Podcasting Tips for Authentic Conversations

A client preparing for an important podcast confessed he's a bit "wordy." I complimented him for recognizing what could be a fatal flaw and said, "That's why you're going to keep your remarks to 2 minutes and answer every question with an EXAMPLE instead of an EXPLANATION. Explanations are INFObesity. Examples are INTRIGUING." He agreed but said, "I don't know HOW to tell a short story." I told him, "The key is to put us in the S.C.E.N.E. Here's how: S = SENSORY DETAIL: Start with WHERE to put us THERE. Think of a real-life situation that illustrates your point. What did it look like? Smell like? Feel like? Sound like? C = CHARACTERS: Describe the individual(s) involved so we know their MOOD. We don't need to know they have brown hair. The question is, are they sad, mad? Excited? Frustrated? E = EXPERIENCE IT: Re-enact what happened so we can SEE what you're SAYING. If YOU see and feel what you saw and felt then, WE will too. N =NARRATIVE: If you don't have dialogue, it’s not a story, it's a listicle of events. Use comma/quotes of exactly what was said so it's ALIVE and we feel part of the conversation. E = EPIPHANY: What is the lesson-learned, shift, or AHA where everything comes together and the point suddenly makes sense? If the podcaster asks, "WHY did you write this book?" don't TELL him why you wrote the book. Put us in the S.C.E.N.E. of when and where you realized people were getting outdated badvice, and decided to share your recent research and evolutionary results so they could thrive instead of suffer needlessly. And keep each response to under 2 minutes. If you do, this becomes a rock-and-roll interview from start to finish. You will be infinitely more interesting and people will be motivated to keep listening. #podcasts #storytelling #speaking #samhorn #presenting

Filmed my first in-person podcast yesterday. It went OK; perhaps half the discussion was good. I've wanted to start a podcast for years, but actually filming one taught me so many lessons that I never would've picked up otherwise. It made me appreciate the Dwarkesh Podcast interviews much more. Some things I learned: 1. The first question is the most important. Find common ground with your guest as quickly as possible; ask a question that you both care about. 2. There is only so much research you can do on a guest from reading their work. Sometimes discovering the most interesting things that they're thinking about requires that you have dinner together first. I'm going to do this with future guests; a discussion before the discussion. 3. Throw out most questions. I spent ~25 hours researching for this interview (it was with Michael Nielsen) but figured out, partway through, that I had scoped out too many questions in too many categories to do any one idea justice. I should've narrowed the entire interview to a single big idea, like Creative Identity or "Why biology doesn't have a strong tradition of theory compared to physics," and so on. We easily could have talked for 1.5+ hours about either of those, but I skipped around too much. 4. Building context is important. In the recent interview between Dwarkesh and Michael Nielsen, Dwarkesh opens with these really nuanced questions about the Michelson-Morley experiment and these seminal experiments in physics. This slowly builds the *context* required for his "big" thesis; namely, how do we recognize scientific progress when we see it? That big, open-ended question will only work if you've already built up this context! Dwarkesh thus goes into the interview with a specific question, but spends a great deal of time first building up the context for it. This is really masterfully done, and I didn't appreciate it before. 5. Many of my questions ended up being too open-ended -- and thus didn't elicit great conversation -- because I hadn't already built up the context. 6. Lights are really, really important. Cameras and microphones are not enough! 7. After the interview ends, take a pause and think about the discussion. Then, as the interviewer, ask your guest if they'd be willing to go back and revisit some ideas. The interview doesn't need to be entirely linear; you can learn from the discussion, end the podcast, and then film more segments afterward to fill in gaps. This often yields the best clips, too, because you're more relaxed and not thinking, "Oh shit, this is a real interview and I need it to go well." The interview has already ended, and now you're just chatting as friends. Many more lessons on equipment, setup, interview prep and note taking, etc. I'll plan to write these up as I begin publishing the interviews. I'm determined to get much better.

5 things that will transform the way you connect—on camera, in meetings, and in real life. After 12 years in journalism, I’ve learned that connection has less to do with how well you speak—and more to do with how well you see the person in front of you. Whether I’m leading a podcast interview, navigating a hard conversation, or just catching up with a friend, these five habits have made every interaction deeper, clearer, and more human. My five game-changing interview strategies that work beyond journalism: - Listen beyond words - Body language and pauses reveal more than perfect answers ever will - Embrace the awkward pause - Count to five after they answer. The magic happens in that silence - Ask open-ended questions - "How did that make you feel?" beats "Were you sad?" every time - Watch for emotional cues - Fidgeting, voice changes, and hesitation tell the real story - Practice emotional breadcrumbing - Reference something meaningful from their past that shows you truly see them The most transformative technique? Finding that Instagram post from three years ago about something deeply personal that never made headlines. When you show someone you've done real research into what matters to them, walls come down instantly. These skills revolutionized my podcast conversations and everyday interactions. Whether you're leading a team meeting, having a difficult conversation with a partner, or building new relationships, better questions create deeper connections. Study the masters: Oprah for emotional intelligence, Terry Gross for elegant questioning, Jon Stewart for navigating sensitive topics with empathy and humor. The goal isn't just better interviews—it's becoming someone people feel truly heard by.

I hate speaking to people but I still went on a podcast anyways. Amber created something special with Off The Record. It's a space where lawyers get to show up as actual humans. Not polished. Not scripted. Just real conversations about how you think, what you've been through, and what shaped you. Here's why more lawyers need to do this: 1. It Humanizes the Profession People hire people, not resumes. Showing up authentically builds connection and trust. Why It Matters: • Clients want to know who you really are. • Vulnerability creates deeper relationships. • It breaks the cold lawyer stereotype. 2. It Sharpens Your Thinking Talking openly about your journey forces you to reflect. You process lessons you didn't even know you learned. Why It Matters: • You grow by articulating your story. • It helps you understand your own path. • Reflection builds clarity and confidence. 3. It Inspires Other Lawyers When you share your struggles and wins, someone else sees a way forward. Every type of lawyer out there has a story worth telling. Why It Matters: • New lawyers need to hear real stories. • It normalizes the hard parts of practice. • Your experience becomes someone else's encouragement. 4. It Builds Community Real conversations create real connections. This is how you find your people in the legal world. Why It Matters: • Strengthens professional relationships. • Opens doors you didn't expect. • Creates a network rooted in authenticity. Some incredible lawyers have already been on the show. Catch episodes from Kurt London, Tony Albrecht, Tim Semelroth ★★★★★, Ryan Hancey, and Sharif Gray, Damon Hudson. (sorry if I missed anyone) Every single one is a great conversation worth your time. Reach out to Amber DiCarlo, MBA and get on the show. Show up as yourself. That's all it takes. P.S. If you're a lawyer sitting on the fence, stop waiting. Your story matters more than you think.

When I started hosting my podcast, I thought the biggest value would come from asking good questions. I was wrong. The real learning came from listening , again and again across dozens of conversations with leaders, founders, and educators. Here are a few lessons that stayed with me: 1. The most experienced leaders don’t rush to sound smart They pause. They think. And they’re comfortable saying, “It depends.” That restraint is usually backed by years of seeing things go wrong. 2. Real insight shows up after the polished answers The most meaningful moments often come after the formal response when people share what didn’t work, what surprised them, or what they’d do differently today. 3. Everyone is solving a people problem, not a technology one No matter the role or institution, conversations always circle back to trust, clarity, and alignment. Technology is just the tool around it. 4. Good leadership is quieter than it looks online The leaders making the biggest impact rarely talk about disruption. They talk about responsibility, consistency, and decisions that hold up over time. 5. Listening regularly changes how you build Hosting these conversations made me more deliberate as a founder. Less reactive. More thoughtful. More aware of second-order effects. The podcast didn’t just give me a platform. It gave me perspective. And that’s something I carry into how I lead and build every day.

Why does the guy recording a podcast in his garage sometimes beat the Fortune 500 podcast with the big budget? It happens more than people think. After being involved in 1,000+ podcast episodes and working with some of the largest companies in the world, I've noticed something simple: The best podcasts feel like conversations. The independent creator in his garage naturally talks like a real person. It feels like you're sitting in on an interesting discussion — not listening to a presentation. So should Fortune 500s just give up? No!!!! They actually have a massive advantage — if they use it right. Inside great companies are Key Thought Leaders who: • see industry trends before anyone else • work with fascinating partners and customers • have incredible stories from building and running businesses That's exactly the kind of insight audiences want. But the format matters. Here are three things I often tell executives hosting company podcasts: 1. Think conversation, not keynote. The best episodes feel like two smart people talking about something interesting. 2. Share what you're learning in the industry. Audiences care far more about what you're seeing and thinking than product announcements. 3. Be an expert people can relate to. The best hosts are knowledgeable but human. Think Ken Jennings — clearly brilliant, but approachable. When companies get this right, something powerful happens. They combine authentic conversation with real expertise. And that's when a company podcast stops feeling like marketing — and becomes a show people actually seek out. What's a company podcast you think nails this?

Okay, yesterday I wrote that asking great questions is a superpower. It is. Today, I'll give you 12 tips I've learned from conducting 100s of podcast interviews the last few years: 1) Your guest mirrors your state If you're confident and open, chances are they will be too. If you're nervous and defensive, they probably will be too. Mindset is very, very important. 2) The goal should be a good guest experience An interview isn't an interrogation. It's a conversation, and my goal is simple: make them forget that we're recording at all. 3) Don’t worry too much about your audience This is specific to podcasting. I don't care about what my audience wants. I care about what I'm curious about. That's the only authentic way I can gauge what's interesting, and I can only hope that others find what i find interesting. The broader point is you don't want to be too self-conscious or self-aware of what you're doing. Focus on the subject. 4) Sailing > rowing Research is fine, but asking a pre-written list of questions in order is super lame and ineffective. I know you want a conversation to go in a certain direction, but trying to force it that way limits its value. You have to feel the wind to sail. 5) Argue with people who are too polished If you're getting stock answers, you can play devil's advocate and push them a little bit. This works with well-spoken people who have talking points. It doesn't work well with shy people. 6) State inaccurate opinions or numbers to trigger corrections Playing the dumb guy works with most people because then they get to play the smart one 8) Self-deprecate and ask dumb questions Re-emphasizing this point because it's particularly important to draw insights out of people who aren't interviewed often or are in their shell. 9) Ask a record skip question to get someone out of autopilot Sometimes I'll be in a line of questions about SEO and then just ask about architecture because I know they like it. They're like "wut?" and then their authentic self comes out, even when I go back to SEO. 10) The thesis emerges via the conversation You don't know what you don't know, and the patterns will emerge only if you're a mindful participant in the conversation. 11) Open up and be vulnerable You being vulnerable gives them the chance to do so as well 12) Double click and call back I'm shocked when I'm a guest on a pod, give an answer, and they don't ask any follow ups. No clarifications, nothing. We just move on...? Some of the best insights I've gotten come from "Can you explain more?" type questions. Also, if their eyes light up, come back to the topic. Notice body language signals. 13) Be confident This comes with time and practice, but the more confident you are, the more open you'll be to finding your own tactics, and getting away from a scripted playbook. Pros are fluid.

🎤 If all you do is share what you know, you'll be a completely forgettable podcast guest. 🥅 Not the goal. Don't put in all of that effort to get a podcast interview and then boot it when it's time to shine. Here's the truth: You could get on and just share what you know. But if that’s all you do, you’ll be forgettable. A total snooze-fest. 🫠 The real goal? Create a connection. With the host. With the audience. Not easy, but achievable with practice. What does that get you? Trust. Your written content has its job to do. This includes your LinkedIn posts and email newsletter. When these elements of your personal brand are super solid, that opens the door to finding your people, your ideal customer and making that initial connection. This is how you start to build an audience. Over time and with consistency, this is how you fill the "know" and "like" buckets. But "trust" is different. Trust takes time. But when you've taken the time to build trust, other things happen more quickly. When it’s time for a follow-up, or to introduce your offer, your audience doesn't react with "who is this person and how did they get in my inbox???" 👂 A podcast episode has space. Time. Ear access. Intimacy. That's where trust happens. But you have to deliver and connect with the listeners. At the Newsletter Marketing Summit in Austin, Chenell Basilio defined this kind of content as "Insanely Valuable Content," (IV content), that falls into one or more of these buckets: 1. Make money. 2. Save money. 3. Save time. 4. Make them laugh. 5. Teach them something (make them feel smart) While she was referring to newsletters, the same is true of podcasts, YouTube videos and anything else you're building. Your content must be exceptional. Getting to "exceptional" is obviously a process. But here's how to start to make that happen in a podcast interview: ✅ Tell stories, not just strategies. People remember stories, not data dumps. Share experiences, lessons and even failures—be real. ✅ Talk to the audience, not just the host. It's not a private conversation and you shouldn't think of it that way. Especially risky for your C-suite. Instead, picture a listener driving to work or walking their dog—speak to them. ✅ Give, don’t gatekeep. Don't hold back your best insights. The more value you share, the more listeners will want to follow up & work with you. ✅ Have a very specific & clear next step. What should listeners do next? Connect on LinkedIn? Download something? Book a call? If you don’t tell them, they won’t do it. And you have to make it super simple for them to take action. 🎙️ Want tips on how to deliver in your next podcast interview? DM me "PG" for info on my media coaching. #mediatraining #PR #podcastguesting

Want to make a good podcast? Don't ask the same sh*t everyone else does. A lot of the guests I have on Stansplaining are quite well known so they have done lots of interviews. And they always get asked the same questions. Things about their career that interviewers assume everyone wants to know. But the feedback I've gotten from my podcast guests is that I don't ask the questions they're expecting. That's because I don't want to talk about the same things everyone else does. Why would someone listen to Stansplaining if they are just getting the same stuff they get everywhere else? These guests aren't 1 dimensional people, so I try to take a different lens and ask things I actually want to know. Because as I'm trying to get better at interviewing, I think the best way to do that is to find an angle I actually give a f&%k about. Asking them about how they make money and the business side of things gives me the chance to offer something to them as well. I'm not the guy that's going to give someone life advice, but I do know business, marketing, and content creation. So when we get into those types of conversations, I try to offer value back to them because I can speak to that stuff. Not only does that make all these podcast interviews way more fascinating for me, but it means the audience can see I know what I'm talking about. And it means hopefully my guests walk away with something they can use, too.

One of our clients recorded her first podcast episode last week. And afterwards she said something I didn’t expect: “I actually really enjoyed that.” Most first timers finish their first interview thinking about how they sounded. She finished thinking about the opportunity. Here’s why the episode worked out so well: → We prepared her message around demand, not delivery Instead of worrying about sounding perfect, we got clear on one thing: What problem is she known for solving and how does this interview highlight that? Keeping that angle in mind made her answers sharper and more relevant to potential buyers. → We picked the business stories that actually move listeners closer to a “yes” She didn’t share random anecdotes or a life timeline. She focused on the moments that explain why her work matters and the ones that build trust and open the door to sales. → We prepped her for strategic moments in the conversation The questions that reveal buying objections. The subtle openings to explain her method. The chance to position her offer without sounding pitchy. When she walked out, she said: “Honestly… I’m already excited for the next one.” And that’s what good business prep does: It turns a podcast from something you get through into something that actually drives demand.