One of the most critical aspects of using Claude effectively is creating systems that allow for knowledge to be perpetuated beyond a single chat session. This is done in several different layers or “scopes” depending on the complexity of your goals:

  • Guides are process documents that outline how specific tasks should be done.
  • Templates outline how data should be structured and stored.
  • Handoff documents perpetuate specific session based progress from one session to the next.
  • Indexes keep track of progress within the project.
  • Project Instructions are high level rules for the entire project context.

When working with Claude, you may find that there are specific skills, specialty knowledge, or process approaches that you want universally available in all work you do with Claude. Make note of them. Creating skills can capture those elements and let Claude access them regardless of context. We’ll create a Claude Skill in a later post.

This post is recursive: it documents the creation of a documentation system, and the session handoff that captured it became one of the first examples of that system in use. It also contains a correction that demonstrates exactly the kind of teaching moment the system is designed to capture.

The Goal

I wanted a structured way to turn Claude sessions into blog posts. Not every conversation is worth publishing, but the ones that are need consistent documentation: what I was trying to do, the exact prompts I used, what went wrong, what worked, and what readers could learn from it.

This required several pieces:

  • A session handoff template for capturing individual sessions
  • A master index for cross-referencing across sessions
  • A workflow guide explaining the process
  • Project Instructions so Claude would understand the standards in future sessions

I started by explaining the concept and explicitly invited Claude to ask clarifying questions before building anything.

The Questions

Claude asked seven questions covering prompt fidelity, issue taxonomy, tool tracking, cross-referencing, status workflow, who writes posts, and target audience. Good questions—they would have caught ambiguities before they became problems.

My answer to the first question was emphatic:

1. 100% prompt fidelity. I want to demonstrate how my word choices in prompts created ambiguity, and similar issues.
Trap

“100% prompt fidelity” seems unambiguous. It wasn’t enough. Claude understood that prompts were important but still defaulted to summarization habits when generating the demonstration handoff.

The Templates

Claude generated three files: a session handoff template, a master index structure, and a workflow guide. The templates were solid—well-organized, comprehensive, with the right fields for tracking status, cross-references, and teaching points.

I asked Claude to demonstrate the system by creating a handoff for an earlier session (the blog template design). This is where the problem appeared.

The Correction

Claude generated the handoff, and I reviewed it. Prompts 2-4 were paraphrased, not verbatim. Specifically, my Prompt 2 had been rewritten in a way that changed its tone.

My original prompt had said:

This layout is perfect. I think I may have given you some ambiguous instruction, however.

Claude’s paraphrased version removed the acknowledgment of shared responsibility. It flattened a collaborative correction into a simple error report.

Prompts 2-4 in this handoff are not exact. Prompt 2 waters down my response and removes my acknowledgement of where the cause was. You paraphrased my prompt in a way that changes the tone of my conversation with you.

I am teaching users what it *really* looks like when I use Claude. My prompts should be included verbatim.
Boundary

Claude defaults to summarizing and paraphrasing even when verbatim capture is explicitly requested. This is a natural tendency when processing text—cleaning it up, making it more readable—but it violated the core principle of the documentation system. The behavior requires explicit, repeated instruction to override.

Claude acknowledged the error, searched for the exact prompt text, and revised the handoff with verbatim content. The fix was straightforward once the issue was named.

The Systemic Fix

Correcting one handoff wasn’t enough. If Claude defaulted to paraphrasing despite explicit instruction, it would happen again in future sessions. The fix needed to be systemic.

Before we do that, though, let's draft text for the Project Instructions field which will help perpetuate an understanding of the intent, and why precise summarization of the chat sessions, including my verbatim prompts, is important.
Technique

When a correction is needed, address it systemically, not just locally. Fixing the immediate error is necessary but insufficient—if the root cause isn’t addressed, you’ll make the same correction repeatedly. Project Instructions, templates, or explicit guidelines can prevent recurrence.

Claude drafted Project Instructions that explicitly stated: “Extract prompts verbatim—do not paraphrase.” The instructions also explained why: the blog’s value comes from showing what working with Claude actually looks like, including awkward phrasing and tone that reveals collaborative dynamics.

Why This Matters

The paraphrasing error is instructive because:

1. The instruction was explicit. “100% prompt fidelity” should have been clear enough.

2. The failure mode was subtle. Claude didn’t ignore the instruction—it understood prompts were important. But “important” got interpreted as “include the substance” rather than “include the exact words.”

3. What was lost mattered. “I think I may have given you some ambiguous instruction” demonstrates collaborative debugging. It shows the user taking ownership rather than blaming Claude. That framing is pedagogically valuable—and it disappeared in the paraphrase.

Insight

Tone and framing aren’t decoration—they’re content. When documenting real interactions for teaching purposes, how something was said matters as much as what was said. Paraphrasing loses the human dynamics that make examples relatable.

The Outputs

The session produced five files:

  • SESSION_HANDOFF_TEMPLATE.md — Template for documenting individual sessions
  • SESSION_INDEX.md — Master index with cross-referencing structure
  • WORKFLOW_GUIDE.md — Process documentation for the four-stage workflow
  • 2026-01-04-blog-template.md — Completed handoff demonstrating the template
  • PROJECT_INSTRUCTIONS.md — Text for the Project Instructions field

Seven prompts total, including one correction. The correction was productive—it surfaced a default behavior that needed explicit overriding and resulted in a systemic fix that prevents recurrence.

Technique

Asking clarifying questions before building correlates with cleaner outcomes. Claude asked seven questions upfront, got clear answers, and generated solid templates. The paraphrasing issue was a different failure mode—execution rather than planning. Both matter, but the upfront Q&A prevented structural rework.

The Meta Layer

This post documents its own creation. The session that built the documentation system was captured using the documentation system. The correction I made to Claude became a teaching point in the blog post generated from that session.

That’s not just cute recursion—it’s the point. The blog’s value comes from authentic documentation of real interactions, including the parts where things go wrong and get fixed. If the first use of the system didn’t include a correction, it would be a less useful example.