I’ve Transcribed 300+ Coaching Sessions With AI This Year For Notes, And Never Asked The Two Questions That Changed Everything
Strap in Gang, This is a Journey
I’ve been recording and transcribing every coaching session for months, using AI to create summaries and action items for my clients
I discovered MacWhisper about six months ago and it changed my coaching workflow overnight.
See, I record every coaching session. Always have. Zoom’s transcription takes forever, and tools like Fathom feel intrusive in the call itself. MacWhisper gives me an almost instant transcript the moment the session ends.
The reason I started doing this was simple: I’m a senior coach at Blackbelt, working with Taki Moore’s business coaching clients. My fellow coaches need to know what’s happening with each client. I need a record for myself. And honestly, my own note-taking during calls was terrible - I’d either miss half the conversation while scribbling, or I’d send rambling voice memos to my VA to transcribe later.
So I built a system.
Session ends. MacWhisper transcribes it. I feed the transcript to Claude with a prompt I’ve refined over months. Out comes a summary that includes:
What we discussed
Trainings assigned
Blackbelt concepts we covered (things like “right next thing,” the triangle model, the five ones)
Action items for the client
I don’t send these to my own coaching clients - many of them are already using their own AI tools anyway, and they’ve always got the recording if they need it. For me and the Blackbelt coaching team though? Game changer.
Are they perfect? No. I almost always tweak them. Getting that 80% done automatically is so much better than starting from scratch. And in the very near future, this will all be automated with an agentic workflow.
Here’s what I didn’t realize: I was using AI brilliantly for admin, and completely missing the bigger opportunity.
My partner AnnMarie listened to a few calls and said “these all sound really similar” - which got me thinking about patterns I couldn’t see
I’m up in Queensland now, and one of the unexpected benefits is that I can do my morning coaching calls outside. In Melbourne, I’d die of exposure trying that. Here, I sit outside with my headphones on, talking to Blackbelt clients while the sun comes up.
AnnMarie’s usually doing her own work or walking past, and she overhears my side of these conversations.
One morning she mentioned casually: “You know, these calls all sound really similar.”
I was immediately curious. Not defensive - just intrigued.
I probably would have guessed that if someone asked me directly, though I’d never actually thought about it. The more I sat with her observation, the more questions emerged.
What patterns was she hearing that I couldn’t see from inside the conversations?
Here’s the thing about AnnMarie - she’s way further along the inner work path than I am. Over the last couple of years, I’ve been diving deep into this work myself. And one principle I’ve come to believe (and yes, it’s an experiment, a lens I choose to use): if I’m saying something repeatedly, I should get really curious about what that might be revealing.
Not just for my clients.
For me.
If these coaching sessions all sound similar, what am I teaching over and over? And more importantly - why? What’s the universe showing me through these repeated conversations?
That curiosity sat with me for weeks.
I was going through the Blackbelt launchpad myself (practicing what I preach) and realized I needed article ideas for my newsletter
Some events over the past couple of months made it crystal clear: it was time to get serious about building my own business.
Time to get back to the Little Blue Report newsletter. Time to focus on my AI30DC YouTube channel. Time to stop just coaching others through their launches and actually do my own.
The Blackbelt launchpad is all about understanding your market and building your program model - the foundational building blocks of a coaching business. I’ve guided dozens of coaches through this process. I’ve watched Taki and other Blackbelt members build successful businesses, many with smaller YouTube audiences than I have.
Twenty years ago, I was big time. Then I made and lost a couple of fortunes and thought I’d retired. This AI revolution though - like the Mafia - has dragged me back in. Now it’s time to fix the leaky taps.
AnnMarie’s observation about my repetitive coaching conversations gave me the first insight: if I’m saying the same things over and over in client sessions, maybe I should take a leaf out of my own book. Maybe those repeated patterns ARE my market. Maybe that’s what I should be writing about.
I wrote about this realization in last week’s newsletter - a cool little validation of the experiment: if the universe keeps showing you something repeatedly, pay attention.
I’d set myself a goal: four weeks in a row of newsletters. You’re reading number four right now. And I want to make money from this. These Hello Kitty collectables won’t pay for themselves.
I needed article ideas though. Real ones. Not generic “here’s what AI can do” content. Ideas rooted in my actual expertise.
That’s when I thought about the transcripts.
I uploaded four client session transcripts to Claude and asked it to find themes for potential articles
Actually, it wasn’t on a whim at all.
I’d been reading Nicolas Cole’s “Write with AI” newsletter, and he’d just published an article about using AI as a brainstorming partner to generate content ideas. The process was brilliant: you tell Claude what you worked on recently, it drills down with “why” and “how” questions, extracts insights, and helps you see what’s worth writing about.
The whole article was about jamming on what you’d experienced - turning your daily work into educational content.
If you want to use this exact process yourself, I highly recommend subscribing to Nicolas Cole’s Write with AI newsletter - he provides the complete prompts and Claude Project setup that I used.
I’d been seeing these clear signs pointing me in the right direction. AnnMarie’s comment about my calls sounding similar. Going through the launchpad myself. Needing article ideas for four consecutive weeks of newsletters.
So I thought: what if I just gave Claude my actual session transcripts instead of talking about what happened?
I had four coaching calls scheduled yesterday - velocity calls with Blackbelt members. All recorded. All transcribed with MacWhisper.
No cherry-picking. Just the four sessions from yesterday.
I used Nicolas Cole’s exact prompts and project setup. Instead of typing out “Recently I’ve...”, I uploaded the four transcripts and said: “Here are the key conversations I had yesterday. Let’s start here.”
I was excited. The signs had been pointing this direction. If every interaction is for my benefit, then these transcripts should reveal something.
That’s when gold was struck.
Within minutes, AI identified eight distinct patterns I teach repeatedly - frameworks about audience targeting, simplification, marketing to frustrations - things I didn’t realize I was saying the same way every time
I thought it was freaking cool.
Claude came back with eight distinct patterns from those four calls:
The “Five Ones” concept (one market, one product, one traffic method, one conversion process)
Marketing to frustrations vs. fears
Working backwards from conversion events
Staging promises and outcomes (showing momentum, not promising the end result in 60 days)
Training redundancy (why training just one person is dangerous)
Unifying multiple programs into one sales process
The right audience problem (daily content needs to attract the right people)
Podcasts as lead magnets (terrible for direct response, great as private mini-series)
Now, these aren’t MY frameworks. They’re Blackbelt frameworks. Concepts we reference from other creators. Things I teach coaches every day.
Here’s what made me thrilled though: the way I teach them, the examples I use, the context I provide in real coaching situations - THAT creates unique content.
And any one of the people I coach - or anyone reading this newsletter - could use this exact same process to build a unique, bingeable body of work. Which is vital in this day and age.
You don’t need to invent new frameworks. You need to extract how YOU teach existing ones.
Numbers seven and two hit hardest - the right audience problem and marketing to frustrations. Those were the ones I really needed to double down on. The others were all relevant and in progress in some way, shape, or form.
As you can see from the start of this very session, we began fleshing out the podcast concept. I do love a good podcast, after all. It would have been an awesome article.
Then Claude asked me a question during our brainstorming that prompted a discussion about my views on every interaction being for my benefit. Claude got quite excited. So did I.
And we pivoted to this.
That’s when it hit me: I’m the plumber with leaky taps, using AI for admin but never for strategy
I’m looking at those eight patterns Claude extracted, and then Claude mentions something about using AI for admin tasks - summaries, notes, action items.
That’s when it hit me.
I’d been transcribing hundreds of coaching sessions. Using AI brilliantly for admin. Getting those 80% done summaries that made my life easier.
I could be using the exact same transcripts to create really unique content AND reflect back opportunities for my own insight and growth though.
I’m the plumber with leaky taps.
This was such an awesome moment that I have to pack right now to go to Palm Springs to work with our million-dollar-plus Boardroom members and I can’t tear myself away from what we’re uncovering here.
I see a lot of coaches using AI for admin and that’s cool. What if, for very little extra effort, you could use it for strategy as well?
“Writing is thinking.” (I believe that’s a quote, though I can’t recall who said it first.)
Every person who coaches and works with clients in any context - even in teams and work environments - is sitting on a treasure trove of strategic content.
It’s damn cool.
The two questions that changed everything: “What content patterns exist across my sessions?” and “What are these sessions telling ME about my own journey?”
Here are the two questions that transformed how I think about my coaching transcripts:
Question 1: What content patterns exist across my sessions?
This is the practical one. The content creation engine. You’re looking for the frameworks you teach, the problems you solve repeatedly, the language you use naturally.
I’m using this exact process for the article you’re reading right now. Upload transcripts to Claude in a dedicated Project (with custom instructions and the prompts I’ll share at the end), and let it extract the patterns.
This creates a bingeable body of work that’s authentic because it comes from your actual expertise in action, not from staring at a blank page wondering what to write.
Question 2: What are these sessions telling ME about my own journey?
This is the one that might sound strange if you haven’t explored inner work.
Here’s what I’ve come to believe after three years of pretty intense inner work: every interaction you have is showing you something about yourself. Not in some mystical way - think of it like this: your clients’ challenges often reflect challenges you’re working through yourself. The problems you’re most passionate about solving for others are often the ones you most need to solve for yourself.
With my physics background, it makes sense. Everything is waves and photons interpreted by your brain. What we perceive “out there” is an interpretation created by our consciousness.
You don’t have to believe any of that though.
Just try it as an experiment: What are the common elements across your coaching sessions that might be relevant to YOUR journey right now?
You might be surprised. I used to be surprised. Now I just accept it. It makes sessions more fun and it’s an interesting way to look at life.
This is one of the most practical benefits and observations from years of inner work.
And here’s the thing - I started this whole process as an opportunity to mine content for my newsletter. It became something more through working with AI. Which is exactly the point: using AI for both the practical AND the strategic.
The first question is practical - extract your expertise, find your frameworks, never run out of authentic content ideas again
Here’s the workflow: Record session. Transcribe it. (I use MacWhisper because it’s local on my computer and very fast, though any transcription tool works.) Upload to a Claude Project with custom instructions. Ask for patterns.
How often? Match it to your publishing schedule. The Little Blue Report is once a week, so I had a four-session day and just used that. It would be interesting to ask for themes over a month or even a week - more sessions would reveal even more patterns.
Now here’s the awesome part: this content is all my own thinking and words, cleaned up. It’s the opposite of AI “slop.”
There’s no way you could “one-shot” an article of this caliber. I’ve probably spent two to three CFTs (Critical Focus Time - 50-minute blocks) on this process. Compared to my vomit draft approach - which I’ve been doing for twenty years - this has extracted much more interesting content and ideas. The overall time investment will be similar, and the enjoyment of the process is 10x better.
And as you can tell from this article, it’s me. It’s my voice. I wrote most of it. Just fewer typos.
This isn’t a speed process. It’s a strategic thinking process. There’s room for both - I still do 10-minute freewriting to warm up.
The strategic partnership with AI though? That’s where the magic happens.
I think all types of content could be generated from here. Newsletter articles like this one. Social posts. Course content. Lead magnets. I’m excited to apply this process to my YouTube videos, and I’m starting daily Instagram content soon - something I’m not looking forward to. I’ll be leaning heavily into AI-generated work, instead of generic stuff though, it’ll be based on strategic thinking using a variation of this prompt and project style.
I’m constantly working with coaches who don’t know what to write about. If I got this many interesting ideas from four sessions, and you’re mining what you do on a daily basis plus sessions and conversations with your market - how are you going to run out of ideas?
And when the creation process is this fun? That removes a major barrier.
I’ve done this over multiple sessions, in different continents, and I couldn’t wait to get back to writing to see what else would pop. That’s unusual. And pretty awesome.
Do you need to do this with every session? I don’t think so. I started with four and that was more than enough to produce all these ideas. Three would be a minimum - part of the fun is seeing what’s common across disparate sessions.
The second question is the one I’ve been experimenting with through my inner work: what if every coaching session is also a mirror showing you what you need to work on?
This is where it gets awesome and a little freaky, and I really encourage you to have an open mind and look at this as an interesting experiment.
For now, you could do what I did - just upload some sessions and see what happens.
If I were designing a dedicated process for this though, I’d create it as a separate Claude Project with specific context. Who you are. What you do for work. Who you coach (newsflash: that’s a big tell). What you’re working on. Any influences from coaching and inner work. Goals, plans, projects - anything that will help the AI look for patterns that are relevant to YOU.
I don’t think we need to feed it a particular inner work framework. LLMs work on patterns and probability. Let’s lean into that and let it come up with what it observes as patterns in the context of your coaching sessions.
Use an LLM with a large context window. (A context window is how much information an AI can “remember” and process at once - think of it like working memory. Claude has a 200,000 token context window, which means it can analyze multiple lengthy transcripts simultaneously and spot patterns across all of them.)
Here’s the prompt I’d suggest:
“I’m trying an interesting experiment exploring a theory that in each session I conduct, there’s something of benefit to me. Here are X sessions from the last Y days. Can you look for interesting patterns that may be reflected in these sessions - in particular recurring themes - that could be the basis for me expanding my business and inner work?”
Then add the transcripts and see what pops for you.
For me, the content creation and simplification patterns really were mirrors being held up. Which led to this whole process. Which is awesome.
Why This Makes You A Better Coach
This makes me a better coach in a couple of key ways: My interest in sessions is significantly increased. I’m open and focused on the client, curious to see what in this session is a reflection for me to ponder.
It’s natural in coaching to deal with similar issues repeatedly - that’s part of the game.
Here’s the REALLY interesting thing, and this is where the gold lives:
Pay attention to the ones you react negatively to. The ones where you feel frustration, irritation, that edge of judgment.
“What’s so hard about getting coaches to do five pieces of content? Sheesh!”
I would say this. A lot.
Horrifyingly (initially), these were exactly the things I really should have brought my attention to.
Ed, meet mirror.
The plumber with leaky taps wasn’t just about content extraction. It was about everything I was coaching others to do that I wasn’t doing myself.
This is a really interesting project, and one I’ll be developing further.
Conclusion: The Plumber Is Starting To Fix His Own Damn Taps
So here’s what I learned from uploading four coaching transcripts:
I was using AI brilliantly for admin, competently for summaries, and not at all for the strategic thinking that actually matters.
The two questions that changed everything:
What content patterns exist across my sessions? (The practical engine - never run out of authentic content ideas)
What are these sessions telling ME about my own journey? (The experiment - what if every interaction is showing you something?)
You don’t need to believe the second question to benefit from the first one. I encourage you to try both as experiments though.
Start with three or four recent coaching sessions. Transcribe them. Upload them to Claude in a Project. Use the prompts I’ve outlined here. See what patterns emerge.
You might discover you’re sitting on a year’s worth of newsletter content. You might discover you’re teaching frameworks you didn’t realize you’d systematized. You might discover you’re the plumber with leaky taps in ways you never expected.
I’m still developing this process. The personal patterns piece is going to be its own project, its own set of prompts, its own daily practice.
For now though, I’m excited about what’s possible.
And those Hello Kitty collectables are one step closer to being paid for.
Your Turn:
Try this process with your own coaching sessions or client conversations. Then come back and tell me:
What patterns did you discover?
What surprised you?
What are you going to create from it?
Drop a comment here on Substack or reply to this email. I read every single one, and I’m genuinely curious what you’ll find when you hold up the mirror.
The plumber’s taps are finally getting attention. How about yours?
P.S. Here’s the whole wild session on Claude - it’s long and maybe only interesting to me. However, you can see what I wrote and how Claude assisted, and in the process, has changed the way I write forever.
Hi Ed Might be just me - but couldnt open the Claude session. thanks
https://claude.ai/share/b0b46fb4-7726-418a-bf93-887f1ee1bbbe