When you sit down with a guest on your podcast or conduct a live interview, you’re not just doing a Q&A — you’re opening a conversation. And the heart of that conversation is the questions you ask. Crafting questions that spark real connection, genuine storytelling and meaningful insights is what separates a so-so interview from one people remember.
1. Start with purpose — not just curiosity
Before you craft your list of questions, pause and ask yourself: What do I want this conversation to achieve? Are you looking for vulnerability, industry insight, or a personal story your audience hasn’t heard before? This shapes your tone, your depth and your approach.
For example: instead of “Tell me about your career journey,” try “What was the turning point in your career where everything changed — and how did it feel?” That subtle shift increases the chance of off-script storytelling.
2. Invite reflection with why/how questions
Open-ended “why” and “how” questions invite reflection and richness. Researchers note that questions structured around what, how and why encourage open dialogue and deeper responses. (EDUCAUSE Review)
Here are a few examples:
- “How did you arrive at that decision, and what surprised you about the results?”
- “Why did that experience matter to you in that moment?”
- “What was going through your mind when that event happened?”
These types of questions don’t just ask for facts — they ask for feelings, context, and meaning.
3. Layer the conversation — from surface to depth
Think of your interview as a journey. You might begin with lighter, comfortable questions (to build rapport) and then gradually move into deeper layers. Here’s one structure:
- Warm-up: “What does a typical day look like for you these days?”
- Mid-level: “What challenge caught you off guard this year, and how did you respond?”
- Deep dive: “Looking back, if you could go to that moment in your story and say one thing to yourself, what would it be?”
By building in layers, you give your guest time to settle in, and you open the space for unexpected insight.
4. Be prepared — but stay flexible
Good interview questions are grounded in preparation: knowing the guest’s background, recent work, and something unique you can ask about. But the real magic happens when you remain open to veering off your list when the guest gives you something interesting.
It’s worth noting that structured interview formats (with well-planned questions) tend to produce better outcomes — they reduce bias and increase the reliability of what you hear. (ResearchGate) That same principle applies in podcasting or any one-on-one interview: being intentional with your questions helps you get richer answers.
5. Listen actively and follow the thread
Your job isn’t just to ask the questions — it’s to listen for the thread worth pulling. Maybe your guest reveals a fleeting moment of doubt, or mentions a mentor off-hand. That’s your cue to dig in: “That moment you paused for a second when you mentioned your mentor — what was going on in your mind then?”
This kind of spontaneous follow-up takes you beyond your prepared list and into a place of real connection. And it signals to the guest that you’re truly listening, not just ticking boxes.
6. Avoid the obvious and the easily googled
As you prepare, steer clear of questions whose answers are obvious or easily found online. Asking “Is the company growing?” isn’t as effective as asking “What risk keeps you awake at night about the company’s next phase?” The latter is unusual, inviting, and specific.
According to guidance on interviewing, thoughtful questions show that you’ve done your homework — and that you’re sincerely interested in what the person thinks and feels. (astoncarter.com)
7. End with a moment of ‘what next’
Rather than ending with a standard “Any final thoughts?”, consider something more dynamic: “What’s the one next move you’re quietly excited about?” or “If you could peer into the next year of your work, what do you hope is different?” These wrap up the conversation by giving your guest forward momentum and something for the audience to anticipate.
8. Ready, set, record
Here’s a quick checklist you can run through before you hit record:
- Do I know one or two specifics about the guest’s recent work or experience?
- Have I drafted 3-5 core questions, each geared toward a different level of depth?
- Have I planned for follow-ups based on potential answers (e.g., “Tell me more about that.”)?
- Did I avoid questions that the guest could answer with a simple yes or no?
- Have I built in the possibility to pivot — if the guest says something surprising, can I explore it?
Why this matters for your podcast
At Premiere Podcast Pros, the goal is to create standout conversations that draw listeners in and make them feel like they’re in the room. By applying this playbook, you elevate your interviews beyond the standard. You give your guest space to share the human side of their story, and you give your audience something memorable, genuine and valuable.
Let Us Elevate Your Podcasting Journey
Ready to take your podcast on the road and grow your audience, and avoid the most common mistakes? With a well-executed podcast strategy, you can engage listeners, secure sponsorships, and expand your brand’s reach. At Premiere Podcast Pros, we’re here to guide you every step of the way.
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