Series: Podcasting, pt3

Philip Morgan

(Readin' time: 8m 15s)

Since I talked so much yesterday about structural interest, let's move onto the next related concept, which is: being a good interviewer.

To be clear, you may not need to do this for your podcast. It might be a solo show, or a 2-people talking show, or something else. But a lot of business podcasts involve interviewing, and if I can die knowing I've contributed to fewer crappy business podcast interviews, I'll die a happy man. Furthermore, the core skills of being a good interviewer have beneficial spillover effects for the rest of your business (can make you a better diagnostician, for one).

Two kinds

"There are two kinds of people in the world. Those who believe there are two kinds of people, and those that don't." --Source unknown

As I was grinding the coffee beans this morning, I was reflecting on all the interviews I've done and wondering if it's really possible to organize them into binary pairs, or along a spectrum between two poles.

It kind of is possible to do this! In the context of a podcast, the two candidate spectrums are:

  1. Famous - Not famous guest
  2. You're prepared - You're not prepared for the interview

In fact, we could probably turn these two spectra into a 2x2 matrix. Lets do that:

  • A: Don't do this kind of interview. It makes you look like a jackass. Either prepare properly (moving you from A to B) or avoid doing do the interview.
  • B: These are great, but I have some aesthetic advice for this situation below.
  • C: There's a particular way you approach this kind of interview. You're less able to lead the interview, so you compensate by approaching the questioning differently. More on this below.
  • D: These are also great. I also have aesthetic advice for this situation below.

So quick summary: avoid situation A. The world has enough jackasses without you temporarily appearing to be a jackass during a podcast interview! Modify your approach based on whether you find yourself in situations B, C, or D.

Guest is famous, you are prepared (B)

My main aesthetic advice here is: look for the gaps. Aspire to be the interviewer that asks questions your guest hasn't already answered dozens or hundreds of times. Try to add something new rather than cover ground that's already been covered before by other interviewers.

In my case, this means I have avoided interviewing people I have wanted to interview because I can't think of something new or original to ask them about. Or in other cases, it means I've waited years--I really mean that; YEARS!--for the "stars to align" in a way that makes it possible for me to ask for an interview that adds something new rather than duplicates what's already been done.

Here's the problem my advice creates. Many famous guests you might interview are famous because they've published a book or given lots of talks. The very source of their fame (the book(s), talk(s), or the larger body of work those things are part of) is how most interviewers are going to prepare to interview them. That means the interviewers are "fishing from the same stocked pond", and this will cause their interviews to have a sort of sameness to them. They'll ask really similar questions because they're pulling those questions from the same source as other interviewers.

So the problem my advice creates is: your lowest hanging fruit for prepping for an interview with a famous person is the worst way to prep for that interview, because it will lead you to an interview that doesn't stand out from others.

This is compounded by the fact that most famous people (in the business world) are most receptive to an interview ask right before and right after they have published a new book. So what you tend to get is this highly concentrated (both in terms of timeline and content) dump of interviews appearing immediately before and after publication of their book where all the interviews are kind of the same. So just at the moment where it's easiest to ask this person for an interview you have the most structural difficulty in producing an interview that's differentiated and worth listening to!

My advice again is: don't do the interview just because access to the famous person is easier than usual.

In fact, asking for an interview with said famous person but focusing on a gap topic (one that's not really related to the book they've just published, but is something they find interesting) can be a refreshing change for them. Trust me, they get tired of answering the same questions over and over again too! They do it anyway out of a sense of obligation to their mission or audience, but they do find the experiencing wearying.

We can turn this into a rule of thumb. After a famous person publishes a new book, they'll spend roughly the next year promoting it by doing lots of interviews about the book. Wait about 6 to 8 months after their book comes out and then ask them for the interview. That's the point at which they'll be starting to tire of answering the same questions all the time and your ask to focus on a gap topic will feel especially refreshing to them.

Don't let your desire to focus on a gap topic move you from B (prepared) to A (unprepared)! You still gotta prepare, otherwise you still look like a jackass.

Guest is not famous, you are not prepared (C)

This category does not make you look like a jackass because there's an implicit understanding that if the guest is not famous, it's not possible to prepare in the same way you would with a famous guest.

That said, you will approach your questioning differently. With a famous guest that you've prepared well for, you'll have a sense of what questions might lead to interesting or surprising or insightful answers. (If you don't, you haven't prepared well enough!)

But with a not-famous guest, you won't know what questions will yield these kind of answers, so I suggest you adopt what I'll call an "A-B interviewing style".

Mode A is helping your guest tell a story. Mode B is when they happen to say something you think your audience will find interesting, so you halt the storytelling and dig deeper for a lesson or takeaway or explore a problem/solution they kind of glossed over in the storytelling. When you've mined this moment for all it's worth, you switch back to Mode A and continue.

Bob Lefsetz is excellent at this, although he's interviewing niche-famous people and Bob's industry knowledge and background makes him extremely well prepared for these interviews. So he's not quite operating within category C, but I want to link you to an interview with him anyway so you can get a sense of this A-B interviewing style:

Howard Stern also provides many examples of this A-B interviewing style. Here's me analyzing one for you:

Let's briefly sketch out what this A-B pattern tends to look like:

Interviewer: "Tell me the story of ?"

Interviewee: <Walks through a linear progression of events, mentions something interesting...>

Interviewer: "Can I stop you there? You mentioned $THING, and I'm curious if you can tell me why you did that?"

You repeat this storytelling-digging 2-step dance until you reach a conclusion.

I've linked to it before, but it's worth re-linking to this short video piece with Ira Glass talking about this A-B storytelling format:

Guest is not famous, you are prepared (D)

We find ourselves in quadrant D most often when we're considering interviewing someone who is a friend or colleague, and we've learned about their background through a process of osmosis.

There's not much to say here, except for this: try to approach the interview as both friend/colleage and proxy for your audience. Your audience won't have all the context you do, so you may need to ask questions you already know the answer to in order to build that context for your listeners. Also, your audience may find interesting and unfamiliar things that you find not interesting and familiar, merely because you've known your interview subject for a while. Try to avoid having that dampen your enthusiasm for the interview.

Finally, I should contextualize what I mean when I say prepared/not prepared. Professional interviewers like Terri Gross, Howard Stern, Andrew Warner and so on are always prepared. They have people who help them prepare.

The most prepared amateur interviewer I've ever heard is Tyler Cowen. Listen to any episode of his podcast Conversations With Tyler to see what I mean. If the guest has written a book, Tyler has read it. If they have written 10 books, he's read all 10. If their family members have written a book, he's read that too! The dude is a machine.

You don't have to prepare that much, but if you're interviewing a guest with a book(s), read their damn book(s). If they've done other interviews, check out a sampling of recent ones and their back catalog. If they've done talks that are published somewhere, same advice. Check their LinkedIn profile and learn about their career. Google them.

Repeat to this mantra to yourself: "If a potential guest's body of work is not interesting enough for me to become informed about it, I will not interview them on my podcast, no matter how helpful their fame might be for my podcast."

General interview advice

Let's close with a "lightning round" of some general interview/questioning advice. A lot of this I've said before elsewhere, but I want to summarize it here for sake of completeness.

  • Open-ended questions should comprise the bulk of your questions. These questions generally start with the words who, what, when, where, why, and how.
  • "Why" questions can be perceived as a challenge, so use these questions more carefully than the other open-ended questions.
  • That said, "why" questions can really deliver amazing insights when used as followup questions. Ex: Your guest tells you how they did something. You ask "Why did you do things that way and not another way?" This kind of "why" question can really deliver great stuff, so do remember to ask followup questions! Maybe don't ask "why" five times in a row, but do deploy the "why" question when you think it'll possibly lead someplace interesting.
  • When you're trying to set up a guest to tell you a story, the following can help:
    • "Take us back to $TIMEFRAME. What was happening then?"
    • "When did you start down this path?"
    • "Wait, can you go back and talk about the details of what happened between $EVENT-1 and $EVENT-2?"
    • "To help our audience understand, can you give more detail on $UNCLEAR-AREA?"
    • "Who else was involved?"

A big part of the appeal and power of narrative audio is these moments of emotional resonance. Even in the context of a business podcast, it's good to accentuate these moments if they occur during an interview. So don't be afraid to ask things like "how did that feel?" or "were you afraid?" or the like. And if this kind of stuff arises naturally, rather than rushing through it, allowing a beat for your audience to soak in and reflect on this emotional moment can be really powerful.

Allllrighty! I think that's a pretty solid treatment of the interviewing topic. Tomorrow I'll move on to the question of publication: how often, how to make use of seasons or miniseries, and stuff like hosting, etc.

Until then,