The Power of “Hard Working” Questions in Podcasting


The difference between a podcast interview that sticks in the listener’s mind and rattles around for weeks and the one that gets lost in the great wash of content often comes down to the questions that are asked.

Some questions are like a soft toss—easy to answer, requiring little thought from the guest. But then there are the “hard-working” questions. These are the ones that make your guest pause, think, and dig deeper. They provoke insight, evoke emotion, and sometimes, they bring out stories or perspectives that even the guest didn’t know they had in them. 

These are the moments when your audience leans in and really listens.

There’s no magic formula for crafting these kinds of questions, but there are techniques that professional interviewers often use. I reached out to a few expert question-askers to get their take on what makes a question truly hard-working.

Jesse Brown, the host and publisher of Canadaland, doesn’t believe in having boilerplate questions that work in every scenario. His interviews are often about accountability, not connection—something most organizations might shy away from. But Jesse does offer a technique that can work in any context. He says,

“If I’m having trouble getting them to speak off the cuff, I might describe to them a way of looking at things that I know contrasts with their own, and then ask, ‘What part of that is wrong?’”

This approach pushes the guest off their rehearsed script, making them think on their feet. It also introduces contrast between viewpoints, which can sharpen and clarify their response, bringing it into crisper focus.


Dominic Girard is a brilliant producer who has worked at CBC and Pacific Content, has a different approach. Dominic suggests paying close attention to the small details your guest might casually drop—what he calls “following the breadcrumbs.” 


He recalls a time when a guest mentioned in passing, “I had a can of bear spray with me that my husband wouldn’t let me leave without taking.” 

For Dominic, that throwaway line wasn’t just about the bear spray—it hinted at a deeper story about the guest’s relationship with their husband, or perhaps their own approach to safety and organization. You might follow up with a simple question about the husband, “Tell me more about that, is he the careful one in the relationship?”  Or, “What was your response when he insisted on this?”  As Dominic says, “Could be nothing. Could be a sweet gem in there.”


Dominic also advises adapting your questions to the guest and the story you’re looking to draw out. Sometimes, “How did that make you feel?” may not get the best response. Instead, try “What did that make you think?” or “What was going through your mind at that point?” Some guests might not be as emotional as you’d expect, but they’re great thinkers. So you need to adapt to them: meeting them where they are can unlock a deeper, more insightful conversation.


Kathleen Goldhar is the host of CBC’s Crime Story and producer of the investigative podcasts:The No Good, Terribly Kind, Wonderful Lives & Tragic Deaths of Barry & Honey Sherman and Do You Know Mordechai offers a deceptively simple question: “What’s at stake?” 


Whether it’s “What’s at stake if this doesn’t happen?” or “What’s at stake if this does happen?” She says this question always makes her guests pause and think deeply before answering. 


“Every time I’ve asked it, they stop and think—they don’t answer it automatically, which makes me think it’s a good question.”


Kathleen also emphasizes that the most important thing a host can do isn’t just to ask a great question—it’s to listen very closely. Active listening is how you catch those breadcrumbs—the subtle clues that can lead to the heart of a story.


Personally, I think the most powerful question in storytelling is maybe the simplest: “And then what happened?” 


So often, interviewers miss the opportunity to help a guest walk the audience through their experience. Keep asking it until the narrative story unfolds. When I trained audio journalists at CBC, I would say, only half-jokingly, the perfect interview has just three questions: 

  1. What happened? 

  2. And then what happened? (repeat until story completed)

  3. What do you think about what happened? 


It rarely plays out this way, but if it did, you’d have the perfect story.


Lastly, very often, the best question is silence. Sometimes the most effective way to draw out an additional reflection or to get the guest to reveal their real feelings about something is to simply pause for a few beats. Resist the urge to fill the silence with your own thoughts or the next question. Every now and then, let the guest do the work of breaking the silence.


Hard working questions are not about tricking your guests. This is not about creating a ‘gotcha’ moment. Instead they help the guest connect with the audience. Every guest has the same goal as every podcast interviewer, they want to be memorable. Hard working questions help your guest, and your podcast, stand out in a very crowded content universe.