Season 1 · Episode 72 · September 30, 2026 · 1h 5m

Has Claude’s Output Got Worse? Here’s What You Can Control | Re-release with Rob Webster

Show Notes

Claude’s output has felt harder to work with recently. It ignores instructions, produces overlong, overwritten answers and can get worse over a long conversation. But if you want to improve your AI output, the answer might just be sitting in your Documents folder.

In this re-released episode, Jess and Kyle speak with Rob Webster, founder of TAU Marketing Solutions, about managing AI context. The tools and product names may be moving fast, but the practical problem has not changed: AI performs better when it has clear, well-managed context.

In this episode, Rob explains how to set up a few plain text files and folders so your AI knows who you are, what you do and what good looks like before you type a word. He also explains why giving your AI everything at once tends to make answers worse, how to spot when your setup has got bloated, and why the same files are the foundation for Claude Code and AI agents.

Follow Rob:

LinkedIn: https://www.linkedin.com/in/marketingaivisionary/
TAU Marketing Solutions: https://taums.ai/

What You'll Learn

Why AI forgets instructions in long conversations, and how better context can improve output
The difference between persistent and situational context
How to organise plain-text and Markdown context files
Why more connected documents do not always produce better AI answers
What to retain permanently and what to remove when a project ends
How to identify context drift early
Why this approach provides a foundation for Claude Code, Claude Cowork and AI agents

Timestamps:

00:43 Introduction and Weekly Updates

03:09 Claude’s Output Has Got Worse, So We’re Revisiting Our Setups

11:12 Markdown Files and the Two Types of AI Context

14:24 Reintroducing Rob Webster

16:31 The Goldfish with a PhD: Why AI Forgets Everything

20:17 What You're Losing Every Time You Open Claude Without Context

26:11 Context Drift: Why AI Outputs Get Worse the More You Use It

29:26 How to Start Giving Your AI Context About Who You Are

35:35 Making It Stick: Naming Chats, Pinning Projects, Starting Your Folders

39:02 What a Working Folder Structure Actually Looks Like

40:38 Where Your Files Should Live