dramatic—it’s about actually learning something worth listening to.

Content You Should Check Out 

Meet Arjun- my friend and client who is a mortgage guru and 2 time Taekwondo world champion. He got real deep discussing some pivotal childhood moments that shaped how he approaches opportunities .. and recognizes them.

I wouldn’t share it if you couldn’t learn from it.

If you don’t want to watch you can also listen here.