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Ask Great Interview Questions Like a Journalist

At the ripe age of 28, after years of performing odd jobs at a small radio station, Larry King found his first job interviewing people on the radio.

But he wasn’t sitting in front of that famous globe backdrop or interviewing world leaders as he would do later on CNN. He was sitting in Pumpernik’s, a Jewish deli in Miami, interviewing whoever happened to have walk through the door.

His guests were waiters, tourists, and a plumber with whom he had a 45-minute conversation.

King has gone on to conduct over 30,000 interviews across his 60-year career. He built a legacy by asking questions and letting his guests respond. He’s not renowned for his oratory skills, his writing, or his investigative chops. He’s known simply for his ability to ask and listen.

Sounds simple in theory, but it’s extraordinarily difficult in practice.

Interviews with sources should play a central role in any content marketing strategy, but there’s no sugarcoating it: mastering this skill is a difficult thing to do.

Interviews with sources should play a central role in any #contentmarketing strategy, says @FSUAndrew. Click To Tweet

Why interviews matter

One of the first things to go in a world of churning more content more quickly is quotes from sources to support the content’s thesis. Too many content marketers rely on their own opinions and experience. They likely have trouble sustaining an audience because they provide no diversity of perspective, no point-counterpoint model to establish authority.

Want proof? Look no further than media that have lasted the test of time. You’d be hard-pressed to find an article in Esquire or Rolling Stone that didn’t contain quotes from an interview subject. It’s basic journalism. Some of the most-celebrated magazine articles of all time are profiles of compelling characters whom the writer spent hours interviewing and observing.

In the age of content snippets, this type of journalistic writing can feel absent from brand publishers.

But it shouldn’t be.

“It’s fine to assume that you are the subject-matter expert for a given piece, but even then, your audience gets a more diverse, more informed piece when you talk to actual sources,” says Jay Acunzo, founder of Unthinkable Media. “The reading experience is richer, and the information is much more well-rounded.”

Interviewing sources is a tricky skill to pick up, though. The best way to learn is through repetition, but it sure helps to have some advice. And for that, it’s best to look to those who have been doing this kind of work for decades.

4 principles of interviews

Stephen D. Isaacs, a prominent journalist and professor at Columbia University, laid out Four Principles of Interviews in his teaching:

  1. Prepare carefully, familiarizing yourself with as much background as possible.
  2. Establish a relationship with the source conducive to obtaining information.
  3. Ask questions relevant to the source that induce the source to talk.
  4. Listen and watch attentively.

You can see echoes of each of these principles in every legendary journalist, from Larry King to Lester Holt.

Let’s dive into each principle and see what some renowned print, radio, and television journalists say about applying them to interviews.

Prepare carefully

American Public Media’s Marketplace has a challenging task: explaining complex economic issues to everyday Americans.

You can’t do that unless you prepare.

“Rule No. 1 for me is preparation. Know everything you can – or everything you have time to study – about what or who the subject of the interview is,” says host Kai Ryssdal. “From there everything just sort of happens.”

Being well versed on the topic lets you ask more intelligent questions that cut to the heart of the issue rather than pose basic questions that elicit answers readers could find anywhere. Knowing your facts also helps when an interview subject tries to dodge a question or states a falsehood.


Image source: Photo source: LynnGilbert5 (Wikipedia Commons), CC BY-SA 3.0

Prep work should involve studying not only the interview topic but the interviewee.

Prep work should involve studying not only the interview topic but the interviewee, says @FSUAndrew. Click To Tweet

Barbara Walters, another interview virtuoso, never cuts corners when it comes to research.

“I do so much homework, I know more about the person than he or she does about himself,” the career journalist says.

Surprisingly, King takes the opposite approach. Check out this tidbit from a 1980 People Magazine profile:

 Remarkably, however, he never prepares for a guest. ‘This way the audience and I can learn together,’ he explains. ‘I never ask a question when I know the answer.’

While certainly not a best practice, King taps into an important factor that makes interviews compelling for your audience – throw out the jargon, and make it conversational. Studying the topics and people helps the conversation flow more naturally (unless you’re Larry King).

Establish a relationship

Equally important to a natural-feeling conversation is establishing a rapport with the interview subject.

“On my podcast, I need guests to tell a detailed story, not give platitudes,” says Acunzo. “I need them to speak freely with emotion, not sound like a robot.”

Interview guests should speak freely with emotion, not sound like a robot, says @jayacunzo. Click To Tweet

The challenge is getting the interview subject to break away from their rehearsed, boilerplate answers. It’s natural (and understandable) for people to enter into an interview with an agenda they want to communicate – it’s likely why they agreed to be interviewed in the first place. The problem is, this makes for incredibly dry, boring material.

Subjects can still communicate what they want while putting forth a compelling story about the topic. But again, that responsibility lies on the interviewer, not the interviewee.

“Don’t be afraid to interject and play the confused party,” suggests Acunzo. “You want to sound interested, not annoyed, like you need clarification, even if you really just ask the next question or steer the conversation back your way. But you have to be comfortable jumping in.”

Building an initial bond can make that process easier. Acunzo’s secret weapon for getting guests to open up? He asks one question – do you have any pets?

Once the subjects warmly talk about their fur baby or childhood pet, or why they don’t have a pet, they’re speaking freely and unrehearsed.


Image source: U.S. Army, CC BY 2.0

Lester Holt, anchor for NBC Nightly News, has a perspective that helps build rapport:

 My approach (when reporting) is that could be my town, that could be my house, my loved one at the center of that story, and how would I want to be treated at that moment? In my opinion, there is a lot of room for compassion in what we do.

While Holt speaks about reporting on tragedies, the lesson is still applicable to content creators – approach your interview subjects with compassion and attempt to see the situation (whatever it may be) through their eyes.

Ask relevant questions

Questions provide the substance of an interview. Whether your source provides interesting responses that engage your audience or dull responses that you can’t use comes down to the questions you ask and how you ask them.

There’s a temptation to apply age-old networking advice to interviews and only ask open-ended questions, but as Isaacs mentions in his Four Principles guide, both open- and close-ended questions can be useful.


Image source: U.S. Department of Defense, Public Domain

While an investigative journalist must ask cutting questions that dig into important issues, content marketers may be better served by taking the Larry King approach: short, simple, and unassuming questions.

 Simplicity worked for me … and I’ll tell you this: I never ask questions over two sentences long. I watch some of these presidential press conferences, and (the reporters) are showing off. And for what end?

Content marketers may be better served by asking short, simple, unassuming questions, says @FSUAndrew. Click To Tweet

King uses the kind of simple questions infrequently asked of his guests. Many of these provide opportunities for guests to share an introspective look at their work, which makes for more compelling material. He uses questions such as “What’s it like,” “What do you think about,” or “What if you’re wrong?”

Everybody usually asks or thinks about these questions of themselves but rarely are asked in an interview setting. These unexpected questions also let guests break away from their rehearsed answers.

Many times, you won’t elicit the best response with the initial question. You’ll need to ask follow-up questions. As Acunzo says, “If you don’t get what you need in your first stab, be prepared to say something other than, ‘Makes sense!’

He suggests asking questions such as:

  • Tell me about X.
  • Can you share an example?
  • You guys did X instead of Y. Deciding to do that must have been hard. Take me into the room where you made that first decision. Who was there, and what was going through your minds?

Listen and watch

When interviewing someone, your mind often has an internal dialogue going too – is the recording working, what should I ask next, how do I spell that word they just said.

That’s understandable; you want to make sure everything goes smoothly. But if you’re not listening to what your subject is saying, you’ll miss the clues they’re giving to inform your next question.

“Whatever else is happening in the studio, or in the field, none of it is of any concern to the listener,” says NPR producer Paul Ingles, “which is why you have to force yourself to listen harder because some part of your brain actually does have to manage that other chatter. But if you can’t learn to manage that chatter and listen better, you won’t be doing your best work as a reporter.”

Attentive listening and watching also can help you paint a picture for readers or listeners. People don’t want to read a dry back-and-forth conversation between two people; they want to visualize the setting in their heads, as if they were sitting with in the room. What’s the tone of voice? What’s the room like? What is the person wearing? These observations can make the material more vivid.

The story is on you

Not long after starting his show from Pumpernik’s Deli, Larry King scored his first celebrity interview when singer Bobby Darin walked into the restaurant for breakfast.

“All I knew about Bobby Darin was (the song) Mack the Knife, so I asked him, ‘Where did Bobby Darin come from?’” King explains in a Chicago Tribune retrospective.

From there, King’s simple style was born. Though often criticized as being too soft on his subjects, it’s hard to deny that King found a style that worked for him and pulled stories out of his guests in a way that connected with audiences.

And that’s ultimately who he’s accountable to, as are we as content marketers.

“You are responsible for the story delivered to the audience,” says Acunzo. “If a guest isn’t charming on a microphone or replies to your email with a canned response, that’s your fault, not theirs. You are the boss of the recording, the shoot, the article. Be kind, but act accordingly.”

Content marketers are responsible for the story delivered to the audience, says @jayacunzo. Click To Tweet

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Cover image by Joseph Kalinowski/Content Marketing Institute