How to Ask a Better Question
January 24, 2025 · 5 min read
The best interviews aren't scripted. They're prepared. Here's the framework I use to walk into every conversation.
Every bad interview I've ever seen has the same problem: the host is reading questions. Every great one has the same secret: the host is listening for them.
The difference isn't talent. It's preparation. And preparation is not the same as a list of questions.
The three columns
Before every interview, I write three columns on a page.
The first is facts — the things I need to know before we sit down. Dates, credits, who they've worked with, what they've said publicly. This is the homework. Skipping it is disrespectful.
The second is themes — the ideas I want the conversation to touch. Not questions. Themes. "Loyalty." "The version of yourself the industry sold." "What losing that friend actually cost you." Themes are directions. Questions are exits.
The third is traps — the moments where I know I'll be tempted to insert myself instead of listening. My own opinion about a beef. My own take on a record. My own story that's kind of like theirs. Every one of those is a trap. The column exists so I recognize them in real time.
The follow-up is the interview
Anybody can ask the first question. It's on the internet. It's the second question — the one that grows out of what they actually said, not what you planned to ask next — that separates a conversation from a press junket.
The rule: never let the answer to your last question die without at least one honest follow-up. "What did that feel like?" "Why do you think it landed that way?" "Would you do it again?" These are not clever questions. They are respectful ones. And respect is what makes people open up.
Silence is a question too
When someone finishes an answer and you don't move for three seconds, they will almost always keep talking. And the part they say in that space is almost always the part they didn't plan to say.
Most hosts are terrified of silence. Learn to love it. It's where the interview actually happens.
The last question
I ask a version of the same last question to every guest: "What's the thing you wish somebody had asked you today that nobody did?"
Half the time, they laugh. The other half, they answer it. And that answer — that answer — is almost always the part of the episode that ends up on the poster.