Sometimes when interviewing experts to gain insights for your content marketing materials, it’s best to do something that, frankly, you might find a little off-putting. Marketing writers . . . you have to stop being so friendly sometimes and start asking obnoxious questions.

Okay, you’re thinking, just the idea of asking obnoxious questions puts me off. No one does business that way!

We hear you. Marketing writers should be all about putting out the shiniest, most professional content around — and you feel you can’t get there if you come off as obnoxious.

And yet being a little bit pushy with your domain experts can be the difference between creating the kind of overly-promotional content that is dismissed without a second thought and the meaningful content that sticks in a potential client’s mind — and makes them want to know more about your product or service.

More on this: Don’t Be A Clickbait-and-Switch Marketer

Marketing writers wearing journalist hats

At this content marketing agency, we often remind ourselves that the goal of good content is Robert McGuire calls the “unGoogleable.

““The whole point of content marketing is to be helpful to the reader, and any article that says what you can already find on Page 1 of Google search results won’t be helpful,” says McGuire. “Good interviewing skills allow you to find on what is in an expert’s head but not yet clearly articulated and indexed by Google.”

But once you secure those interviews, the original, unGoogleable content can still elude you unless you are willing to ask provocative questions.

There’s a whole crop of professionals out there who are well versed in asking obnoxious questions — who actually welcome the opportunity to do so. Who?

Journalists. In their training and work, journalists specialize in digging down below the surface of what people are saying — and in doing so, find out what they really mean.

Emulating the journalistic approach can be invaluable for your efforts as a marketing writer. By thinking like a journalist, you can find out some things that even your expert didn’t know they knew. In fact, a good interview helps the expert develop their own thoughts better, getting them to “realize” a new idea by confronting contradictions and complications.

But confronting contradictions and complications means you may have to be a tiny bit confrontational. It can be uncomfortable, but everyone will appreciate the more substantial material that results.

What journalists already know and marketing writers need to learn

“Experienced reporters have learned to go beyond their first instinct and push for an angle that has never been done or to do it in a unique way,” says McGuire.

Another way to think about it: obnoxious questions will get you past an expert’s elevator speech — and into what they really think about their area of expertise.

In fact, as Maria Wood’s piece on working with a ghostwriter explains, most of the value a ghostwriter provides isn’t in the writing itself. It’s in helping the author figure out what they’re trying to say.

Journalists have all sorts of clever ways to push — ways that down the road will lead to strong material. They know how to draw out an interview subject and get them talking about their area of expertise. Journalists will then pick up on things others might not recognize as important — and work in questions to get the subject to reveal something even the subject may not have considered important.

Often it’s not what a subject says in answer to prepared questions so much as what they say off-the-cuff — even if you both think the interview is over. A sharp journalist knows never to stop listening, and to follow up on anything that sounds even tangentially connected to the subject at hand.

Another helpful tip: linger around awkward pauses. Sometimes a question is met with silence, and an experienced reporter will feel responsible for filling it. Experienced reporter knows if they can bear letting it sit there, the next thing the subject says is more likely to be a new idea.

So what is a good obnoxious question?

Well, I should clarify. No need to lob weird insults at your interviewee. What we’re really talking about here is helpfully obnoxious questions. This is a tongue-in-check “grilling” that your expert source knows is valuable.

The sort of questions you want to ask depend on your strategic goals and, more immediately, what you hope to get out of each interaction with an expert. One way to think about helpfully obnoxious questions is that they sometimes look at things at a more basic level than you are accustomed — and then dig down deeper. Ask yourself: What questions would someone ask who knows absolutely nothing about my business?

More importantly, what sort of answer might they receive?

Put yourself in that person’s shoes. Think of yourself as a new hire at your company. What would you want to know about the company and the business they are in? Or imagine you’re a prospect hearing the company’s name for the first time. What essential information would you need? What are you skeptical about?

Push past the plug

Often, the first answer from an expert is a standard one. Some sort of plug for the company’s product or service. Right there is an opportunity to ask a helpfully obnoxious question: what is so special about your product or service? How is it any better than the competition? And can you give me some examples that demonstrate this?

Think of it this way: if the product or service makes so much sense, then everybody would be using it already, right? But they aren’t, so if you keep asking why not, you uncover complications, and when you start discussing those, you get to the good stuff.

If your expert is on the ball, they will recognize such questions as a genuine effort on your part to learn more — and they often will be happy to give you a more in-depth answer.

Once you become accustomed to asking helpfully obnoxious questions, you will find that experts are actually more eager to talk to you. These are the sort of questions that indicate a deeper interest in an expert’s field, which can lead to them telling you things they won’t tell anyone else.

This is how you get the ungoogleable content. This is how you create content that makes you stand out as a marketing writer.


Michael Ream is a writer and editor who has contributed to numerous publications,including Forbes, Saveur and Midwest Traveler. A former newspaper reporter, he earned a degree from the Medill School of Journalism at Northwestern University.