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Ai Coaching Newsletter

The Evaluation Loop: How AI Improves Its Own Output

Published 21 days ago • 2 min read

⚖️ “With a leveraged worker, judgment is far more important than how much time they put in or how hard they work.” - Naval

Hello Reader,

AI is better at evaluating content than generating content.​
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This makes sense, when you stop to think about it. For a large language model to interpret your instructions, and create output, all in the same step, it dilutes the same token budget over two requests.
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But if you have ask AI to evaluate its own outputs, it can focus all its attention on identifying how to improve. Then it can rewrite, separately.
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Here’s a simple copy/paste process you can use to rapidly improve your LLM responses:

  1. Ask an LLM to create some content for you
  2. In a second tab, have another LLM evaluate the output.
  3. Ask the second LLM for a clear brief documenting improvements.
  4. Copy that brief, and paste it into the first LLM tab with the prefix, “Analyse this feedback.”
  5. Ask for a V2.
  6. Repeat until satisfied
  7. Compare with diffchecker.com if you want to see the changes

This simple process will help you stir your prompt around in a cauldron, like the wizard of the future that you are.

🎥 Replay: Create a Coaching Relationship with AI

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If you missed my webinar last week, you can watch the replay, and use 30 copy/paste prompts to deepen your relationship with an AI thinking partner.

📰 New AI News This Week

  • Anthropic released Claude Sonnet 4.6 which gives Opus-like reasoning for a fraction of the cost
  • Google launched Gemini 3.1 Pro which has twice the reasoning capacity of Gemini 3
  • Digital Ocean reports the biggest blocker in implementing AI agents in enterprise is the cost of inference

👓 What I’m Reading

📢 Feedback Time!

Are you ready to grow your Ai capabilities?

Join me in the Ai Coaching Academy:

[REPLAY] Create a Coaching Relationship with AI

[REPLAY] Create a Coaching Relationship with AI

Last week's webinar provided 30 copy/paste prompts you can use to deepen your relationship to your LLM thinking partner. Slides https://ai-coaching-academy.s3-ap-southeast-2.amazonaws.com/slides/2026/aica-0226.pdf Copy/Paste Prompts Author In The Machine Speak in the voice of the author from this PDF. Ask me questions based on their ideas. You a...

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- Caelan Huntress

​[email protected]​

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Ai Coaching Newsletter

by Caelan Huntress

Weekly newsletter highlighting the latest Ai news, with 2-minute video tutorials and copy/paste prompts you can use to improve your skills as an Ai operator. Ai is changing all jobs this decade. You are either getting ready to change how you work, or getting ready to retire. As artificial intelligence moves from optional to operational, technical specialists no longer have the advantage. It is those who can supervise and coach Ai to improve that will thrive in an Ai-augmented future.

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