Matt Tillotson
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AI Lesson 4 — Teaching Claude to Remember

Every time you open Claude, you're starting over. No context. Projects fix that.

What is a Project?

A “Project” is a dedicated workspace inside Claude with two key features:

  • Pre-loaded context — instructions, files, and memory you set up once
  • Ongoing conversation history — Claude remembers what you’ve worked on together

Without Projects, every chat is a blank slate. With Projects, you build a tool that gets sharper as you use it.

Projects work best for specialized, recurring tasks.

I created one called Retro Matt Newsletter Content Strategist1 to help with this newsletter.

The three Project components

Every Project includes:

  • Memory
  • Instructions
  • Files

Memory

Memory includes two layers:

  • Project memory (autogenerated as you work)
  • Custom memory: (context you provide)

I uploaded my work history, audience, and content focus.

Instructions

Instructions define how Claude is to behave inside the project. Instructions should be organized by:

  • Role — who Claude is supposed to be (editor, strategist, analyst)
  • Behavior — how it should interact (direct feedback, no cheerleading)
  • Constraints — what to avoid (hustle language, guru positioning)
  • Output Structure — how to format responses

Instructions are fixed. Memory evolves.

For a full instructions example, see my RMNCS2 instructions here.

Files

Files give Claude context inside the Project. I uploaded all of my prior Substack posts to help it discern my writing voice and interests.

Setting up your Project

You’ll find Projects near the top of Claude’s left sidebar.

ai lesson 4 teaching claude to remember 01

  1. Create a new Project and name it
  2. Add Custom Memory — just the facts, Jack
  3. Write Instructions — (role, behavior, constraints, output structure)
  4. Upload Files — reference documents for the project

Once set up, work inside Project instead of the main chat.

ai lesson 4 teaching claude to remember 02

After setup: living documents

Add new files and adjust instructions as you get a feel for what you need. For example, I added an instruction to dial back the lecturing when editing my draft. Claude was telling me why typos are bad, and how they harm credibility. Yeah, I know, Claude. That’s why I want you to fix them …

You’ll want to fine-tune as you go.

Next: Lesson 5 — Context Engineering

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