Click here to read part 1 first (otherwise, how the hell will you know what we’re talking about in Part 2?).

4. Your New Conversational Superpower: “Do You Mind Me Asking…”

When my buddy Matt asked me about interview techniques, this was exactly the kind of “conversation hack” he was looking for.

Here’s how it works:

Your author is telling you about that time they got fired from their own company in 2013.

They say, in passing, “That was actually the year my husband and I got divorced. The first few years after that were interesting. Anyway, in 2015 I started my next company…”

Hold your horses right there, cowboy.

You heard them briefly allude to something deeply serious (a divorce), without stopping to linger on it. Will the details of their split make it into their book? Maybe. You can’t know for sure yet. But you’d be doing them a disservice by not finding out more.

Pause them and say, “Before we get into your next company, which I definitely want to hear about, do you mind me asking about the exact circumstances of your separation with your husband?”

See what you did there?

In a low-pressure, indirect way, you’ve asked them for more detail without actually asking for more detail. You’re only asking hypothetically.

99 times out of 100, they’ll dig as deep into the subject as you need for the book (and maybe a little more).

Sure, they might have talked about the painful event regardless of how you asked the question, but this technique is more for you than for them:

It’s difficult asking people about deeply personal aspects of their lives. When you soften the blow with this technique, you make it easier for both of you to broach a sensitive subject.

I don’t care if it’s a professional interview, a conversation with a friend, or a date—I use this phrase so much I barely notice it anymore, and it works practically every time.

When to Use This Technique:

If your author mentions something in passing that may be painful or embarrassing, but is (potentially) integral to the book.

Note:

If they say, “No, I’m not ready to talk about it,” then obviously respect their wish. That’s rare, but it happens. At the very least you will have sparked the subject in their mind, and they will likely bring it up of their own volition later on.

5. How to Get Out of the Weeds

You’ve just spent the last hour talking about your author’s departure from their first company, and their subsequent divorce. It was all fascinating and necessary information for their book.

But now all the sudden they’re telling you a story about their first year of junior high.

Are they presenting the skeleton of a thrilling origin story you can detail in their book? Or are you both so deep in the weeds that you can’t see the trail anymore?

You’re not sure, so you let them continue. As the story wraps up, you ask a few clarifying questions, they answer, and you’re now quite certain that this story will serve no purpose in the book.

Early in my career, I would have assumed this tangent was somehow a failure. Like I’d let us waste precious interview time, and it was my job to completely switch conversational gears to get on track.

To make matters worse, I would switch gears without asking for the author’s input, assuming that I knew better than them that this story wouldn’t make it into the book.

I was inexperienced, wrong, and just plain hard on myself. Eventually, I learned to be kinder to myself and I learned to involve the author more in my thoughts as we spoke.

Even if you’re certain the story you just heard will have no place in the book, give your author a chance to weigh in. This is a collaboration after all.

Say, “That’s an interesting story, author, but let me ask a silly question: What makes that story necessary for the reader to know?”

This question works in two ways:

1. It you’re wrong, it allows the author to provide the missing context that would actually make the story necessary for the book.

2. If you’re right, and the story wasn’t necessary, this question is a good way to gently switch gears and move into something more salient for the reader. (They’ll say something like, “Hm, I’m not sure it is.” To which you can respond, “No problem. That provided some interesting context for me that may prove necessary later on. For now, let’s switch gears and move into…”)

Bonus: this question helps coach your author into thinking about their stories through the lens of what is necessary for the reader to know.

When to Use This Technique:

When your author is getting lost in the weeds, and you’re nearly certain what they’re saying won’t make it into the book.

6. Give Them a Breather

Talking for an hour-plus on end is pretty damn hard.

But if you’re like me, you have a flawed script running through your mind during interviews. You know what I’m talking about—the script that pops up every time you want to interject with your own experience, or your own anecdote:

“Just keep that thought to yourself. This is about them, not me.”

It took me a long time before I noticed I was even doing this, and even longer to make the necessary realization:

You’re not being self-centered by sharing about yourself in an interview. In fact, when done at the right time, you’re actually doing your author a favor by interjecting: they get to breathe for a minute while the spotlight is on someone else.

This one is tough to get right. Really tough. Even the best get this wrong sometimes.

Perfect example:

I had the privilege of producing a video podcast with a very prominent author. I won’t say his name, but I’ll tell you this: he’s such a good interviewer that his interview-centric podcast has been #1 in the world multiple times throughout the last decade.

Anyway, he was about an hour into the interview and it was going great. He asked amazing, well-researched questions, and the guest responded with interesting and vulnerable stories about himself.

But I noticed something: the host didn’t do much talking himself. Sure, he interjected here and there with a clarifying question, a joke, or a bit of context for the listener, but at no point did he grab the spotlight of the conversation and shine it back to himself.

Up until that moment, I thought that was the right way to do it. What happened next showed me I was wrong.

About 90 minutes into the interview, we all took a break. After the host left the room, his guest leaned back from his microphone and slumped into his chair like he’d just finished a 10-mile run. He looked over to me and stuck out his tongue in an exaggerated pant, as if to say he was dog tired from talking.

I was just about to ask him something when he cut me off, saying, “What do you think of Austin?”

With the host out of the picture, it seemed the guest just wanted to hear someone else talk for a minute. The poor man needed a breather (of course I obliged and rambled about tacos and barbecue for as long as possible).

That podcast host is world-class, but this poor guy just needed a break from talking—and he hadn’t gotten it yet.

Yes, you have an agenda for your interview—to get a book out of your author—but you won’t make good on that agenda unless you’re having a conversation, which means you have to spend some time talking too.

Don’t worry: you only have to turn the spotlight on yourself very briefly. Most authors will naturally bring the conversation back to the subject at hand when they’re ready. Otherwise, just say, “Sorry about that, author, I got us off track. We were talking about…”

For the most part, only the most polished speakers—people who talk in front of large crowds on a consistent basis—are comfortable plowing forward without many breaks.

For everyone else, do them a favor and interrupt every once in a while with something about you, or something you notice as it relates to their book.

They’ll thank you for it, and you two will get even closer as they learn more about you.

When to Use This Technique:

When you can audibly hear your interviewee sighing, or if they stop to take a sip of water. Use that pause as a chance to step in and talk for a moment.

7. What to Do When You’re Lost

We were 6 hours into interviews and I realized something that made my stomach drop:

We were fucked.

Something struck me in the middle of interviews that made it obvious the outline we’d put together was not going to serve us anymore, and we had to completely change the angle we took for the second half of the book (and maybe the entire thing).

Now, there’s a reason why I don’t create static outlines—the kind you lock in before interviews: because the best books are structured based on content, not the other way around. So I keep the “outline” fluid all the way through.

But this was different…

I had to blow up the whole goddamn thing without freaking out my author.

I went into the next call feeling lost, not knowing exactly where to go except for one possible path:

The author had mentioned a story he didn’t have a chance to tell in the previous call. That was good enough for me.

We started with that story, which brought up an interesting point we hadn’t considered before, which led to another example, and so forth. Before we knew it, we had even better momentum and content than we’d had in the first half of interviews.

All because I followed one rule, which saved that project:

Follow whatever is interesting.

In psychotherapy (which I am a huge proponent of, and which has made me a better interviewer), there is a general rule that therapists follow:

If the analysand (patient) is talking about something and you feel bored as the therapist, that’s for a reason—whatever the patient is talking about is likely not salient.

If what they’re saying is interesting, it’s likely important at that point in their therapy.

I used this mindset as the guiding light for interviews with that author after we scrapped the outline.

I don’t know exactly where this is going, but I’m interested, so let’s keep digging.

If you do nothing else other than follow what is interesting, you’ll find yourself in some pretty fascinating places you never would have expected. More importantly, you will get a better book than if you’d followed a strict outline.

By the way: that author whose outline we imploded? Yeah, his book turned out so well that he left the testimonial on my homepage.

When to Use This Technique:

When you’re, well, lost.

8. Antagonize Consciously (and Sparingly)

Certain people thrive on combative conversations and being underestimated. An even smaller minority of people can only get fired up this way.

You’ll likely know these people when you meet them.

They’re the opinionated and (outwardly) confident people who aren’t afraid of confrontation. They’re energetic, charismatic, and type-A.

If you’re in an interview with this person and you notice their energy is lower than normal, or that they’re talking in hard-to-grasp abstractions, first call attention to it.

“Hey, author, is everything okay? You seem a bit down today.”

If they’re going through some shit in their lives—like their dog is dying or their company lost a big client—you guys should be close enough that they tell you about it straight up when you ask.

In that case, ask if they’d like to reschedule the call so they can take care of the more important things on their mind.

However, if they say they’re just feeling a little off, or you get the impression that they’re coasting, you may have to kick them in the ass a bit.

Devil’s Advocate

Here’s what I mean:

I was talking in person with a CEO I used to ghostwrite thought leadership articles for. He was sleepy and slouched in his chair as we spoke, completely disparate from his normal energetic demeanor.

He spoke in circles about how sacrifice is necessary for business success. I wasn’t getting enough material for a great article, so I had to bait him.

I said, “Wait a minute. Don’t most CEOs have money, freedom, and time without having to sacrifice anything?”

He popped up so fast I thought his chair had electrocuted him to attention. All the sudden he was giving me gold. I knew him well enough to realize that my question was completely opposed to his beliefs, so hearing it was sure to get him a tad pissed off.

And it saved the interview.

In general, all you have to do is play devil’s advocate for antagonism to work properly. You can even soften the blow by explicitly saying that’s what you’re doing.

Say your author is a dentist:

“Just to play devil’s advocate: Why should I floss? I read recently that flossing is actually bad for your teeth.”

Say that to a dentist and you’ll get them hotter than a two dollar pistol—and trust me, their response will be passionate and full of useful content for the book.

Only certain people respond well to this antagonism, and even with those unique few who do, you’ll need a solid rapport with them before you can pull this off.

Warning:

Antagonizing with the wrong person or at the wrong time can totally kill your relationship. Use this technique wisely.

Used sparingly, conscious (and gentle) antagonism is one of the best ways to turn a lackluster interview into a great one.

When to Use This Technique:

When an otherwise energetic and confident person is coasting, getting lazy, or having an off day.

9. Practice Beginner’s Mind

Simply put, beginner’s mind means approaching subjects—even ones you’re intimately familiar with—with a spirit of humility, openness, and lack of assumptions.

This attitude is just as necessary in interviews as genuine curiosity.

No matter what subject matter your author is an expert in or what type of story you’re writing with them, assume that you are a neophyte—a beginner—learning it for the first time.

When looking for a ghostwriter, most authors look for someone with background knowledge. It seems logical: a ghostwriter with knowledge on the topic will be an advantage, right?

An author is writing a memoir about their childhood in foster care, so they want to work with a ghostwriter who also grew up in a foster home.

They’re writing a book about baseball, so they want to work with a baseball fan.

My take?

Shared experience between an author and ghostwriter can be an advantage, but more often it’s a handicap.

Why? Because you know too much about the subject, so you don’t make your author explain themselves enough.

You know what a foster home is like, so you don’t ask them to explain it in as much detail.

You know what a curveball is, so you don’t make them explain the difference between that pitch and a slider.

In short, when you know too much about your author’s subject, you’re just not dumb enough in the interview.

Your expertise inhibits your ability to get great interview content.

There’s also a certain measure of insecurity that keeps you from using a beginner’s mind. Understandably so! You don’t want your author to think you’re actually stupid.

You don’t want them to say, “Why are you asking me what a slider is? I thought you were a baseball guy—that’s why I’m working with you.”

Fair point. That’s why you set the expectation from the outset—

“Listen, author, I know a big reason why we’re working together is because we share X experience. Even with that shared experience, I’ll still ask you very basic and sometimes obvious questions. That’s because I want to get all of your stories and details of your knowledge in your words. That way I understand the nuance of your experience. So if I ask you “What’s the difference between a curveball and a slider?” I’m asking on behalf of your reader. Cool?”

If you don’t set that expectation, and you don’t ask the so-called stupid questions you already know the answers to, you’ll end interviews with a horrible realization:

Your transcripts aren’t good enough. You’ll have to fill in a ton of blanks in the writing process.

Without operating from a beginner’s mind, you’ll feel like a genius during interviews. But once you get into writing and revisions, you’ll realize you made more work than necessary for you and your author.

Do yourselves both a favor and ask the dumb questions.

When to Use This Technique:

All the time, and especially if you’re an expert on the subject your author is writing about.

The Fallacy of Interview “Techniques”

I’ll be frank: I kinda lied to my writer buddy Matt when he asked me about interviewing advice. I basically told him that interviewing techniques were a fallacy, and he should focus on genuine curiosity (and beginner’s mind) instead of hacks.

But it turns out I was wrong! There are a few hacks after all.

I can still tell he’s anxious in conversations (especially with his authors) and if he asks me what I ate for breakfast one more time I’m gonna choke him with a jelly-filled donut.

But I’ve also seen him open up with people more than he ever has, and in the process he’s been writing better books, and he’s noticeably less anxious in conversations—interviews and non-interviews alike.

To sum up:

1. Find Out What They had for Breakfast

2. Show Them That You’re Teammates—Even If You’re Rivals

3. The “Put Me in That Moment” Technique

4. Your New Conversational Superpower: “Do You Mind Me Asking…”

5. How to Get Out of the Weeds (by asking “Why is this necessary?”)

6. Give Them a Breather

7. What to Do When You’re Lost (take a cue from psychotherapists and follow what is interesting)

8. Antagonize Consciously (and Sparingly)

9. Practice Beginner’s Mind

Thank you for reading! If you’re interested in more, sign up for my mailing list in the box at the bottom.