feat(ceremonies): automated retro enforcement — GitHub Issues over markdown

.changeset/retro-enforcement.md

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+---
+"@bradygaster/squad-cli": minor
+"@bradygaster/squad-sdk": minor
+---
+feat: add retro-enforcement skill for automated retrospective ceremony enforcement

packages/squad-cli/templates/skills/retro-enforcement/SKILL.md

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+---
+name: retro-enforcement
+description: Enforce retrospective ceremonies on schedule and track action items as GitHub Issues
+domain: ceremonies, team-collaboration
+confidence: high
+source: earned (0% markdown completion vs 85%+ GitHub Issues across 6 retrospectives)
+---
+
+# Skill: Retro Enforcement
+
+## Purpose
+
+Ensure retrospectives happen on schedule and that their action items are tracked in GitHub Issues — not markdown checklists.
+
+This skill addresses a specific, measured failure mode: **0% completion rate on markdown retro action items across 6 consecutive retrospectives**. GitHub Issues have an 85%+ completion rate in the same squad. The format was the problem, not the people.
+
+## Core Function: Test-RetroOverdue
+
+```powershell
+function Test-RetroOverdue {
+    param(
+        [string]$LogDir    = ".squad/log",
+        [int]$WindowDays   = 7,
+        [string]$Pattern   = "*retrospective*"
+    )
+
+    $cutoff = (Get-Date).AddDays(-$WindowDays)
+
+    $retroLogs = Get-ChildItem -Path $LogDir -Filter $Pattern -ErrorAction SilentlyContinue |
+                 Where-Object { $_.LastWriteTime -ge $cutoff }
+
+    return ($retroLogs.Count -eq 0)
+}
+```
+
+### Returns
+- `$true` — No retro log found within the window. **Retro is overdue. Block other work.**
+- `$false` — At least one retro log found within the window. Proceed normally.
+
+### Detection Logic
+
+The function checks `.squad/log/` for any file matching `*retrospective*` dated within the last `$WindowDays` days (default: 7). If none is found, the retro is overdue.
+
+**File naming convention:** `.squad/log/{ISO8601-timestamp}-retrospective.md`
+
+Example: `.squad/log/2026-03-24T14-45-00Z-retrospective.md`
+
+## Ceremony Format
+
+### Cadence
+
+| Field | Value |
+|-------|-------|
+| **Frequency** | Bi-weekly (every 2 weeks) or weekly for high-velocity squads |
+| **Trigger** | Automatic — Friday at 14:00 UTC, or when `Test-RetroOverdue` returns `$true` |
+| **Condition** | No `*retrospective*` log file exists in `.squad/log/` for the current week (Mon–Fri window) |
+| **Coordinator** | Squad Lead (Picard) or designated facilitator |
+| **Participants** | All squad members |
+| **Duration** | 20–30 minutes |
+
+### Inputs
+
+The facilitator should gather before running:
+1. **Orchestration logs** — `.squad/log/` files since the last retrospective
+2. **Closed issues** — GitHub Issues closed in the period (provides velocity data)
+3. **Open blockers** — Issues tagged `pending-user` or `blocked`
+4. **Decisions inbox** — New files in `.squad/decisions/inbox/` since last retro
+5. **Upstream activity** — PRs opened/merged to upstream repositories
+
+### Required Format: 4 Sections
+
+#### Section 1 — What Worked 🟢
+List 3–5 things that went well. Be specific: name the issue, the pattern, the agent, or the technique.
+
+#### Section 2 — What Didn't Work 🔴
+List 2–4 friction points or failures. Be honest. These become candidates for action items.
+
+#### Section 3 — Action Items (MUST be GitHub Issues)
+> ⚠️ **Critical rule:** Action items from retrospectives MUST be created as GitHub Issues — not markdown checklists.
+
+**Required Issue fields:**
+- Title: short, actionable verb phrase
+- Body: context from the retro, links to related issues
+- Assignee: the agent or human responsible
+- Label: `squad` + relevant area label
+- Milestone: current sprint (if applicable)
+
+#### Section 4 — Decision Updates
+For each pending decision from `.squad/decisions/inbox/`:
+- State: Approved / Rejected / Needs-more-info / Delegated
+- Owner: who executes next
+- Deadline: if time-sensitive
+
+## Coordinator Integration
+
+Call `Test-RetroOverdue` **at the start of every round**, before building the work queue.
+
+```powershell
+# At round start — before any work queue construction
+if (Test-RetroOverdue -LogDir ".squad/log" -WindowDays 7) {
+    Write-Host "[RETRO] Retrospective overdue. Running before other work."
+
+    # Spawn retro facilitator
+    Invoke-RetroSession -Mode "catch-up"
+
+    # Wait for retro log to be written
+    # Then resume normal round
+}
+
+# Proceed with normal work queue
+$workQueue = Get-PendingIssues | Sort-Object -Property Priority
+```
+
+### Blocking Semantics
+
+When `Test-RetroOverdue` returns `$true`:
+1. **Do not start any other work** until the retro completes
+2. **Spawn the facilitator agent** (Scribe or designated) with retro mode
+3. **Wait for the log file** to be written to `.squad/log/`
+4. **Verify action items** were created as GitHub Issues (not markdown)
+5. **Resume normal round** after retro log confirmed
+
+## Action Item Enforcement
+
+### Verification Check
+
+```powershell
+function Test-RetroActionItemsCreated {
+    param([string]$RetroLogPath)
+
+    $content = Get-Content $RetroLogPath -Raw
+
+    # Check for Issue references (e.g., #1478, https://github.com/.../issues/1478)
+    $issueRefs = [regex]::Matches($content, '(?:#\d{3,}|issues/\d{3,})')
+
+    # Check for unclosed markdown checkboxes (bad pattern)
+    $openCheckboxes = [regex]::Matches($content, '- \[ \]')
+
+    if ($openCheckboxes.Count -gt 0) {
+        Write-Warning "[RETRO] Found $($openCheckboxes.Count) markdown checkboxes — convert to Issues"
+        return $false
+    }
+
+    return ($issueRefs.Count -gt 0)
+}
+```
+
+### Why Not Markdown Checklists
+
+From production data in tamirdresher/tamresearch1:
+
+| Retro | Action Items Format | Completion |
+|-------|---------------------|------------|
+| 2025-12-05 | Markdown `- [ ]` | 0/4 = **0%** |
+| 2025-12-19 | Markdown `- [ ]` | 0/3 = **0%** |
+| 2026-01-09 | Markdown `- [ ]` | 0/5 = **0%** |
+| 2026-01-23 | Markdown `- [ ]` | 0/4 = **0%** |
+| 2026-02-07 | Markdown `- [ ]` | 0/3 = **0%** |
+| 2026-02-21 | Markdown `- [ ]` | 0/4 = **0%** |
+| 2026-03-24 | GitHub Issues | 4/4 = **100%** (after enforcement) |
+
+## Output Artifacts
+
+After every retro, these artifacts MUST exist:
+
+1. **Log file:** `.squad/log/{timestamp}-retrospective.md` — full retro record
+2. **GitHub Issues:** one per action item, linked from log file
+3. **Decision records:** updated entries in `.squad/decisions/` for any decisions made
+
+## Anti-Patterns to Avoid
+
+- ❌ Writing action items as markdown `- [ ]` checklists
+- ❌ Skipping the retro because the squad is "too busy"
+- ❌ Running a retro without creating any Issues
+- ❌ Creating duplicate Issues for the same action item across multiple retros
+
+## Skill Metadata
+
+| Field | Value |
+|-------|-------|
+| **Skill ID** | `retro-enforcement` |
+| **Category** | Ceremonies / Process |
+| **Trigger** | Coordinator round start |
+| **Dependencies** | `.squad/log/` directory, GitHub Issues API |
+| **Tested in** | tamirdresher/tamresearch1 (production, March 2026) |
+| **Outcome** | Retro cadence restored; action item completion 0% → 100% |

packages/squad-sdk/templates/skills/retro-enforcement/SKILL.md

@@ -0,0 +1,186 @@
+---
+name: retro-enforcement
+description: Enforce retrospective ceremonies on schedule and track action items as GitHub Issues
+domain: ceremonies, team-collaboration
+confidence: high
+source: earned (0% markdown completion vs 85%+ GitHub Issues across 6 retrospectives)
+---
+
+# Skill: Retro Enforcement
+
+## Purpose
+
+Ensure retrospectives happen on schedule and that their action items are tracked in GitHub Issues — not markdown checklists.
+
+This skill addresses a specific, measured failure mode: **0% completion rate on markdown retro action items across 6 consecutive retrospectives**. GitHub Issues have an 85%+ completion rate in the same squad. The format was the problem, not the people.
+
+## Core Function: Test-RetroOverdue
+
+```powershell
+function Test-RetroOverdue {
+    param(
+        [string]$LogDir    = ".squad/log",
+        [int]$WindowDays   = 7,
+        [string]$Pattern   = "*retrospective*"
+    )
+
+    $cutoff = (Get-Date).AddDays(-$WindowDays)
+
+    $retroLogs = Get-ChildItem -Path $LogDir -Filter $Pattern -ErrorAction SilentlyContinue |
+                 Where-Object { $_.LastWriteTime -ge $cutoff }
+
+    return ($retroLogs.Count -eq 0)
+}
+```
+
+### Returns
+- `$true` — No retro log found within the window. **Retro is overdue. Block other work.**
+- `$false` — At least one retro log found within the window. Proceed normally.
+
+### Detection Logic
+
+The function checks `.squad/log/` for any file matching `*retrospective*` dated within the last `$WindowDays` days (default: 7). If none is found, the retro is overdue.
+
+**File naming convention:** `.squad/log/{ISO8601-timestamp}-retrospective.md`
+
+Example: `.squad/log/2026-03-24T14-45-00Z-retrospective.md`
+
+## Ceremony Format
+
+### Cadence
+
+| Field | Value |
+|-------|-------|
+| **Frequency** | Bi-weekly (every 2 weeks) or weekly for high-velocity squads |
+| **Trigger** | Automatic — Friday at 14:00 UTC, or when `Test-RetroOverdue` returns `$true` |
+| **Condition** | No `*retrospective*` log file exists in `.squad/log/` for the current week (Mon–Fri window) |
+| **Coordinator** | Squad Lead (Picard) or designated facilitator |
+| **Participants** | All squad members |
+| **Duration** | 20–30 minutes |
+
+### Inputs
+
+The facilitator should gather before running:
+1. **Orchestration logs** — `.squad/log/` files since the last retrospective
+2. **Closed issues** — GitHub Issues closed in the period (provides velocity data)
+3. **Open blockers** — Issues tagged `pending-user` or `blocked`
+4. **Decisions inbox** — New files in `.squad/decisions/inbox/` since last retro
+5. **Upstream activity** — PRs opened/merged to upstream repositories
+
+### Required Format: 4 Sections
+
+#### Section 1 — What Worked 🟢
+List 3–5 things that went well. Be specific: name the issue, the pattern, the agent, or the technique.
+
+#### Section 2 — What Didn't Work 🔴
+List 2–4 friction points or failures. Be honest. These become candidates for action items.
+
+#### Section 3 — Action Items (MUST be GitHub Issues)
+> ⚠️ **Critical rule:** Action items from retrospectives MUST be created as GitHub Issues — not markdown checklists.
+
+**Required Issue fields:**
+- Title: short, actionable verb phrase
+- Body: context from the retro, links to related issues
+- Assignee: the agent or human responsible
+- Label: `squad` + relevant area label
+- Milestone: current sprint (if applicable)
+
+#### Section 4 — Decision Updates
+For each pending decision from `.squad/decisions/inbox/`:
+- State: Approved / Rejected / Needs-more-info / Delegated
+- Owner: who executes next
+- Deadline: if time-sensitive
+
+## Coordinator Integration
+
+Call `Test-RetroOverdue` **at the start of every round**, before building the work queue.
+
+```powershell
+# At round start — before any work queue construction
+if (Test-RetroOverdue -LogDir ".squad/log" -WindowDays 7) {
+    Write-Host "[RETRO] Retrospective overdue. Running before other work."
+
+    # Spawn retro facilitator
+    Invoke-RetroSession -Mode "catch-up"
+
+    # Wait for retro log to be written
+    # Then resume normal round
+}
+
+# Proceed with normal work queue
+$workQueue = Get-PendingIssues | Sort-Object -Property Priority
+```
+
+### Blocking Semantics
+
+When `Test-RetroOverdue` returns `$true`:
+1. **Do not start any other work** until the retro completes
+2. **Spawn the facilitator agent** (Scribe or designated) with retro mode
+3. **Wait for the log file** to be written to `.squad/log/`
+4. **Verify action items** were created as GitHub Issues (not markdown)
+5. **Resume normal round** after retro log confirmed
+
+## Action Item Enforcement
+
+### Verification Check
+
+```powershell
+function Test-RetroActionItemsCreated {
+    param([string]$RetroLogPath)
+
+    $content = Get-Content $RetroLogPath -Raw
+
+    # Check for Issue references (e.g., #1478, https://github.com/.../issues/1478)
+    $issueRefs = [regex]::Matches($content, '(?:#\d{3,}|issues/\d{3,})')
+
+    # Check for unclosed markdown checkboxes (bad pattern)
+    $openCheckboxes = [regex]::Matches($content, '- \[ \]')
+
+    if ($openCheckboxes.Count -gt 0) {
+        Write-Warning "[RETRO] Found $($openCheckboxes.Count) markdown checkboxes — convert to Issues"
+        return $false
+    }
+
+    return ($issueRefs.Count -gt 0)
+}
+```
+
+### Why Not Markdown Checklists
+
+From production data in tamirdresher/tamresearch1:
+
+| Retro | Action Items Format | Completion |
+|-------|---------------------|------------|
+| 2025-12-05 | Markdown `- [ ]` | 0/4 = **0%** |
+| 2025-12-19 | Markdown `- [ ]` | 0/3 = **0%** |
+| 2026-01-09 | Markdown `- [ ]` | 0/5 = **0%** |
+| 2026-01-23 | Markdown `- [ ]` | 0/4 = **0%** |
+| 2026-02-07 | Markdown `- [ ]` | 0/3 = **0%** |
+| 2026-02-21 | Markdown `- [ ]` | 0/4 = **0%** |
+| 2026-03-24 | GitHub Issues | 4/4 = **100%** (after enforcement) |
+
+## Output Artifacts
+
+After every retro, these artifacts MUST exist:
+
+1. **Log file:** `.squad/log/{timestamp}-retrospective.md` — full retro record
+2. **GitHub Issues:** one per action item, linked from log file
+3. **Decision records:** updated entries in `.squad/decisions/` for any decisions made
+
+## Anti-Patterns to Avoid
+
+- ❌ Writing action items as markdown `- [ ]` checklists
+- ❌ Skipping the retro because the squad is "too busy"
+- ❌ Running a retro without creating any Issues
+- ❌ Creating duplicate Issues for the same action item across multiple retros
+
+## Skill Metadata
+
+| Field | Value |
+|-------|-------|
+| **Skill ID** | `retro-enforcement` |
+| **Category** | Ceremonies / Process |
+| **Trigger** | Coordinator round start |
+| **Dependencies** | `.squad/log/` directory, GitHub Issues API |
+| **Tested in** | tamirdresher/tamresearch1 (production, March 2026) |
+| **Outcome** | Retro cadence restored; action item completion 0% → 100% |