17-retrospective

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Reviews Cursor agent conversation logs and pipeline skills 00-16 against project artifacts, then interviews the user with batched AskQuestion prompts to capture what went well, what to improve, and brainstorm process fixes. Ends with an interactive skill-update workshop (proposed patches per SKILL.md, user approves via AskQuestion). Produces a retrospective report and prioritized action backlog. Use after milestones, phase completions, hotfix cycles, evolve cycles, or when the user asks for a retrospective, lessons learned, or pipeline improvement — not for bug fixes (14-hotfix) or feature work (16-evolve).

Math-Data-Justice-Collaborative By Math-Data-Justice-Collaborative schedule Updated 5/24/2026

name: 17-retrospective description: > Reviews Cursor agent conversation logs and pipeline skills 00-16 against project artifacts, then interviews the user with batched AskQuestion prompts to capture what went well, what to improve, and brainstorm process fixes. Ends with an interactive skill-update workshop (proposed patches per SKILL.md, user approves via AskQuestion). Produces a retrospective report and prioritized action backlog. Use after milestones, phase completions, hotfix cycles, evolve cycles, or when the user asks for a retrospective, lessons learned, or pipeline improvement — not for bug fixes (14-hotfix) or feature work (16-evolve).

17 — Retrospective

Meta-improvement stage: mine conversation evidence, compare it to skills 00–16 and workflow artifacts, then run a structured user interview to learn and plan better process — without re-running the pipeline.

Preamble: pipeline-preamble.md — shared conventions for stages 00–17. Sessions: sessions-reference.md — requires active_session unless waived; reports under docs/sessions/{id}/reports/. Cross-cutting: considerations.md, connectivity-gates.md. State agent: workflow-state-manager — mandatory read/update.

When reviewing pipeline gaps, ask whether connectivity tiers (H0c/H0i/H4/H5) were skipped or misunderstood in the session under review.

User is the source of truth. Agent-inferred themes are hypotheses until the user confirms via AskQuestion. Do not edit skills, rules, or product code until Phase 6 — Skill update workshop: each target file gets a concrete proposed patch and its own AskQuestion approval (or defer/waive). Backlog-only items never auto-edit.

When to use

Situation Use
Phase or milestone just finished 17-retrospective
Several hotfixes or evolve cycles completed 17-retrospective
Pipeline felt slow, confusing, or repetitive 17-retrospective
Before changing skills 00–16 org-wide 17-retrospective (evidence first)
Production bug or patch 14-hotfix
New product feature 16-evolve
Scope/API change (no new Fn) 16-evolve
Modal health investigation only 15-service-health

Prerequisites

  1. workflow-state.yaml exists (any stage progress is fine).
  2. At least one of: agent transcripts for this repo, or user can paste/export session links.
  3. User agrees to scope (time window, stages, depth) in Phase 0.

If transcripts are unavailable, proceed on workflow-state.yaml, docs/, git history, and user memory — record the gap in the report.

Interactive questions (required)

Every user-facing question must use the AskQuestion tool. Do not post interview prompts as markdown lists expecting inline replies.

Reference: considerations.md §7.

Situation Pattern
Intake / scope 2–4 questions per batch
Per-stage rating One AskQuestion per stage (or batch 2 stages if user chose "fast")
Themes / brainstorm One AskQuestion per theme; options include concrete skill patches
Action routing One AskQuestion: implement now / backlog / ADR / waive
Skill update workshop One AskQuestion per skill file (or batched pair): apply patch / modify / defer / waive
Skill workshop opener One AskQuestion: which RA items enter the workshop this session
Single gate First option = recommendation; last = Let me explain / provide more context

Privacy and evidence hygiene

Before mining transcripts:

  1. AskQuestion: Include transcripts in scope? (full / date range / exclude current session / none)
  2. Do not paste secrets, tokens, or full API keys into reports — redact if seen.
  3. Prefer summaries (counts, dates, skill names, failure classes) over long verbatim quotes.
  4. Cite sessions as [short title](uuid) per user rules — never cite subagent transcript IDs.

Transcript paths and parsing: reference.md §Conversation logs.

Session management

Per sessions-reference.md §10 and workflow-state-agent-protocol.md.

  1. Agent read_context must return active_session (or blocking deviation).
  2. Current stage must appear in active_session.routing_plan unless user amends plan.
  3. Write stage reports to active_session.artifacts_dir/reports/ when this stage produces a report.
  4. On completion: update routing-plan entry status; mirror project.stages.{key} via agent update.
  5. 00-context exempt from active_session requirement (session opener). Report: reports/retrospective.md.

State management

Agent protocol: workflow-state-agent-protocol.md. Stage key: stages.17-retrospective.

Invoke workflow-state-manager read_context before any other action; update after each substep. Do not edit workflow-state.yaml directly.

retrospective_cycles[]. Rules: workflow-state-reference.md.

Retrospective cycles

Each invocation starts or resumes a retrospective cycle — schema in reference.md §YAML schema.

On invocation:

  1. Read workflow-state.yaml.
  2. If a cycle is in_progress, report position and AskQuestion: resume / abandon / start new.
  3. If none in progress, start Phase 0 — Intake.

After every substep: update the active cycle immediately.

Commit-as-you-go

Commit artifacts to an appropriate branch before transitioning to the next stage or asking the user a blocking question. Branch type per workflow-state-reference.md §Git history. Record every commit in workflow-state.yaml §git_history.commits with stage: "17-retrospective".

Artifacts

Artifact Path
Session report docs/retrospectives/YYYY-MM-DD-{slug}.md
Rolling backlog docs/retrospective-actions.md (append; create if missing)
Skill patch proposals Section in report + optional PR checklist (no auto-edit)

Delta / feature-addition mode

If retrospective follows a feature cycle, mine evolve_cycles[] and feature IDs for evidence. Does not implement features — process improvement only.

Workflow overview

Phase 0 — Intake (scope, depth, transcript consent)
       │
       ▼
Phase 1 — Evidence digest (transcripts + state + docs + git)
       │
       ▼
Phase 2 — Skill rubric pass (00–16 vs evidence, hypotheses only)
       │
       ▼
Phase 3 — User interview (went well / improve / friction)
       │
       ▼
Phase 4 — Brainstorm solutions (AskQuestion-driven)
       │
       ▼
Phase 5 — Action routing (backlog, ADR, skill edit, 16-evolve, waive)
       │
       ▼
Phase 6 — Skill update workshop (propose patches, AskQuestion per file, apply if approved)
       │
       ▼
Phase 7 — Report + state complete

Phase 0 — Intake

AskQuestion (one call, 2–4 questions):

  1. Scope: Full pipeline 00–13 · Maintenance 14–15 only · Evolve/hotfix only · Custom stage list
  2. Time window: All time · Since last retro · Since date · This session only
  3. Depth: Deep (per-stage interview) · Standard · Light (themes only)
  4. Transcript consent: Full · Range · Exclude current · None (artifacts only)

Record answers on the new retrospective_cycles[] entry (scope, time_window, depth).


Phase 1 — Evidence digest

Build an internal Evidence digest (not shown verbatim to user until validated in Phase 3).

Sources (read in parallel where possible)

Source Extract
workflow-state.yaml Stage statuses, dates, issue_log, decisions_log, evolve cycles
docs/execution-plan.md Task churn, blocked tasks, gate log
docs/hotfix-log.md, docs/incidents/ Post-deploy pain
docs/deploy-report.md, service-health reports Ops friction
docs/*-decisions.md, docs/adr/ Decision volume and rework
Agent transcripts User goals, skill invocations, loops, AskQuestion density — reference.md
git log --oneline (scoped) Commit cadence, fix churn

Transcript mining (when consented)

  1. List transcript folders under the project agent-transcripts/ directory (newest first).
  2. Filter by time_window (folder LastWriteTime or first user message date).
  3. For each session, extract per reference.md §Mining checklist.
  4. Map sessions → likely stages (keyword/skill path heuristics; mark confidence low/medium/high).

Digest output shape

## Evidence digest (internal)
- Sessions reviewed: N
- Stages touched (inferred): ...
- Recurring patterns: ...
- issue_log / hotfix themes: ...
- Spec vs code vs tooling (considerations §1): counts by class
- Open questions for user: ...

Update cycle: evidence_digest_path or inline evidence_summary in YAML.


Phase 2 — Skill rubric pass (00–16)

For each stage in scope, read .cursor/skills/{NN}-*/SKILL.md (and pipeline/SKILL.md for orchestration). Score against evidence using the rubric in reference.md §Per-stage rubric.

Produce hypotheses only — table format:

Stage Skill worked? Evidence Hypothesis Confidence
07-build Partially 3 resume loops State pointer unclear medium

Do not ask the user yet; Phase 3 validates hypotheses.


Phase 3 — User interview (went well / improve)

Interview order follows reference.md §Interview order.

Depth: Deep

For each stage in scope, one AskQuestion with 2–3 questions:

  1. What went well for this stage? (options from digest + "Something else")
  2. What should improve? (options = top hypotheses + "None — stage was fine")
  3. Friction rating: Smooth · Some friction · Major pain

Depth: Standard

Batch 2 stages per AskQuestion (same three question types per stage in prompt text).

Depth: Light

Skip per-stage loop; go to Phase 4 cross-cutting themes only.

Cross-cutting batch (all depths)

After per-stage (or instead, for Light), one AskQuestion:

  • Overall pipeline went well (pick up to 3 themes)
  • Overall improve (pick up to 3 themes)
  • Biggest surprise (unexpected rework, cost, or confusion)

Record verbatim user choices in docs/retrospectives/...md §Interview responses.


Phase 4 — Brainstorm solutions

For each improve theme the user confirmed (not merely hypothesized):

  1. Propose 2–4 concrete options (skill text change, new hook, ADR, execution-plan task, run 16-evolve, run 14-hotfix pattern, doc-only).
  2. AskQuestion: Which option(s) to pursue? Multi-select if allow_multiple: true.
  3. Optional second batch: "Combine into one change set?" for related themes.

Brainstorm rules:

  • Prefer small, testable process changes over rewriting entire skills.
  • Reference exact skill file and section when proposing edits.
  • If the fix is product/code, route to 16-evolve or 14-hotfix — do not smuggle code changes into retro.

Phase 5 — Action routing

Consolidate approved ideas into a prioritized table:

ID Action Owner Target Priority
RA-001 Clarify 07-build resume pointer in SKILL.md agent+user .cursor/skills/07-build/SKILL.md P1

AskQuestion (routing gate — not the skill-edit gate; that is Phase 6):

  1. Route skill/rule targets to Phase 6 workshop this session? (All P1+P2 / P1 only / Backlog only)
  2. Create ADR(s) for process decisions? (Yes / No / Later)
  3. Schedule follow-up retro? (After next milestone / After next hotfix / No)

Apply user choices:

  • Backlog only: Append to docs/retrospective-actions.md with status open; skip Phase 6 unless user later opts in via workshop opener.
  • ADR: Create docs/adr/ADR-{NNN}.md per considerations §8.
  • Workshop this session: Mark skill-target RA rows for Phase 6; do not edit files here.
  • 16-evolve / 14-hotfix: Add pointer row in backlog — do not invoke without user ask.

Log actions on the cycle entry (actions[]).


Phase 6 — Skill update workshop (required closing step)

Turn approved brainstorm items into concrete, reviewable skill patches and walk the user through them with AskQuestion — this is the mandatory end-of-review step before the report is finalized.

6.1 Build the workshop queue

From Phase 5 actions[], collect every row whose target is under .cursor/skills/ (including reference.md companions). If the queue is empty:

AskQuestion (single gate):

  1. Any skills 00–16 (or pipeline) to improve from this retro anyway?
    • Yes — I'll name them · No — skip workshop, proceed to report
    • Let me explain / provide more context

If No, record skill_workshop: skipped on the cycle and go to Phase 7.

6.2 Workshop opener

AskQuestion (one call, 2–3 questions):

  1. Which items enter the workshop now? Multi-select from RA rows that touch skills (default: all P1 skill targets pre-selected in options).
  2. Edit scope: Project skills only (.cursor/skills/ in this repo) · Also org-wide template skills (if applicable) · Defer all to backlog
  3. Batching: One question per skill file · Batch up to 2 related skills per question (e.g. 09-qa + 11-verify-impl)

6.3 Propose and confirm each patch

For each skill file in the workshop queue (respect batching choice):

  1. Read the current SKILL.md (and reference.md if the patch belongs there).

  2. Draft a minimal patch: exact section heading, 2–5 bullet summary of change, and a short before/after excerpt (not the full file) in the report draft.

  3. AskQuestion — one call per file (or per batch of 2):

    Question Options (customize per patch)
    Apply this patch to {path}? Apply as proposed (recommended) · Apply with my edits (→ follow-up) · Defer to backlog only · Waive — no change needed
    If companion reference.md also changes Same four options, or "N/A — SKILL only"

    Rules:

    • First option = the agent's recommended patch.
    • Last option = Let me explain / provide more context.
    • If user picks Apply with my edits, ask one follow-up AskQuestion (or accept their free-text in "explain") then revise the patch and re-ask Apply revised patch?
    • Defer / Waive: update the RA row status; do not edit the file.
  4. Apply only after explicit Apply (or Apply revised patch) for that file. Edit the minimum text needed; prefer additive checklists and AskQuestion reminders over rewrites. Update matching reference.md sections when the SKILL points there.

  5. Record on the cycle: skill_patches[] with path, status (applied | deferred | waived), and one-line summary.

6.4 Cross-cutting skill themes

After per-file questions, if multiple patches hit the same theme (e.g. "resume pointer", "AskQuestion batching"), one AskQuestion:

  • Fold into a shared pipeline/SKILL.md or considerations.md edit?
    • Yes — add to pipeline · Yes — add to considerations §… · No — keep per-skill only
    • Let me explain / provide more context

Apply only if user selects a Yes option.

6.5 Workshop close gate

AskQuestion:

  1. Commit skill edits now? (Yes — one commit if user requests · No · Already committed)
  2. Open a PR for skill-only changes? (Yes / No / N/A)
  3. Anything else to patch before the report? (List files / No / Explain)

Do not invoke 16-evolve or change product code in this phase.


Phase 7 — Report and close

Write docs/retrospectives/YYYY-MM-DD-{slug}.md using the template in reference.md §Report template (include §Skill updates).

Update workflow-state.yaml:

  • stages.17-retrospective status / timestamps / last_report
  • Active retrospective_cycles[]: status: completed, completed date, artifact paths, skill_patches[]

Present a short summary to the user: top wins, top improvements, skills updated (applied / deferred / waived counts), open actions count, report path.


Relationship to pipeline skills

Skill Retrospective focus
00–03 Planning clarity, interview length, verify-plan signal-to-noise
04–06 Tech plan ↔ product plan, tooling ROI
07–08 Build throughput, TDD, execution-plan sync, PR cadence
09–11 QA/e2e/impl verification fit
12–13 Deploy gates, smoke value
14–15 Incident response, Modal ops loops
16 Evolve cycle overhead vs value
pipeline Orchestration, gates, state file ergonomics

Legacy skills (doc-planner, build-executor, etc.) are out of scope unless transcripts show they ran.


Exit criteria

  • User completed intake and (per depth) interview batches
  • Phase 6 skill workshop completed (patches applied, or user explicitly skipped)
  • Report written under docs/retrospectives/ (includes skill update outcomes)
  • Actions recorded (backlog and/or ADR and/or applied skill edits)
  • workflow-state.yaml cycle marked completed

Additional resources

  • reference.md — YAML schema, transcript mining, rubric, question banks, report template
Install via CLI
npx skills add https://github.com/Math-Data-Justice-Collaborative/vecinita --skill 17-retrospective
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