Ever find yourself staring at your podcast guest, thinking, “Okay, now what do I ask?” Same.

Some people have a natural gift for keeping conversations flowing and peeling back the layers of a topic. If that’s you, congrats—you’re living the dream. For the rest of us mere mortals, follow-up questions are a skill we have to build.

Personally, I get so wrapped up in what the guest is saying that when they stop, my brain goes blank. And let’s face it, “Uh… cool… so…” isn’t exactly a smooth transition. To save myself (and the conversation), I’ve learned to keep a few trusty follow-up questions on hand. Think of them as my safety net when the words don’t come naturally.

Now, these aren’t your typical prepared questions—the ones you send to guests beforehand to guide the interview. These are for those in-the-moment situations where you need to dig deeper, keep the conversation alive, and add to what Grenny in Crucial Conversations calls “to the pool of shared meaning.”

What’s the Pool of Shared Meaning? Here’s the idea: every conversation starts with two people bringing their own thoughts, experiences, and opinions—their personal “pools of meaning.” At first, the shared pool is tiny (especially if you’ve just met your guest), but follow-up questions help grow it, creating more understanding for you, your guest, and your audience.

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But before we get to the questions, ConvertKit (now just Kit), is getting ready to offer their once-a-year, super-duper, can't be beat, Black Friday offer. If you ever wanted to try it, I will have a link in next week's newsletter. Just giving you the head's up. 😁

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Okay, now for my five go-to follow-up questions that work like magic in any conversation.

“Tell me more.”

Okay, I know it sounds basic. You might be thinking, “That’s it? That’s the big trick?” But hear me out. When there’s a pause and you sense your guest has more to share, “tell me more” almost always gets them to open up. It’s like giving them permission to dive deeper, share that backstory, or add those juicy details they weren’t sure you wanted.

“Would you elaborate on that?”

This one’s a classic and a little more formal than “tell me more.” Think of it as your go-to when you want your guest to expand their answer—kind of like zooming out on a map to see the full picture. Sometimes, their initial response is the “I’m going to the store” version, but this question gets them to describe the journey: How are you getting there? Why that store? What’s on the list?

“What else?”

Simple, short, and surprisingly powerful. I picked this up from a mentor, and it’s quickly become one of my favorites. It’s especially useful when a guest has given you a good answer but you know there’s more under the surface. Just asking “what else?” can unlock additional thoughts and take the conversation in an unexpected direction.

“And…?”

Yes, this is an incomplete sentence—and that’s the point. Say “and” with a little pause afterward, and you’ll often get your guest to naturally continue where they left off. It’s an easy, low-pressure way to encourage them to keep talking.

Silence.

Ah, the power of saying nothing. I know it can feel awkward, but sometimes the best follow-up isn’t a question at all. Just give your guest a moment to sit in the silence, and they might surprise you by adding more on their own. Bonus: it also gives you time to gather your thoughts.

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Pro Tip: Keep These Handy

When I first started using these, I wrote them on a Post-It note and stuck it to my monitor during interviews. Now, I’m adding “What else?” and “And…?” to my list for even more variety. They’re lifesavers when you’re stuck or unsure how to keep the conversation moving.

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Wrapping It Up

Look, you don’t need to use all five in every interview—mix and match based on the moment. And if you can build a custom follow-up grounded in what your guest just said, even better. But when you’re in a pinch, these questions are your Swiss Army knife.

Try them out and let me know how they work for you. Or, better yet: what else? 😉

Till next time!

Eric Rutherford

P.S. How You Can Work with Me:

If you know you want to launch a podcast for your company or you have already launched one and want to outsource production, reply back and we will talk through what next steps look like.

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