By: Nancy Ryerson

There was a lot I loved about journalism school: finding my angle, getting the “lede” sentence just right, buying print newspapers for class on Wednesdays and working on the crossword puzzle before the lecture began (dreamy sigh). But the skill that’s come in handy the most in my content career has been the art of asking a question. 

It sounds simple on the surface. We ask questions every day. (Unless you’re a certain type of person on Hinge. You know who you are!) 

The stakes are high, though: in content marketing, like in journalism, getting the question right determines the fate of your final piece.

At the same time, approaching a conversation with a list of questions, checking each one off, and calling it a day doesn’t exactly lead to scintillating results.

That’s where the art comes in.

Do your homework, but don’t overdo it if your audience members aren’t experts, either. Be ready to follow the conversation where it goes, but know when to gently lead it back, too. Keep your subject comfortable, but press if you need to.

These days, I don’t generally approach random people on the street and ask them if they know that diabetes rates are increasing in their neighborhood, like I did in school (I sure was a fun college student).

Instead, I ask my questions behind a fancy podcast microphone, through my carefully perfected Teams filter, or sometimes just over email. But these same guiding principles to follow before and during an interview still hold true. So turn to a clean page in your little reporter’s notebook (dreamy sigh number two) and let’s get listening.

How to prep for a conversation

Do your homework, but remember that you’re not necessarily an expert, and that’s okay. Every question doesn’t have to be complicated. This was a trap I fell into especially in my first job at a medical trade magazine. I did not have a background in the subjects I was covering (also known as, I didn’t know what I was talking about), and at the time, I thought that was a big problem. So I almost over-prepared, asking questions that I didn’t even completely understand. 

Instead, plan to weave in big picture questions among more detailed ones. If you want, you can pretend that, of course, you understand, but what if someone was listening who didn’t? That’s a perfectly fair way to frame your question. Try something like, “How would you explain this to someone who’s new to [topic]?”

Remember that your question list is just a starting place. We’ve all heard corporate podcasts that sound more like someone reading a list of questions than like a conversation. Even for SME conversations that won’t be released as a podcast or video, a question list still isn’t the best way to dig up interesting content. 

By all means, brain dump a list of questions—but find the balance between leading and following the conversation, too. Sometimes I’ll highlight or asterisk my must-ask questions and glance at them before the interview is over to make sure I didn’t miss anything. 

Know what you want to get out of the conversation going into it. “Conversational” doesn’t mean talking aimlessly without a roadmap. For my podcast, writing a draft intro to the podcast episode helps me zero in on what I know I’ll want to focus on based on campaign themes, where I want to use the content, etc. 

Most people could talk to you about more than one subject. You don’t want to walk away with a list of spots you have to see on your vacation to Spain and miss the themes that are part of your larger content strategy. But do get those tips if it comes up—you can always edit them out in Descript.

If you’re asking questions over email, the pressure is on to choose the right ones. Emailing questions makes it more challenging to get interesting answers, but I want to believe it’s not impossible. Ask for favorite stories that bring their message to life, advice they would give their younger self, biggest misconception about their area of expertise, and of course, the classic, “anything else you would add?” 

Video responses are another technique I’ve used that gives you the async convenience of emailed questions, but leave more room for the unexpected. If you can go this route, I recommend it.

During the conversation

Repeat what you heard back to your subject. This can feel unnatural at first, but it’s a good way to pause for a moment and let the information sink in before moving on to your next question. This is also an effective approach to check your understanding and get a correction in real time, if you need it. 

Ask for a story. When a subject shares an opinion or a piece of advice, I love to ask if they have a story that illustrates their point. These moments are also great for clips afterwards, as they can often stand alone separate from the rest of your content. 

If you don’t understand—or agree—ask a follow-up. If you’re in content marketing, you’re probably not interviewing anyone with the goal of exposing a scandal. And if you are, wow! Please add me on LinkedIn and tell me all about it. But there still might be moments when you need to press on something that feels sensitive, or reveal your own ignorance of something in a way that feels vulnerable. Admit if you’re surprised to hear something or if you need clarification. Chances are, your listener is wondering the same thing.

Avoid multiple takes if you can. You may encounter leaders at your company who are naturals on stage but freeze up behind the camera. I think these people were most likely asked to do too many takes by a communications professional in their past, and it haunts them! I’ve witnessed well-meaning marketers strive to get that perfect sound bite on camera over and over until their subject started to sweat under those big bright lights. 

Your colleagues most likely aren’t trained actors. If they get too in their heads about exact phrasing, they’ll come across less human than you need them to. In our ~era of AI~, there’s nothing wrong with a few pauses or even a human laugh here and there (imagine that!)

The same goes for podcast interviews. It’s fine to mention retakes at the top of a podcast recording to calm nerves, but ideally, your subject will rarely take advantage of it. Too many re-dos gets your subject in their head instead of staying focused on the topic at hand.

Take notes during the conversation on points to come back to. In college and at my first job, I carried around those skinny reporter’s notebooks wherever I went. I wrote so quickly that people would ask me if I was using “shorthand.” I didn’t know what that meant but I would say yes anyway. (What is that??)

I still find that taking notes helps me listen better. Sometimes that looks like scribbling a single word on a piece of paper while keeping my eye on the screen during a podcast interview, but even that small act grounds me so I can find my way back if the conversation starts to head too far in the wrong direction. 

To list or not to list?

In the end, I might not really be advocating that you throw your question list away, after all. 

In fact, there might be something to having a handwritten, off-screen list to help escape digital distractions and focus on your subject. 

That’s what good listening is always about, anyway: focus. 

Stop thinking about your immediate next question and listen for that conversational thread that will teach you something new, give you that soundbite you can share on LinkedIn, and lend your content an ineffable human voice.

And maybe most importantly, you’ll start to hear that ultimate of compliments from your subjects: great question! ■

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Nancy Ryerson is a B2B content marketer who has spent her career covering healthcare. She’s currently crafting strategies and impactful pieces for Lantern, a specialty care platform, where she hosts the podcast Making Healthcare Sustainable. You can see more of her work, including a few pieces of flash fiction, in her portfolio.