3 Interview Questions Every Show Host Should Ask to Capture Irresistible Material
Stop me if you’ve been here before: You’re interviewing a guest for your podcast or video show, and your guest just isn’t giving you what you want. Their answers are meandering and punchless. They keep elevating to generalities when you really want specifics and stories. You’re breaking out in cold sweats.
Seriously, stop me if you’ve been there before.
No, like, for real: STOP ME. Or better yet, stop your guest! See, if a guest isn’t giving you great material for the final episode of your show, it’s not their fault.
I was recently chatting with marketing showrunner Adam Rogers of Shopify. Adam is a newcomer to the Marketing Showrunner community (welcome, Adam!), and he brought with him a tough problem: When it’s on US to deliver great content, but so much of it comes from the guest, what can we do as interviewers to get better material for our episodes? Whether we create narrative, docu-style episodes or publish irresistible interviews, what questions can we ask our subjects such that they respond with pure gold … instead of yet another turd we need to polish?
Over the past few years, I’ve run the gauntlet by interviewing hundreds of executives, entrepreneurs, creators, and practitioners from all walks of life, sometimes on my podcast, Unthinkable, sometimes on client projects in video or audio, and sometimes on stages as a keynote speaker asked to moderate panels. In every case, it’s my job as the host (or moderator) to care about the final experience delivered to the audience. If they love it, everyone else involved wins.
Unfortunately, in every case, there’s just one thing that my interview subjects had in common: they aren’t producing the content along with me. At no point in their minds are they giving answers while also shaping the experience proactively, but with every answer they give, they shape the experience. It’s quite the conundrum, and when you interview people in the business world, it can get even harder, as they often have all kinds of marketing soundbites and agendas swirling in their brains. (Hence why I called my interviews “running the gauntlet.”)
In the end, it’s on me as the host and interviewer — and on you too — to figure out the right questions to ask in the right order to extract great content.
Here’s how I think of it:
You’re Not an Interviewer. You’re a Dance Partner.
The most important thing to do is mentally frame your interviews appropriately. After all, what are interviews really for? Getting the guests to say something the audience cares about, right? As an interviewer, you’re in extraction mode. That often means revisiting and reworking a moment or idea, asking the same question different ways, or asking guests to fill in gaps without pointing out that their initial answers were weak.
As a result, a great interview isn’t a constant march forward. Instead, think of it like a dance. There are some steps back, steps forward, steps to the side — all packaged together in one coherent experience, with lots of zig-zagging and subtle steps inside those boundaries. The pattern needn’t make sense to your partner, because you know every move. In this dance between interviewer and subject, you’re leading them where you want them to go. Period.
If the guest starts to meander too far to the left, your job is to gently (and sometimes not-so-gently) coax them right. If they begin to stumble, help them get back on their feet. If they aren’t comfortable dancing, you need to find ways to loosen them up.
There are dozens of tactics you could deploy to achieve any number of these things. For instance, to loosen up a rigid guest, I often say, “I’m gonna hit record, but I’m gonna take this first part out. I just want to check your levels really quick on my end, so here’s a random question: Do you have any pets?” They often laugh and describe their furry friends at home. If they say no, I ask why, and there’s always a story about a past pet, or they go, “Well, I have three kids! That’s enough, right?!” You’d think I’d never heard that answer before, I laugh so hard.
While I tell them that I’m engineering their levels, or some other technical jargon, the truth is, I’m not. In reality, I’m engineering them.
The dance continues. They feel comfortable enough to take my hand, clasp my shoulder, and begin to step. Now it’s my responsibility as a host — and yours — to guide them so this dance is worth watching (or hearing). So what’s the best way to do that?
Ask really great follow-up questions.
Everybody Has a Plan, Until They Get Punched in the Face
I believe Mike Tyson said that about boxing, and at the risk of mixing metaphors (boxing is kinda like dancing, no?), I think we rely too heavily on planned questions as marketers. On our best days, we like to write down a clever list built on research and cling to them like religion. On our worst days, we trot out the same old questions as every other episode. Either way, we’re missing the true power of an interview: asking great follow-up questions. We need to be ready to ditch our plan the moment something surprising, interesting, or just plain better crops up. Likewise, we need to master the art of follow-ups for those moments where our interview subject begins to meander or sound like a PR soundbite machine.
You could ask an infinite number of follow-up questions, of course. It all depends on you, the subject, and what you’re discussing or what’s said. But it’s possible to deploy a series of three crucial interview questions to capture irresistible story details. Two of these are follow-ups. The key is to ask them (A) in order and (B) only if you need a given question, because the previous answer didn’t cut it.
Here’s the string of questions as I ask them:
First, ask open-ended questions:
“Tell me about X” gets you story details, while “how did it feel when” gets you key moments of reflection and analysis. Both are crucial. Regardless, your first step in this interview/subject dance should be an open-ended question. Give them the chance to tell the story, or reflect on it, which enables you to then focus all your follow-up questions on more logical questions you authentically think of in the moment, in order to fill in the story. (These are things not listed in this post because it’ll feel like a natural conversation, like, “So what happened next?” or, “Wait, you said Melissa. Who’s that?”).
However, sometimes, when you ask an open-ended question to start an interview or a section of the interview, you don’t get a chance to follow-up about the story details specifically … because they never get to the story in the first place. Sometimes, as with many executives or business people, they launch into the atmosphere, giving you a 30,000-foot view or a generality to try and sound smart, or to avoid exposing the brand to any potential vulnerabilities publicly. But those answers are so. damn. blah.
For instance, if I ask a founder, “Tell me about acquiring your first 10 enterprise customers,” they might respond with, “Well, I think in general, when you’re early in your startup’s growth…”
Ugh. I’ve lost them to generalities. I want the story details. Gimme the goods!
Here, it makes sense to go to my first follow-up when an open-ended question doesn’t work:
Second, ask for an example:
It’s that simple. Just say, “Can you give me an example?” If need be, let them know they can take time to think about it, and you’ll edit out their pauses. Regardless, simply asking for an example can yield magical answers. It’s nicer than saying, “Yeah, yeah, yeah, I get the generality, but let’s focus on specifics.” But they can still take the hint: Oh, right, I need to share actual details.
Even still, some guests escape this question without saying anything of value. They give confusing answers that sound promising to start but lack the final oomph of a great story, or else they once again respond with a generality. For instance: “Okay, so, when we wanted to acquire our first enterprise customers, we relied heavily on thought leadership. Yanno, in today’s noisy world, where the buyer has all the power…” Oh boy. I’ve lost them again. We might be dancing, but they’re leading me to where I don’t want to go: mundane content. (Maybe that’s, like, a high school slow dance, swaying back and forth without aim? Let’s just move on before the metaphor trips us up. Kinda like me on the dance floor trying to pull off literally any move aside from swaying back and forth…)
When a guest fails to respond with a great example, we can rely on one, final, special type of follow-up question before deciding to move on entirely. Give it one more stab to get the goods.
Finally, “put them in a box.”
If the open-ended question AND your attempt to get an example still don’t yield great material, try painting a picture of a very specific scenario, then asking for the next step in that scenario. I call this “putting them in a box,” because I’m building the walls of the box for them, giving them A, B, C, and D, before leaving one side of the box open for them: “So what was E?” If they want to escape the box, they’ve got no choice but to go in the direction I want.
Back to our entrepreneur acquiring enterprise customers. As a final attempt to get that story, I might say to them: “Okay, just so I understand: You didn’t have any funding or revenue, so I’m sure you had to find organic ways other than ads to acquire customers. You knew publishing thought leadership would help cut through the noise, and so now you have to publish … something. So what was the first thing you published, and who created it?”
It’s the most specific, focused question I’ve asked thus far. It’s my attempt to get a detail, any ONE detail, from a tough guest. I can always keep asking for the next few details afterwards. Best of all, even if my assumptions were wrong in constructing the box, they can correct me with, you guessed it, details! “Actually, Jay, now that you mention it, we did have some funding. We raised an initial round from family and friends, and so we could use advertising like Facebook and Instagram.”
Great! “So what kind of ad did you run on Instagram? Seems like a place you don’t normally reach enterprise customers. What content went in your ad specifically?”
Look, I get it: We all want to build rapport with the guest. It can be hard to push back if they’re not giving you what you need to create a great episode. So don’t push back. Follow up! Without allowing time to do so, you skim the surface and thus create a superficial show — easily copied, easily lost in the sea of sameness out there.
Simple questions often yield the best answers, but the key isn’t to stick to a list of preconceived questions no matter what. The key is to prepare for what follows, once they answer those questions … but didn’t give you what you need.
Often, a guest can steamroll our interview until we’re left with some meh content for our audience. In that scenario, nobody wins: not them, not you, and not the guest. While initial questions help point our guests in a direction, as hosts, we can rely on our follow-ups to ensure we get the best possible final episode.
Remember: You’re not an interviewer. You’re a dance partner.
Just make sure you’re the one who leads.
Founder of Marketing Showrunners, author of Break the Wheel, and host/producer of docuseries about creative work. I’m a believer that exceptional work happens when you find and follow what makes you an exception. Previously in content marketing and digital strategy at Google and HubSpot and VP of brand and community at the VC firm NextView. I write, tinker, and speak on stages and into microphones for a living. It’s weird but wonderful.
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