Lessons learned telling 500 podcast stories

This year, I surpassed 500 episodes of podcast storytelling. Across my own shows (Unthinkable and 3 Clips), and current and former shows built for brands, I’ve learned a ton — it felt like going to the gym, but each time, I was sure I had nothing more to give.

I believe YOU have a lot to give. That’s why I’m working in private on a new online experience to teach podcasting, connecting small cohorts of makers and marketers to do actual work on their actual shows with a smart process and a lot of focus on fundamentals that most marketing content overlooks. That’s coming later this year.

For now, some lessons I’ve learned:

In interviews, questions to always ask:

Tell me about...

How did you feel when… (or, how did that feel?)

Can you give me an example?

Superlatives: Best, worst, funniest, scariest, hardest, least certain, favorite, etc...

Dig for emotional moments.

In reviewing tape, look for three types of moments as good quotes to use: 

Facts to understand the story (many can be voiced over if they drag on, so don’t overlook if they’re boring. Flag them.)

Reflections and emotions (the subject talking about how they felt — stuff you can’t get by googling or telling facts)

Conflict (the most important type of #2 — without conflict, drama, friction, etc., there IS no story, just case studies or descriptions of stuff)

And always ask, does this help advance the story…does it relate to the broader theme we’re trying to discuss? If not, kill it.

In scripting, ensure you’re ordering things correctly to win over listeners:

Establish the stakes early on (big questions, conflict, why someone would care, emotionally gripping moments left open-ended until later, etc.)

Build trust between audience and voices early (moments of laughter and warmth, pithy insightfulness, impressive career/achievements, etc.)

This then allows you to place more factual and potentially lengthier descriptions of what happened (or their advice) and the listener will give the benefit of the doubt that they’re worth hearing now.

In scripting VOICEOVER in particular, ensure you’re writing something to be spoken and heard, not something to be written and read

Short sentences, always. 

Keep it simple. 4th grade level. Speaking is so much less flowery than writing. Be visual and vivid, but without the advanced literature degree involved.

Constantly guide and tease the listener. 

Guide using “Sign posts” -- moments where you hint at something crucial they shouldn’t miss (e.g. “And that’s how Bill always viewed his work. Then one day, a man walked into his office.” Who’s the man? What did he say? You’re teasing the crucial moment, saying DONT miss what you’re about to hear. That’s a signpost.)

Also guide them by recalling and refreshing their memories. They can only hold so much in their head at once. Audio is theater of the mind. Give them a little detail, let it breathe, give them more quotes/details. Repeat stuff you need to repeat to catch the listener back up later (“Remember earlier when so-and-so said X? Well here’s how Sally approached that same problem…”)

Tease using “open loops” — open-ended questions or the beginnings of little stories that you don’t finish until later. A Cold Open is an open loop. A clickbait headline is an abusive open loop, so don’t go that far. 

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Above all, this is about publishing and reflecting, over and over. If you’re doing this right, your early episodes will be your worst, no matter how good you are when you begin. The best way to achieve steady improvement is to treat newly published episodes like an athlete uses game tape: Listen inside the podcast player app you use, with the headphones you use when walking around outside. Consume the episode you made and notice what worked or didn’t.

The only way to improve is to do it, then reflect. The best way to reflect is to consume the thing like a listener would, not like the maker of the show does. If you get stuck, try it a few different ways and supplement it with research and asking around. Don’t start with research and asking around though. You learn to walk by walking. You learn to drive by driving. Google the stuff that’s incremental, but start with what’s fundamental. But to do that, you must start.

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To go deeper with this material, I invite you to listen to 3 Clips, my show about making great shows. Each episode, we try to make sense of an amazing podcast we admire, a few pieces at a time. All links to subscribe and all episodes available at marketingshowrunners.com/podcast