Three Rounds of Not Quite Built the Skill I Needed

How a fuzzy idea about teaching through AI conversations became a working /teaching-block command — and what each failed version revealed.

Step 1 — Naming What I Actually Wanted

The origin problem: productive Claude sessions leaving nothing shareable. I wanted a skill that reads the conversation and produces a walkthrough article. After sitting with that for a while, I landed on four constraints: process walkthrough, capture reasoning, include actual artifacts, reader can follow the process themselves.

Concept #1: Describe outputs by the reader’s experience, not the document’s structure.

Step 2 — The First Spec: Well-Written, But Wrong

I invoked /anthropic-skills:skill-creator. The first spec leaned into narrative — “discovery memoir,” “narrative arc.” The eval outputs were well-written but felt like stories about a process rather than ones that transfer it. Reading them, you understood what I went through. You couldn’t do it yourself.

That’s the gap. Engaging is not the same as useful.

Concept #2: Don’t conflate engaging with useful.

Step 3 — Borrowing Structure from a Gold Standard

I added the Experienced Insight Guide voice style and referenced a gold-standard article. A subagent extracted a 4-beat section formula from the reference:

Wrong path — what I tried that didn’t work
Right path — what actually worked
Generalization — the underlying principle
Action — what the reader should do

I rewrote the spec to require wrong-path-first structure and numbered concept stamps. The outputs shifted. They stopped being memoirs and started being walkthroughs.

Concept #3: Steal structure, not just voice.

Step 4 — Show-and-Tell, But the Wrong Person Was Talking

Feedback named the “show-and-tell” reframe. The spec was still telling the reader what I tried rather than showing the actual artifact. I changed the spec language:

Before:

“Describe what was tried at each step.”

After:

“Quote it verbatim when useful. Show the artifact, then explain it.”

The difference: when the spec said “describe,” the output described. When it said “quote verbatim,” the output showed. Small language change, large output change.

Concept #4: Show the artifact, then explain it. Don’t describe what the reader could see.

Step 5 — “How I Did It” vs “How To Do It”

Even after Step 4, outputs were drifting into tutorial voice: “First, do X. Then, do Y.” That’s not wrong exactly — but it’s not the genre. Teaching-block is a first-person account of a process, not a recipe.

Fix: I added a first-person past tense constraint throughout the body and explicitly banned tutorial voice patterns. “I tried,” “I found,” “it turned out” — not “try,” “you’ll find,” “it turns out.”

Concept #5: Treat first-person past tense as structural, not stylistic.

What This Unlocks

The pattern generalizes beyond skill-building. Any session with a clear process — client discovery, research, debugging, strategy — is a candidate. The requirement is that you made decisions with reasons, and those decisions produced visible artifacts. If both are true, a /teaching-block run can produce something a reader can follow.

Candidate session types:

Client discovery with a real output (diagnosis, recommendation, proposal)
Research sessions where the search strategy itself is interesting
Debugging sessions where the wrong paths are as instructive as the right one
Strategy sessions where the reframe is the content

Key Takeaways

Name the output by the reader’s experience, not the document’s structure
Engaging and useful are different things — calibrate toward useful
Borrow structural scaffolding from work you already admire; voice alone isn’t enough
Show artifacts verbatim; then explain them — don’t describe what the reader could read themselves
First-person past tense is structural in teaching content, not just stylistic preference

How to Start

Find a session where you made at least three decisions with visible reasons
Invoke /teaching-block at the end of that session or after reviewing the transcript
Check the output against the five concepts above — each one is a pass/fail gate
If a section reads like a tutorial (“First, do X”), rewrite it as what actually happened (“I tried X because…”)
If a section describes an artifact rather than showing it, paste the artifact in and trim the description

— Lou / AIMM, April 2026