How I got better at doing interviews.

A story of embarrassment and my new system to keep improving.

My first podcast experience was the most embarrassing moment in my life.

I took the MEL19 cohort over to SF and we got onto Jason Calacanis’ This Week in Startups podcast. Bullets of sweat dripping off my face, stuttering my way through - I was thrown right into the deep end on that one.

It was so embarrassing I still can’t rewatch the video and was scarred off podcasts for years.

[watch from 1:03:45 🥵]

But the only way you progress is through going outside your comfort zone and learning from it.

Pain + Reflection = Progress

Step 1 - Lean into the pain

That was enough pain for a lifetime, but the only way to get better was to keep leaning into it.

Practice. Practice. Practice.

I started with the podcasts where I knew the host personally. It helped me to be more natural. I kept practising on dozens of podcasts.

Step 2 - Instant feedback

Even though I still hate listening to my own voice and can’t register to any of my recordings. I had to figure out a way to reflect on the hours and hours of recordings.

The first and easiest way I found is to ask others.

Whenever someone tells me they looooved a podcast I was recently on. Rather than awkwardly saying ‘thank you’ and changing the conversation to something else. I now get excited to see what they remembered, so ask:

“What was your favourite part?”

It is the perfect piece of feedback to understand which stories stayed with the listener. And yes, it is only ever stories or catchphrases that are truly memorable.

It is a massive bonus if you can get an answer to

“What was your least favourite part?”

Write the answers down.
Practice the stories your audience remembers.

Step 3 - Structured reflection

This is the pro step.

For anyone who likes a bit of structure and data, this is the fun part.

I researched a dozen+ tools to transcribe podcasts. They are all expensive and usually made for podcast hosts (understandably so, as they are the power users, I am not). The best one from what I heard is Descript.

Shoutout to Mason Yates for mentioning I could do it on Dovetail.

Dovetail is a customer research analysis solution, so it didn’t naturally come to mind, but does the job brilliantly! (Aussie startup - check them out!)

The process is pretty simple but does take 20-30mins per recording.

1. Get the recording

Either download the recording or ask the host to send you the .mp3 file.

Bonus: also ask if they have the transcript, many hosts have already done the hard work and transcribed it.

2. Upload and transcribe on Dovetail

Upload your audio or video recording and it will automatically transcribe. Even better if you upload the transcription directly.

The free Dovetail tier allows you to transcribe 3h of content every month.

3. Tag your favourite segments

This is where you can be creative and explore all the Dovetail features. I’ve only scratched the surface.

Go through the transcript and tag your favourite parts.

I’ve adopted the below tags to separate what type of snippet it is.

• Quote

• Story (about someone else - ie Startmate alumni)

• My Story (about my life)

• Framework

• Concept (catch-all for everything else)

4. Capture insights

As you’re tagging, capture the “insight”.

In a couple of words, what is the kernel of the message?
What is a memorable title for the story or framework that you’ll recall it from?

If you’ve been on multiple podcasts, you might have covered the same story a couple of times. Use the same tag and insight.

5. Create an Insight Board

For visual learners, this is the great part.

Create your own Insight Board, grouping your quotes and stories into categories that feel intuitive.

This is your Central Home of podcast insights.

7. Revisit and reflect on each insight

Go through each insight and reread what you said.

This can be cringe as you realise how often you say “ehm”, “actually” and “essentially” (ehm, these are what I struggle with 😅). It might even feel awkward as you realise how much-assumed knowledge there is in what you said and how you left out too much context.

Now, is your time to reflect.

At the top of your “insight” rewrite the core pieces of your story, framework, concept or quote. It is your opportunity to improve the narrative. Your opportunity to craft a better story next time you get asked a similar question on a podcast.

Step 4 - Spaced repetition

Finally, just because you reread your recording once, you won’t magically improve overnight.

I recently listened to Andy Matuschak’s episode on the Jolly Swagman, which covered the fundamental learning technique of spaced repetition.

Andy goes into incredible depth about what he coined Zettelkasten.
The core of the technique are Flashcards that you might remember from school.

The idea is to write a prompt on one side of the card for you to remember what’s on the other side ie the full definition or concept. You practice the cards and put the cards you recall easily to one side. The ones you forgot to the other side. And keep practising the ones you keep forgetting until you can easily recall all of them.

But how can you do that virtually?

Luckily, I’ve done the research for you and checked out a dozen+ tools.

The one I landed on is Remnote.

It is free and syncs between your desktop and your phone.

Create the cards easily on your laptop.

Practice the cards on your phone when you’re on the bus or have a free minute. As you practice the cards you swipe in either direction for the system to learn what you’ve already memorised or keep forgetting.

Step 5 - Lean back into the fun :)

…but this time armed with your best stories.

Practice until being outside of your comfort zone is part of your routine and becomes fun!

🔁 Gonna give it a go? Hit me up!

If you have recorded 5+ podcasts and are going to try this method - hit reply and I’ll create a small WhatsApp group!

I’m keen on improving this system, swapping notes and sharing good podcast recommendations.

🎤 Hosting a podcast? I need to get better!

If you are a podcast host, I want to improve - hit me up and I’ll happily come on your podcast to talk about any of the below!

• Startmate, Puddle Pod, startups, the job of a CEO, productivity, getting a job or investing in startups

📽️ Doing video content? I’m a noob and need to lean into the pain!

Finally, my next challenge to really push myself out of my comfort zone is to improve on video, so if that’s you - push me and hit me up!