How to Guide Unscripted Podcast Discussions

I realized that the best Superpath podcast episode ideas come from the community, not from us. So I've been following an (admittedly loose) process of teasing out discussions from the community that we can talk about on our show. 1. Notice a question comes up often in the community — a good signal that people care about the topic. 2. Share the idea with Jimmy Daly & Chloe Thompson (co-hosts) — I float the topic and see if it resonates with them too. If we're all virtually nodding along (or even better, we disagree with each other), we know it's episode-worthy. 3. Ask about it in the Superpath Slack community — I post the question to get an understanding of the "current state" of that topic. Sometimes I learn everyone is thinking along the same lines. Sometimes I learn everyone has a different experience. 4. Ask about it on LinkedIn — Sometimes I'll expand the net to get some extended viewpoints from folks outside our immediate circle. This also doubles as a bit of pre-promo for the episode and community, which is a nice bonus. 5. Prep the episode — I bin all the responses into themes and direct quote my favorite examples. It makes the episode richer and shows the diversity of thinking on the topic. 6. Record the episode — By this point, we're armed with real stories, different perspectives, and a clear sense of where the conversation should go. 7. Close the loop — When we publish, actually let people know we mentioned them. I need to get better at closing the loop here. If you've contributed to an episode and I haven't tagged you, my apologies. Consider this my public commitment to do better. I'd say this is all about the same amount of work as prepping episodes entirely on our own. But there's an added benefit from a business perspective: the Superpath Community (our product) and the Content, Briefly podcast (our content marketing) feel more connected in a closed loop. The line from content to customer becomes obvious. And I guess that's my job!

Two years and 50 episodes later, I still don't give podcast guests their questions in advance. Early on, Nick Paladino and I learned: if people know the questions (especially if they're nervous), they write out answers. Then they read them. And it sounds exactly like someone reading prepared answers. We give them ONE question ahead of time. The same one we ask everyone. And guests still act surprised when we ask it on air. The spontaneous conversations are always better. More honest. More interesting. More human. Same goes for internal meetings, client calls, and pretty much everything else. Stop scripting the life out of your conversations.

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.

In podcasting, I often talk about understanding the dynamics of an A and B conversation. By this, I don’t mean just the mechanics of conversation, but literally knowing who is A and who is B. In a chat cast, where both hosts share equal weight and responsibilities, it’s crucial to know when to lead and when to react. In successful chat casts with at least two hosts, you'll notice a few markers of balanced A and B conversations. Usually, one person leads by welcoming listeners, introducing the show, and presenting the topic. The other person then provides reactions, hot takes, or moments of levity, turning the monologue into an engaging exchange. Achieving this balance requires understanding the natural flow of conversation between the hosts. Whether you're friends, colleagues, or partners, observe how you naturally converse. Identify who brings up topics enthusiastically and who reacts more calmly or with humor. Knowing these dynamics helps in structuring your podcast effectively. In A and B conversations, it’s important to manage energy levels. If the person with big energy opens the show, the other’s calmer response might make the conversation seem flat. Conversely, two big personalities or two introverts need to find ways to keep the discussion lively and engaging. Understanding these mechanics means recognizing what each host brings to the table. By knowing your natural interaction style, you can design your show format to balance energies. For example, have segments where the calmer host leads and others where the more spirited host takes over. Build the topics progressively so that the conversation flows naturally and keeps the audience engaged. Ultimately, knowing yourself and being comfortable in your own skin is key. The more you understand your conversational style, the stronger your podcast will be. And that’s definitely something I can help with.

I've recorded 100s of interviews over the last 3+ years for various podcast. Here are some quick observations on how to ask your guests better questions: 1️⃣ If the person has written a book - read it. It's a courtesy and will give you things to unpack. Same goes for a newsletter or blog. 2️⃣ It's cliche but you have to listen. Like - really listen - to what they say. Fine to have a run sheet or script to follow but don't let it prevent you from following an unexpected tangent. 3️⃣ Field questions from your audience on social media in advance of the recording. "I'm interview X today - what should I ask them?" Harry Stebbings does this well. 4️⃣ If the person has a well-documented POV on something, you have to try and find a unique angle they haven't covered as extensively before. We all know April Dunford is the product positioning expert but I hadn't heard her talk that much about how her framework can be applied to service-based businesses. We discussed this on B2B Better Podcast and it's the most downloaded episode of all time. 5️⃣ Don't be afraid to be the dumbest person in the room. Ask guests to explain concepts to you as they would to a five-year-old. Curiosity is endearing. 6️⃣ Before any interview, you need to know what is the 'North Star' question we're trying to answer. This could come from the overall premise of the show or be guided by the guest you've selected. But there needs to be thinking around "here is what I want the audience walking away with" before any recording takes place. 7️⃣ When in doubt, open-ended questions almost always trump close-ended questions. "What is content marketing?" = boring "Why should we care about content marketing" = interesting 8️⃣ If you want specific answers it can help to contextualise questions with real-world experiences. For instance, sharing a story about how marketing attribution was broken in a company you worked for because no-one updated the CRM and then asking "how would we go about fixing that" may yield a very different answer to simply asking "how do we fix marketing attribution?" *** Larry King didn't become the GOAT interviewer from day one - it took 50,000 at bats over six decades. Like any muscle, you have to exercise the skill of asking questions regularly to get better at it. What tips do you have for asking great questions? #podcast #strategy #b2b

The Art of Hosting: Preparing for Conversations with Visionaries As a podcaster, TV presenter, radio jockey, and host, I have the privilege of engaging with some of the most successful, self-made, and well-read individuals—people who have experienced both wins and losses and are building legacies that will outlast their time. Meeting such remarkable minds requires preparation, not just in terms of research but also in terms of mindset. Here’s my approach to getting the best out of these conversations: 1. Silent Contemplation – Before any interaction, I sit in quiet reflection, allowing my fears and self-doubt to surface and pass. This helps me step into the conversation with clarity and presence. 2. Thorough Research – I read, watch, and listen to everything I can find—social media, press articles, websites, keynote speeches, interviews, and more—to understand their journey deeply. 3. Seeing the Person Beyond the Title – While their accomplishments matter, I seek to understand them as individuals—their values, experiences, and personal philosophies. 4. Preparing Questions That May Never Be Asked – I draft insightful questions well in advance, knowing that in a truly dynamic conversation, spontaneity often leads the way. 5. Embracing Free Flow – I remain open to the organic flow of dialogue, allowing unexpected yet meaningful threads to emerge. 6. Holding Space, Not Opinions – My goal is to facilitate expression, not impose my personal viewpoints. I ensure that the guest’s perspective shines through. 7. Tapping into Innate Wisdom – Every conversation is an opportunity to extract profound insights and keep discussions relevant to the audience and topic. 8. Staying Curious and Open-Minded – A great conversation stems from genuine curiosity and a willingness to embrace new and different perspectives. I feel deeply grateful to wear multiple hats, all of which revolve around knowledge, wisdom, and understanding the human experience. Every conversation is an exploration—an opportunity to learn, grow, and share something of value with the world. Watch out for my next episode with the gorgeous deepti sudhindra on The Whispers Of Wisdom Podcast . #wow #conversations #knowledge #podcast #host #presentor #humanexperience

Most B2B podcasts feature hosts and guests nodding in agreement. There’s no tension. And this is why the content can get boring. That’s why I like to play devil’s advocate sometimes. Whether you're hosting a podcast, conducting an internal interview with a subject matter expert, or gaining insights from customers, playing devil's advocate can lead to deeper, more meaningful conversations. But how do you present contrarian viewpoints without appearing argumentative? Here are a few things I like to think about before I go into an interview: ✅ Start with softballs: Warm up your interviewee with topics they're passionate about. Build rapport and trust. This part of the conversation doesn't even have to make it in the final deliverable — it's just important to building a foundation. ✅ Do your research: Nobody likes to have a deep conversation with someone who’s there to argue. Instead, gather information, get into the details, and prepare to have a thoughtful conversation with different perspectives. ✅ Don’t attack: Rather than going on the offensive with a different viewpoint, pose questions like “What do you think when someone says [opposite viewpoint]?” or “What’s the biggest issue with folks who feel [opposite viewpoint]?” ✅ Be curious: If you genuinely care about different opinions, it’ll come across in your interview. Creating tension during an interview isn't about being argumentative. It's about: - Encouraging deeper reflection - Exploring alternative viewpoints - Uncovering nuances in the interviewee's stance When it comes to interviewing or hosting a podcast, there's no one-size-fits-all approach. The fun part is developing your unique style that gets the best out of your subjects. What’re some of the things you do to have a well-rounded conversation?

Here are a couple of the rules I’ve made for myself for recording/prepping the Louder Than Words podcast… 💡No formal introductions: I’m trying to avoid guest autopilot at all costs. I’m going for natural/casual conversation…like you just happened to drop in on this convo. Nothing gets people into autopilot mode more than asking them to introduce themselves or “tell us a little about yourself.” If an intro is needed, I’ll use a story to disguise it, i.e., “The first time we got to know each other was when you were running marketing at….” 💡No general advice: This is a huge one for me. Instead of typical “how you…” advice, I’m going for personal “how I…” stories. I let guests know this up front…don’t show up looking to present. Instead, be open to sharing your own experiences. Be vulnerable. Don’t tell others what they should be doing…tell them what you are doing and/or have done. Let’s allow the audience to draw its own conclusions from there. 💡No podcast research: I don’t listen to guest’s past appearances on other podcasts. I don’t want to be influenced to ask similar questions and/or encourage them to tell similar stories they’ve already shared elsewhere. Instead, I dig into their work, past companies, etc., and allow my natural curiosity to drive my line of questioning. I want to ask questions no one else is asking. Listening to other podcasts doesn’t necessarily help me here. Jay Acunzo inspired me over the weekend when he texted me to compliment my recent interview/episode with Rand Fishkin. It inspired me to formally write down all of my “rules” for recording the kind of podcast I want. I’m sharing all of them in my newsletter this week. Link to subscribe in the first comment.