Podcast interviews with thought leaders or experts break down quickly when you ask questions outside your guest’s wheelhouse: I call them digressive questions. They introduce awkwardness for your audience, the host(s) and they’re unfair to your guest. This could prevent the guest from sharing your show.
On a podcast project I was hosting, a client asked me to prioritize a few questions in an interview with an expert in a particular field. “I don’t think the know anything about this subject,” I replied. “You can always ask and see what they say,” the client replied.
No. You can’t. I told him what I’ll tell you: Podcasts aren’t normal conversations. Bad questions make bad shows.
In a every-day conversation you can meander aimlessly and jump topic to topic. It should be obvious to you however, this is rarely interesting to third parties, or, your audience. Podcasts should feel like a warm conversation, but they’re a performative discussion with an objective to educate and entertain them.
In my first live radio experience for iHeart, my new co-host and I realized we couldn’t just show up with topics and chat. Sometimes, I’d introduce a topic minutes from a break, not knowing my co-host wanted to comment on it. Other times, she’d introduce a topic I had a planned segment for, ruining the segment. It sounded chaotic. We fixed the problem by loosely planning the show by giving each other our topic list ahead of time.
Structured podcast conversations sound more natural and authentic. But how do you “plan” with a guest?
Great interviewers avoid bad questions
Great interviewers ask great questions, but they’re also good at not asking bad questions—it’s a hidden trick most listeners rarely catch.
Consider the impact of a host asking a question, and the guest promptly replies, “I have no idea. That’s outside my wheelhouse.”
An expert guest could feel embarrassed at best, or at worst feel pressured to attempt a bad answer.
This also puts the host in a poor position. Do they apologize? Pivot to another question?
A rich podcast discussion avoids asking digressive or stupid questions entirely. This is achieved when the host spends time on proper research and planning in advance.
How to ask good podcast interview questions
In my 10+ years of interviewing iconic people and top-of-their-field experts on podcasts and radio, great interview questions come from meticulous research. Only when you fully synthesize a person’s body of work, can you effortlessly interview them.
In most cases, I know the general structure of an answer before I even ask the question. Yes, sometimes the content of an answer is surprising, but the general direction isn’t. Almost like a lawyer, I rarely ask questions I’m unsure how they will answer. The nature of a host’s research depends on the guest of course, so here are a few starting points.
Podcast Guest Research Ideas
TV Interviews
For politicians like Tulsi Gabbard and Andrew Yang, I watched 15+ hours of interview and debate responses to understand what questions they got often, that I should avoid, and which questions they seemed to shy away from. I took thorough notes.
Books
For authors like Daniel Pink and Cal Newport, I read their entire book and last few months of articles they had published, or their own blog. I’ll often request uncorrected proofs via PDF to read and highlight (depending on your podcast reach and credibility, you may have to buy a paper copy.) I’ll take notes with page numbers as “bullets” to keep thoughts organized.
Articles
For experts or consultants, I read the last 6 months to 1 year of articles they have written. Often you can find them linked from their personal website, but this may require a google search. I print every article to PDF and send to my ReMarkable where I highlight and take notes.
Podcast Interviews
It seems like almost everyone is going on podcast interviews. For some guests, I’ll go listen to their last 10 or more podcast interviews. Even though most interviewers are poor and don’t ask good questions, many times you can hear clues or nuggets in their answers that are useful to explore later.
What if there’s no research available?
Experts are people who have a body of work or established credibility in a space. If they don’t have a body of work, they’re not an expert and your interview style takes a new direction. For example, if you have a local city council person they may not have a book or research papers to their name. In these cases, your research attention shifts to a topic, not the guest.
If you’re interviewing a city Mayor about a new proposed law, you’d research laws and local regulations. While it’s vital to research the guest, it’s more important to know the issue and topic at hand. If the guest doesn’t have an answer in this case, it doesn’t reflect poorly on you—it holds your guest accountable.
Bottom Line:
The bottom line: what you don’t ask is just as important as what you do ask. You should know your guest in vivid detail, and have a sense of their answers long before the record light flicks on.
