“So, Do You Always Wear
White Underwear?” –
How to Write an Exciting Interview

Interviewer: “Where did you grow up?”

Famous person: “Florida.”

Interviewer: “Where did you attend college?”

Famous person: “Florida State.”

Interviewer: “What was your major?”

Famous person: “Soil and water science.”

Y-a-w-n. That’s what your reader will do when you write an interview like most run-of-the-mill writers.

After all, common sense tells us the interview process should be logical and matter-of-fact. But to write an exciting interview, you have to throw common sense out the window.

As copywriters, there are two major reasons why we should know how to conduct and write a great interview:

  • An interview with a potential client and/or the creator of a product you’re writing about can unearth great information you can use to make your promotion a winner. Usually this is information you can’t get any other way, and often it can be the source of your “big idea.”
  • You can make money by interviewing experts and selling those interviews to the appropriate publications. (Keep an eye out for an upcoming article in “The Golden Thread” about how to do this.)

To find out exactly what makes a good interview, I spent an hour with Michael Masterson at his neighborhood cigar bar. This is what I learned …

To make an interview exciting, you need to do a little risk-taking with each of the four elements that make up a great interview:

  1. Picture

    An average interview usually shows just a headshot of the person being interviewed – a face with little or no expression. But this is boring and safe. Instead, tell the person you’re interviewing to send in a full body photograph. Or, to make it even more interesting, tell him to have a goofy expression on his face (like sticking his tongue out). Or have him strike a funny pose. If it’s a more serious publication, have him take a picture with his family, playing in the backyard … or doing something active, like skiing, or bike riding.

    Bottom line is, stay away from the norm and have him do something unusual, interesting, or provocative.

  2. Questions

    Avoid typical interview questions. Instead, ask questions that are intriguing, or lead the interviewee to reveal an interesting bit of information. For example, instead of asking, “How did you achieve your copywriting success?” ask, “They call you the ‘Godfather of copywriting’ … what three qualities do you think you share with Marlon Brando?”

    Michael showed me an interview in a cigar magazine that does this brilliantly. The picture shows a full body shot of an older man in a white suit and straw hat, smoking a cigar. The first question the interviewer asks is, “So how many white suits do you own?” followed by questions like, “Have you considered pin stripes?” and “So, do you always wear white underwear?”

  3. Answers

    You will be more successful as a copywriter and interviewer, if you take the initiative to ensure you get good, interesting answers from the person you’re interviewing. As mentioned earlier, boring questions lead to lackluster answers.

    But if you’re asking interesting questions and still getting mundane answers, keep prodding. Keep asking the same question a different number of ways until you get an interesting bit of information. For example, say you’re interviewing a natural-health specialist:

    You: “Besides educating others about natural health, what are you passionate about?”

    Interviewee: “Hmm … I don’t know. Wine, family, and jogging I guess.”

    (Pretty boring … let’s try this again … )

    You: “If you had all the money and time in the world, what would you be doing right now?”

    Interviewee: “Riding in a Porsche 911 Turbo in Napa Valley, listening to music while on my way to a wine tasting.”

    (Now we’re starting to get somewhere … )

    You: “If you could have two super powers, what would they be and why?”

    Interviewee: “I’d love to have super strength like The Hulk, because as a kid I always wanted to be the world’s strongest man. I’d also have incredible speed, like The Flash, because I love the adrenaline rush I get from racing.”

    (Voila! You’ve gotten the interesting information you need.)

  4. Structure

    This is the order in which you publish the picture, questions, and answers. Most writers feel the need to do this in a logical sequence. But again, that makes for a boring interview. To have the strongest interview possible, you need to start and end strong. Pick the most provocative questions and answers to be featured at the beginning and at the end. From there, let your emotions guide you. Do you feel it would be more appealing to let the reader know your famous person wears white underwear in the middle of the interview? Maybe you want to leave it as the closing question.

    You’re in complete control at this point. Just avoid making it too linear and logical. And remember, you can’t change what a person said. You’re simply “editing” and sifting through all the mundane stuff to find the gems.

Now that you know what it takes to write an exciting interview, check out the rest of the conversation I had with Michael at the cigar bar …


Get Down ’n’ Dirty With Michael Masterson

Michael Masterson (standing) demonstrates
“old school” method of learning copywriting

Guillermo: I hear you’ll be headlining at this year’s Bootcamp. Any chance you’ll be auctioning off a cardboard cut-out of yourself, like you did last year?

MM: I don’t know what Katie has in store … you never know. I was hoping I’d be auctioning off kisses to very select members of the audience. Last year, if I remember correctly, a very hairy guy won the cardboard cut-out of me. Maybe I should reconsider.

Guillermo: If you could be a copywriting superhero, what one power would you have?

MM: X-ray vision … to look into the heart and mind of my prospect.

Guillermo: How do you think copywriting got its name?

MM: Next question …

Guillermo: You’ve mentioned before how your Brazilian Jiu-Jitsu training parallels the process of learning copywriting. Any insights you can tell our readers?

MM: Time for a serious answer. There are basically two forces in life: relaxation and contraction. Or, to put it in psychoanalytic terms: ego and the relaxation of the ego.

Being successful at Jiu-Jitsu requires a healthy ego. You use it to push yourself to become better. But mastering the specific skills requires relaxing the ego. You have to be willing to be beaten – over and over again – before you can be really good.

The same is true for copywriting. The ego compels you to persist. But you have to be willing to be bad – and learn from being bad – before you can be really good.

Guys who try to muscle their way to victory in Jiu-Jitsu fail because they lack technique. And if they persist in using muscle, they never get much better. If a copywriter decides he’s good before he truly is good, then it will be difficult for him to accept criticism and learn from his shortcomings.

Learning when you’re not relaxed is a very slow and painful process.

Guillermo: I guess this painful method is what you’ve termed the “old school” method of learning copywriting?

MM: Yes, the “old school” way of learning how to write – known as the critical method – was both slow and painful. In the old days, a young copywriter would have his copy ripped to shreds by some authority. If the copywriter had a bit too much ego, it made him very defensive. It led to arguments and resentment and lots of wasted time.

Guillermo: So, what’s the new way of learning, and how is it like Brazilian Jiu-Jitsu?

MM: The “new school” process of learning copywriting is like learning Jiu-Jitsu … where you and your teacher are very relaxed. You go through the motions painlessly. You’re not worried about getting beaten up, so you can pay attention and learn specific skills quickly.

Jiu-Jitsu is the gentle art of fighting. The “new school” method is a gentle way of learning copywriting.

Guillermo: So, no more “old school” copy critiques?

MM: Hey, if I have to, I can still verbally crush or choke a novice copywriter into submission like the old days. But I’m a kinder teacher now.

Guillermo: I guess you could also say there’s a lot of “setting up” in Brazilian Jiu-Jitsu. You have to set up your opponent to get the submission … and in copy, you have to set up your prospect for the sale.

MM: Yeah, but now you’re jumping to a different analogy. Let’s not spend the rest of the interview with this belabored metaphor.

Guillermo: I hear you’re going to have a book signing during Bootcamp. Any tips on …

MM: Signing books? Yes, use a very simple signature. Three indecipherable slashes are what I recommend.

Guillermo: Any plans to use the left hand in signing, when the right hand gets cramped?

MM: The thing about the left hand is … um … it’s … oh, never mind.

Guillermo: Can you tell me a little bit more about the “new school” method of learning copywriting?

MM: I developed the “new school” method by relying on the good thinking of three of the best copywriting teachers I know: Bill Bonner, John Forde and Michael Palmer. It is very powerful. And it is very fast. It used to take years to become a good copywriter. Now it can be done in months.

Guillermo: Why’s that?

MM: Part of the reason it takes copywriters so long to get good is because they don’t get a lot of feedback.

The “new school” method of learning solves this problem. Instead of getting their copy reviewed only six to eight times a year – as was customary in the “old school” way of doing things – the “new school” method allows copywriters to get their copy reviewed much more often … sometimes hundreds of times in a single year.

Guillermo: If during Bootcamp, somebody sees you in the hallway and wants to pick your brain for 30 minutes, what do you recommend they do?

MM: My preference would be to offer me $1 million, my minimum fee for consultation. That always warms the cockles of my heart. Second to that … a plunging neckline? Seriously, though, bowing and scraping are usually sufficient.

Guillermo: I’m sure you’ve heard how many sports athletes have lucky charms … like lucky socks or underwear. Do you have a lucky outfit you wear to help you write “A-level” copy and bring out the creative genius in you?

MM: Can’t say that I do. But as anybody that’s around the office knows, I tend to spend a lot of time writing in my wrestling clothes.

That’s one of the great things about writing for a living. You can do it on your own terms.

I like writing right here at Joe’s Cigar Bar. I can write and smoke at the same time. Often I find there are tears streaming down my face as I write. Of course it’s not the tear-jerking power of my prose, but the sting of 32 other cigars being smoked in the room.

Guillermo: What do you think about multi-tasking while you write?

MM: I don’t believe in multi-tasking at all. I believe it’s a complete crock.

Guillermo: Do you need to get into the zone to write well?

MM: No. Professional writers can’t afford to wait for the moment. Even when I’m feeling especially dumb, I write anyway. I start by writing anything, knowing that some amount of what I’m writing will be deleted later. Eventually the writing itself gets me in the zone.

But waiting for the zone is just an excuse for putting off work, as far as I’m concerned. When it’s time to start writing, you need to start writing. When this becomes habit, the time it will take you to get into the zone will become fairly short.

Guillermo: Where do you get your ideas?

MM: From my daily life – conversations, experiences, etc. And from reading. I start each day by reading at least one newspaper. I read quickly and pragmatically, always searching for one thing that seems clever or useful.

Guillermo: Well, Michael, I’m almost out of time, so I’d like to ask you one final question. When editing copy, it’s been said that cutting out portions of what you’ve written is like disinheriting your own children. Would you say that’s pretty accurate for you, even as a Master Copywriter?

MM: When people suggest I delete something I’ve written, I do have a little bit of an instinct to save it.

Maybe the better metaphor for deleting your copy is getting rid of bad friends. In a self-destructive way it feels kind of good to have them around … but once you finally get rid of them, you know you’re so much better off.

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Click to Rate:
Average: 3.7
Published: October 10, 2008

9 Responses to “How to Write an Exciting Interview”

  1. I love this article, very helpful insights. I have so many ideas running through my head. Interviewa have all been a passion for me to write. I subscribe to time magazine and I first read the short interview of that month. I have my first interviewee in mind. The person of interest is an second generation italion butcher on Elizabeth St in Soho new York. Martin scorsaci film one of his first movies in his place of business. I'll tell you how I did and maybe I'll sent it to you so I can get a fair critique

    Guest (al colon)March 26, 2011 at 8:51 pm

  2. this helps alot cause in my school were doing this that's why

    Guest (aruthi)September 22, 2012 at 2:14 pm

  3. it's really helpful while writing an interview, there is no alternative to interesting questions!

    Guest (zakia sultana)December 9, 2012 at 1:56 am

  4. This is sweet! Perfect for my dose of inspiration before I write for our school newspaper. Thank you!

    Guest (Abegail)April 22, 2015 at 9:18 pm

  5. this is helpful thank you

    Guest (arminias surong)October 27, 2015 at 2:04 am

  6. Its really good in my class

    Guest (Selvaraj C Jamnalli)November 3, 2015 at 6:03 am

  7. THis was not very efficient!

    Guest (renaigh)September 7, 2016 at 3:04 am

  8. I'm doing this for a school paper this did not help at all:( :( :( :( :(

    Guest (shasha)January 24, 2017 at 2:10 pm

  9. Very helpful, thanks! I'll be writing interview plays in no time!

    Guest (Alliwackbushunalaop)November 6, 2017 at 1:24 pm


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