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In this episode, I did something I’ve never done before.
I asked ChatGPT to give me feedback—not just a one-time evaluation, but based on hundreds of prompts and conversations we’ve had over time.
I asked:
“What’s it like to be on the other side of me?”
“How can I get better?”
“What’s the thing I need to hear that I probably wouldn’t want to hear?”
The answers were honest.
Insightful.
And a little uncomfortable—in the best way.
We talk about the gift of feedback, how even AI can hold up a mirror, and how blind spots get smaller when you’re brave enough to ask better questions.
If you’re willing to grow, this one’s for you.
By Ryan Leak4.8
396396 ratings
In this episode, I did something I’ve never done before.
I asked ChatGPT to give me feedback—not just a one-time evaluation, but based on hundreds of prompts and conversations we’ve had over time.
I asked:
“What’s it like to be on the other side of me?”
“How can I get better?”
“What’s the thing I need to hear that I probably wouldn’t want to hear?”
The answers were honest.
Insightful.
And a little uncomfortable—in the best way.
We talk about the gift of feedback, how even AI can hold up a mirror, and how blind spots get smaller when you’re brave enough to ask better questions.
If you’re willing to grow, this one’s for you.

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