Skill Retrospective Plan - 2026-04-14

Session Context

Dependabot PR triage session: analyzed 21 open Dependabot PRs, created 4 new PRs (pylint fix, python image bundle, test toolchain bundle, TypeScript 6.0 upgrade), approved 6 low-risk PRs, and created the github:dependabot skill.

Key Session Learnings

What Went Well

The phased approach (discover → categorize → execute) worked cleanly
Bundling saved 8 PRs worth of review overhead (5 python images + 3 test tools)
Catching the TypeScript 6.0 baseUrl deprecation before merge prevented a broken build

Subagent file edits didn't persist — delegated router file edits to a subagent, but changes weren't saved to disk. Had to redo manually. This is a known limitation: subagent writes may not persist in the main session's working tree.
Attempted gh pr merge 3 times before discovering permission block — should have checked permissions first or caught the pattern after the first denial.

Anti-Patterns to Encode

Always verify subagent file writes with git diff before moving on
After a single gh pr merge denial, switch to approve-only and inform user

Proposed Changes

Skills to Update

Skill	Change	Reason	Priority
`github:prs`	Add Troubleshooting section	Missing per audit	Medium
`github:issues`	Add Troubleshooting section	Missing per audit	Medium
`github:my-status`	Add TOC	Over 50 lines, no TOC	Low
`github:last-week`	Add TOC	Over 50 lines, no TOC	Low
`github:streamer`	Add TOC	Over 50 lines, no TOC	Low

Skills to Refactor

Action	Skills	Reason	Priority
Parameterize	All 7 hardcoded github skills	Use `$OWNER/$REPO` variables instead of `rossoctl/rossoctl`	High

This is the single highest-impact improvement. 7 of 9 github skills hardcode rossoctl/rossoctl, making them unusable in other repos. The new github:dependabot skill already uses variables — the others should follow.

Approach: Add a "Variables" section at the top of each skill (matching github:dependabot pattern), then find-replace rossoctl/rossoctl with $OWNER/$REPO in all commands. For skills that reference repo-specific details (like namespace names or file paths), keep those as-is but add a note that they are repo-specific.

New Skills

None proposed — the github:dependabot skill was already created during this session.

Skills to Delete

None.

Estimated Effort

Parameterize 7 skills (bulk find-replace + add Variables section): ~30 min
Add Troubleshooting to 2 skills: ~10 min
Add TOCs to 3 skills: ~5 min

Total: ~45 min of skill maintenance work

Session Context​

Key Session Learnings​

What Went Well​

Blind Paths Taken​

Anti-Patterns to Encode​

Proposed Changes​

Skills to Update​

Skills to Refactor​

New Skills​

Skills to Delete​

Estimated Effort​