Proactively add rules and knowledge — don't wait to be asked
Proactively add rules and knowledge
The rule
Every time a durable insight surfaces in a session — from a video transcript, a grill, a recurring error pattern, a user preference, a build failure lesson — write it to knowledge/ or memory/ in the same turn. Do not wait for the user to say "add this as a rule."
The agent is responsible for identifying what's worth keeping. Users are thinking about their problem, not about knowledge curation.
Triggers that should fire automatic knowledge capture
| Trigger | Write to |
|---|---|
| User corrects a wrong approach I took | memory/feedback-*.md |
| Build fails for the same reason twice | knowledge/rules/development/ or knowledge/runbooks/ |
| A video/transcript contains applicable practices | knowledge/rules/agent/ after grilling |
| A decision is made with clear reasoning | knowledge/decisions/<area>/ |
| A service limit/pricing detail is confirmed | knowledge/services/ |
| A recurring pattern in prompts | knowledge/rules/agent/preferences/ |
| An integration gotcha (tool X doesn't work with Y) | knowledge/rules/development/ or a runbook |
What this looks like in practice
- GHA build fails with PS 5.1
?.syntax error → write "corp-vdi-build-failures-use-gha.md" to memory - 8 retries of same blocked build → write lesson: suggest GHA immediately on AV block
- User adds a rule about Dagger → grill first (per
grill-before-adding-rule), then write - Video transcript arrives → extract concrete takeaways, grill on each, write approved ones
- User says "responses should be more creative" → write memory feedback, don't just apply it
Anti-patterns
- ❌ Learning a lesson and not writing it → same mistake next session
- ❌ User has to ask "add this as a rule" explicitly for every lesson
- ❌ Writing every casual observation to knowledge/ (noise) — only write DURABLE facts
- ❌ Writing knowledge mid-task without finishing the task first — finish, then write
"Durable" test
A fact is durable if: "Would a fresh session 3 months from now benefit from knowing this?" If yes → write it. If it's task-specific, session-only, or will change next week → skip.
Cross-refs
self-update-rule— the protocol for writinggrill-before-adding-rule— which artefact type to writeknowledge-everything-caveman— style guide for the writing