session-retrospective

name	session-retrospective
description	Analyzes the current implementation run — evaluates schema effectiveness, delegation alignment, note quality, and plan-to-execution fit. Captures cross-session trends and proposes improvements when patterns repeat. Use after implementation runs, or when user says 'retrospective', 'session review', 'what did we learn', 'analyze this run', 'how did that go', 'evaluate our process', 'wrap up', 'end of session review'. Also use when the output style's retrospective nudge fires after complete_tree.
argument-hint	[optional: root item UUID] [--dry-run to preview without creating items]

Session Retrospective

Structured post-implementation analysis. Evaluates the current run across five dimensions, persists findings in MCP, and maintains cross-session trend memory to surface actionable improvement proposals.

---

Step 0 — Mode Check

If $ARGUMENTS contains --dry-run, set DRY_RUN = true. In dry-run mode, perform steps 1-4 and render the report (step 9) but skip steps 5-8 (no MCP item creation, no memory updates). Announce at the top of the report: **Dry run** — no items created, no memory updated.

---

Step 1 — Gather Scope

Determine which items to analyze by collecting distributed session-tracking notes.

1a. Identify items in scope

If $ARGUMENTS contains a UUID (root item ID):

query_items(operation="overview", itemId="<root-uuid>")

This returns the root item and its children. Collect all item UUIDs from the overview.

A supplied root UUID is the authoritative scope — this covers dispatched mode, e.g. a background agent invoked with the root item ID (see the output style's hook-driven Retrospective dispatch, or the retro-trigger hook's background-agent directive). When a root UUID is supplied, run only this overview call and do not run the fallback scan below (neither the get_context calls nor the terminal-items search) — the fallback scan applies only when no UUID argument was provided.

If no root item ID provided:

Check for a known project root: session context injected by the SessionStart hook, or a project.rootId entry in .taskorchestrator/config.yaml.

If a project rootId is known, scope both fallback calls to that subtree so concurrent runs in other projects sharing the same DB aren't conflated into this retrospective:

get_context(ancestorId="<rootId>") — active, blocked, stalled items within the project subtree
query_items(operation="search", role="terminal", sortBy="modifiedAt", sortOrder="desc", limit=20, ancestorId="<rootId>")

If no project rootId is configured, fall back to the prior global behavior (unchanged):

get_context() — active, blocked, stalled items
query_items(operation="search", role="terminal", sortBy="modifiedAt", sortOrder="desc", limit=20)

Build scope from recently completed items (compare modifiedAt to current date). Discard items that appear stale (modified more than 24 hours ago).

1b. Collect distributed notes

For each item in scope (up to 20):

query_notes(operation="list", itemId="<uuid>", includeBody=true)

operation is required — query_notes has no default and rejects the call without it (Missing required parameter: operation). Use operation="list" to enumerate an item's notes.

Extract:

• Notes with key session-tracking — these contain per-item outcome, files changed, deviations, friction, observations, and test results
• Notes with key delegation-metadata (optional) — orchestrator-recorded model and isolation data

1c. Early exit

If no items are found in scope, or no session-tracking notes exist on any item: Exit early with:

No implementation run data found. Nothing to retrospect — run `/implement` first, then try again.

---

Step 2 — Aggregate Note Data

From the collected session-tracking notes, aggregate across all items:

• Total item count and outcome distribution (success, partial, failed, skipped)
• Combined files list — all files changed across items, deduplicated
• Combined friction list — all friction entries from all items
• Combined observations — notable observations from all items
• Test results summary — pass/fail counts across items

If delegation-metadata notes exist on any items, extract:

• Model used per delegation (haiku, sonnet, opus)
• Isolation mode (inline, worktree)
• These feed into delegation alignment analysis (step 3b)

Run get_context() in parallel for the current state snapshot.

---

Step 3 — Evaluate Across Dimensions

3a. Schema Effectiveness

For each item in scope, examine its actual notes (from step 1b):

• Which schema-required notes exist? Check for non-empty content.
• Token count per note: <50 = sparse (flag), 50-500 = appropriate, >500 = potentially verbose (flag for status-type notes; specification notes are exempt from the upper bound)
• Were any items missing required notes (indicating gate failures or schema-free items)?
• Score: Fraction of expected schema notes that exist with appropriately sized content

3b. Delegation Alignment

If delegation-metadata notes exist on items, cross-reference against the delegation table:

Task type	Expected model
MCP bulk ops, materialization, simple queries	haiku
Code reading, implementation, test writing	sonnet
Architecture, complex tradeoffs, multi-file synthesis	opus

• Flag misalignments (e.g., opus for bulk MCP ops, haiku for architecture)
• Score: Fraction of delegations matching expected model for their task type

If no delegation-metadata notes exist: Note "delegation metadata not recorded" and skip scoring for this dimension.

3c. Note Effectiveness

For items with both queue-phase notes (specs) and work-phase notes (implementation):

• Compare spec content themes to implementation note themes
• If implementation notes mention "deviated from spec", "unexpected", or "assumption was wrong" -> flag as a spec gap
• If work-phase notes are nearly empty (<30 tokens) -> flag as context loss for downstream agents
• Score: Qualitative (effective / mixed / ineffective)

3d. Plan-to-Execution Alignment

Compare item creation timestamps to the root item's creation time (or the earliest item in scope if no root provided):

• Items created significantly after the root (>1 hour) = ad-hoc additions (may be necessary or scope creep)
• Items still in queue role under the root = planned but skipped
• Score: Fraction of planned items that reached terminal

3e. Friction Synthesis

Extract friction entries from each item's session-tracking note. Group by type:

• tool-error — MCP or tool failures
• excessive-roundtrips — more calls than necessary
• workaround — agent had to work around a limitation
• api-confusion — unclear API semantics

Identify themes across entries (e.g., "3 friction entries related to gate failures on items without schemas").

---

Step 4 — Check Trend Memory

Read the trend memory file memory/retrospectives.md from the auto memory directory (file read, not MCP call). The auto memory path is shown at session start — typically ~/.claude/projects/<project-key>/memory/.

If the file does not exist: This is the first retrospective. Skip trend comparison — all findings are new baselines.

If the file exists: For each dimension finding from step 3:

• Search existing trend entries for matches (same schema note, same delegation pattern, same friction type)
• If a finding matches an existing trend, note the incremented session count
• If a finding is new, mark it as a candidate for the trends section

---

Step 5 — Persist the Retrospective

Skip entirely in dry-run mode.

5a. Find or create container

This container is process-global by design — it is the shared, cross-project learning layer, so it deliberately lives outside any project root and this search stays unscoped even when a project rootId is known.

query_items(operation="search", query="Session Retrospectives", limit=5)

If no match with that exact title at depth 0, create it:

manage_items(operation="create", items=[{
  title: "Session Retrospectives",
  summary: "Container for structured post-implementation analyses.",
  type: "container",
  tags: "container",
  priority: "low"
}])

5b. Create retrospective item

If a project rootId (or project name from .taskorchestrator/config.yaml project.name) is known, include it in the title so a shared-DB container holding retrospectives from multiple projects stays attributable:

manage_items(operation="create", items=[{
  title: "Retrospective — <project-name> — <root-item-title> — <YYYY-MM-DD>",
  summary: "<one-sentence summary of key findings>",
  tags: "session-retrospective",
  parentId: "<container-uuid>"
}])

If no project name is known, omit that segment: "Retrospective — <root-item-title> — <YYYY-MM-DD>".

5c. Fill queue-phase notes

The session-retrospective schema has four required notes: three queue-phase (session-metrics, workflow-evaluation, improvement-signals) plus one work-phase actions-taken (a closure record of the proposals created in Step 7). Fill the three queue notes now, in a single batch; actions-taken is filled later, at Step 8b, once the proposals are known:

manage_notes(operation="upsert", notes=[
  {
    itemId: "<retro-uuid>",
    key: "session-metrics",
    role: "queue",
    body: "<Step 3 quantitative data: item counts, outcome distribution, schema usage, token estimates, files changed>"
  },
  {
    itemId: "<retro-uuid>",
    key: "workflow-evaluation",
    role: "queue",
    body: "<Step 3 qualitative assessment: per-dimension scores and key findings>"
  },
  {
    itemId: "<retro-uuid>",
    key: "improvement-signals",
    role: "queue",
    body: "<Step 4 trend analysis: new trends, reinforced trends, proposals>"
  }
])

5d. Advance to work phase

The three queue notes satisfy the queue→work gate. Advance the item to work (the work-phase actions-taken gate stays open until Step 8b):

advance_item(transitions=[{itemId: "<retro-uuid>", trigger: "start"}])

Do not complete the item yet — the actions-taken work-phase note is still required and depends on the Step 7 proposal results. Completion happens at Step 8b.

---

Step 6 — Update Trend Memory

Skip entirely in dry-run mode.

Read memory/retrospectives.md from the auto memory directory. Update each section:

• Schema Effectiveness: Add or update entries from dimension 3a findings. Format: - <schema-note-key>: <observation>. Sessions: N. Last seen: YYYY-MM-DD
• Delegation Patterns: Add or update from dimension 3b. Format: - <pattern>. Sessions: N. Last seen: YYYY-MM-DD
• Note Quality: Add or update from dimension 3c. Format: - <note-key>: <observation>. Sessions: N. Last seen: YYYY-MM-DD
• Improvement Proposals: Add new proposal references if created in step 7.

Write the updated file.

---

Step 7 — Create Improvement Proposals

Skip entirely in dry-run mode.

Check the updated trend memory (from step 6). For each trend with Sessions >= 2:

7a. Find or create proposals container

This container is also process-global by design (same rationale as 5a) — it stays outside any project root, and this search stays unscoped even when a project rootId is known.

query_items(operation="search", query="Improvement Proposals", limit=5)

Create if missing (same pattern as 5a — include type: "container" and tags: "container").

7b. Create proposal items

For each graduating trend:

manage_items(operation="create", items=[{
  title: "Proposal: <concrete change description>",
  summary: "<what to change and why — reference retrospective item IDs that surfaced the trend>",
  tags: "improvement-proposal",
  parentId: "<proposals-container-uuid>",
  priority: "low"
}])

The proposal should include a concrete suggestion — not just "this is a problem" but the specific change:

• Schema edits: include the exact YAML to add/modify
• Skill updates: reference the section and describe the change
• Output style adjustments: specify the zone and content
• Hook additions: specify the event, matcher, and purpose

---

Step 8 — Meta-Evaluation

Skip entirely in dry-run mode.

Query prior retrospectives:

query_items(operation="search", tags="session-retrospective", limit=20)

If 3+ retrospectives exist, evaluate:

1. Trend durability: Did previously identified trends get addressed? Check if improvement proposals in terminal state exist for prior trends.
2. Proposal staleness: Any proposals created 3+ retrospectives ago with no movement (still in queue)?
3. Self-quality: Are retrospective notes converging on useful patterns, or repeating the same observations without resolution? Are notes too verbose (>800 tokens each) or too shallow (<100 tokens)?

If meta-findings warrant it, add a brief note to the current retrospective's improvement-signals note via:

manage_notes(operation="upsert", notes=[{
  itemId: "<current-retro-uuid>",
  key: "improvement-signals",
  role: "queue",
  body: "<updated body with meta-evaluation appended>"
}])

---

Step 8b — Fill Closure Note and Complete

Skip entirely in dry-run mode.

Now that Step 7 has determined which improvement proposals were created (or that none graduated), fill the work-phase actions-taken note — the schema's closure record — and complete the item.

manage_notes(operation="upsert", notes=[{
  itemId: "<retro-uuid>",
  key: "actions-taken",
  role: "work",
  body: "<closure record: improvement-proposal items created/updated in Step 7 (title + short-id each), or 'none graduated (≥2 sessions) this run'; plus trend-memory sections updated and any memory writes>"
}])

The actions-taken note satisfies the work→terminal gate. Complete:

advance_item(transitions=[{itemId: "<retro-uuid>", trigger: "complete"}])

8c. Acknowledge the retrospective to the trigger hooks

Run via Bash, from the skill's base directory shown at invocation (<skill-base-dir>):

node "<skill-base-dir>/../../hooks/retro-ack.mjs"

This stamps the hook dedup marker as handled, extending the suppression window so the Stop backstop does not re-prompt for a retrospective — a manual run completing its own item must not look like a new implementation run needing one. This step is best-effort: if the script is missing (plugin layout changed), continue without failing the retrospective.

---

Step 9 — Report

Render a dashboard using the output style visual conventions:

## Session Retrospective — <root-item-title>

**<YYYY-MM-DD> · <N> items · <N> schemas used**

### Dimension Scores

| Dimension | Score | Key Finding |
|-----------|-------|-------------|
| Schema effectiveness | <fraction or qualitative> | <one-line summary> |
| Delegation alignment | <fraction or "not recorded"> | <one-line summary> |
| Note effectiveness | <qualitative> | <one-line summary> |
| Plan-to-execution | <fraction> | <one-line summary> |
| Friction | <count> entries, <N> themes | <top theme> |

### Trends

| Pattern | Sessions | Status |
|---------|----------|--------|
| <trend description> | N | new / reinforced / addressed |

### Improvement Proposals Created

| ID | Proposal | Trigger |
|----|----------|---------|
| `<short-id>` | <description> | <trend that graduated> |

Conditional prefix:

• Dry-run: **Dry run** — no items created, no memory updated.

Omit sections with no data (e.g., no improvement proposals -> omit that table). If delegation-metadata notes were present, include a delegations count in the header line.

---

Troubleshooting

No session-tracking notes found

• Cause: Implementing agents did not fill their session-tracking notes. This happens when items have no matching note schema (schema-free items skip gate enforcement).
• Solution: Check .taskorchestrator/config.yaml for a default schema that includes session-tracking as a required note. Adding it ensures agents are prompted to fill tracking data.

Schema not recognized (expectedNotes empty)

• Cause: session-retrospective tag not in .taskorchestrator/config.yaml, or MCP not reconnected after config edit
• Solution: Run /mcp to reconnect, verify config has the schema

Trend memory file missing

• Cause: First retrospective ever run
• Solution: Skill creates the file at step 6 with initial structure. No action needed.

Container not found

• Cause: First time creating retrospectives or improvement proposals
• Solution: Skill creates containers lazily at steps 5a and 7a. No action needed.

Retrospective pulled in another project's items

• Cause: Shared multi-project DB with no project scope configured, so the step 1a fallback scan searched globally instead of within the current project's subtree.
• Solution: Configure project.rootId in .taskorchestrator/config.yaml, or pass the root item UUID as an argument to the skill:

project:
  rootId: "<uuid>"
  name: "<project name>"