# DSS Principles Pilot - Execution Checklist

**Status**: All operational documents ready for customization and execution  
**Target Launch**: This week (by Friday 12/12/2025)  
**Pilot Project**: dss_sync_figma  
**Pilot Duration**: 4 weeks (Week 1-4 of December 2025)

---

## ✅ Phase 1: Preparation (You Are Here)

All foundational documents have been created and are ready for customization with your team-specific details.

### Documents in `.knowledge/adrs/`:

**Core Resources** (no customization needed):
- [x] `000-template.md` - Reusable ADR template with YAML frontmatter
- [x] `001-use-markdown-adrs-for-dss-architecture-decisions.md` - Meta-ADR explaining the decision to use ADRs
- [x] `README.md` - Team guide on creating and using ADRs

**Operational Execution Documents** (customize with [PLACEHOLDERS]):
- [x] `SLACK_ANNOUNCEMENT_TEMPLATE.md` - Two versions (short & long) ready to post
- [x] `KICKOFF_AGENDA.md` - 30-minute meeting script with full talking points
- [x] `FACILITATOR_GUIDE.md` - Detailed guide for running the kickoff meeting
- [x] `PR_TEMPLATE_UPDATE.md` - How to add DSS Principles Check to your PR template

**This Checklist**:
- [x] `EXECUTION_CHECKLIST.md` - You are here

---

## Phase 2: Customization (What You Do Next)

Before launching the pilot, customize these documents with your team-specific details:

### Step 1: Prepare Team Information
- [ ] **Identify pilot team members**: Who are the 3 people on dss_sync_figma who'll be test partners?
  - Person 1: [NAME]
  - Person 2: [NAME]
  - Person 3: [NAME]
  
- [ ] **Schedule kickoff meeting**: Pick a time this week
  - **Day**: [DAY - e.g., Thursday]
  - **Date**: [DATE - e.g., Dec 12]
  - **Time**: [TIME - e.g., 2:00 PM] (30 minutes)
  - **Location**: [LOCATION - Zoom link or conference room]

### Step 2: Customize Slack Announcement
- [ ] Open `SLACK_ANNOUNCEMENT_TEMPLATE.md`
- [ ] Fill in all [PLACEHOLDERS]:
  - `[YOUR_TEAM_SLACK_CHANNEL]` - Where to post the message
  - `[PILOT_TEAM_MEMBER_1], [PILOT_TEAM_MEMBER_2], [PILOT_TEAM_MEMBER_3]` - Actual names
  - `[DAY], [DATE], [TIME]` - Your kickoff meeting details
- [ ] **Post to Slack**: 24-48 hours before kickoff meeting
  - Suggested: Post on Tuesday 12/10 if kickoff is Thursday 12/12
  - Use short version (150 words) unless team prefers detailed context
- [ ] Copy-paste the post-kickoff follow-up message somewhere safe for use after meeting

### Step 3: Customize Kickoff Agenda
- [ ] Open `KICKOFF_AGENDA.md`
- [ ] Fill in [PLACEHOLDERS]:
  - `[DATE]` - Kickoff date
  - `[TIME]` - Start and end time
  - `[LOCATION]` - Zoom link or room number
  - `[PILOT TEAM NAMES]` - Your 3 pilot team members
  - `[FACILITATOR NAME]` - Person running the meeting
- [ ] Print this or keep it open on a separate screen during the meeting (it's your reference)

### Step 4: Prepare Facilitator Guide
- [ ] Open `FACILITATOR_GUIDE.md`
- [ ] Fill in [PLACEHOLDERS]:
  - `[YOUR NAME]` - Your name as facilitator
  - `[TEAM MEMBERS]` - Names of pilot team
  - `[DATE & TIME]` - Meeting details
  - `[TEAM MEMBERS]` - (again in places)
- [ ] **Read through the entire guide** (2,500+ lines)
  - Special focus on:
    - Pre-Meeting Checklist (line 11-25) — Complete all items before meeting
    - Section 3: The "First Pancake" (line 145-179) — This is the meeting centerpiece
    - Common Concerns table (line 218-227) — Prepare your responses
- [ ] Set up screen share tools and test them (if running meeting remotely)
- [ ] Have `.knowledge/adrs/` directory open and ready to screen share

### Step 5: Update PR Template
- [ ] Open `PR_TEMPLATE_UPDATE.md`
- [ ] Locate your project's PR template (likely `.github/pull_request_template.md`)
- [ ] Copy the "DSS Principles Check" section from PR_TEMPLATE_UPDATE.md
- [ ] Add it to your PR template **before the Checklist section**
- [ ] Commit the change to git
- [ ] Verify it appears on a test PR draft (optional, but recommended)

### Step 6: Pre-Meeting Checklist (Run Day-of or Day-Before)

From `FACILITATOR_GUIDE.md` lines 11-25:

- [ ] Review `KICKOFF_AGENDA.md` (this is your script)
- [ ] Have `.knowledge/adrs/` open and ready to screen share
- [ ] Open three key files in editor tabs:
  - `000-template.md` (the template)
  - `001-use-markdown-adrs-for-dss-architecture-decisions.md` (the meta-ADR)
  - Your project's updated PR template
- [ ] Have 2-3 example decisions in mind from dss_sync_figma (for "First Pancake" fallback):
  - Example 1: [DECISION - e.g., "How will you handle Figma API token storage?"]
  - Example 2: [DECISION - e.g., "What's your caching strategy for Figma data?"]
  - Example 3: [DECISION - e.g., "Which async library will you use in Python?"]
- [ ] Test your screen share setup (Zoom, Teams, or in-person projector)
- [ ] Print or open the agenda for reference
- [ ] Set a 30-minute timer (hard stop—don't let this run over)

---

## Phase 3: Execution (Week 1 of Pilot)

### Day 1-2: Announcement
- [ ] Post customized Slack announcement to team channel
  - Tag the pilot team members to notify them
  - Include link to `.knowledge/adrs/README.md`

### Day 2-3: Pre-Meeting Prep
- [ ] Send meeting invite to pilot team with:
  - Date/time/location
  - Zoom link (if remote)
  - Calendar note: "30-minute kickoff for ADR pilot — we'll write your first ADR together"
- [ ] Complete "Pre-Meeting Checklist" (above)
- [ ] Mentally prepare your talking points

### Day 3-4: Kickoff Meeting
- [ ] Run the 30-minute kickoff meeting using `KICKOFF_AGENDA.md` + `FACILITATOR_GUIDE.md`
  - Section 1: The "Why" (5 min)
  - Section 2: The "How" (10 min) — Live demo
  - Section 3: The "First Pancake" (10 min) — Write ADR together
  - Section 4: The "Ask" & Next Steps (5 min)
- [ ] Capture the "First Pancake" ADR (save as `002-[title].md` if consensus reached)
- [ ] Note any concerns or questions raised

### Day 4-5: Post-Meeting Followup
- [ ] Send post-meeting Slack message (template in `SLACK_ANNOUNCEMENT_TEMPLATE.md`, lines 98-114)
  - Recap what you covered
  - Remind about next steps (create 1-3 ADRs)
  - Offer to answer questions
- [ ] Create calendar invites for:
  - Week 2-3 check-ins (informal, async or 15-min sync)
  - Week 4 retrospective (30 minutes)
- [ ] Add pilot team to optional Slack thread or workspace for async updates

---

## Phase 3: Piloting (Weeks 2-4)

### Weeks 2-3: ADR Creation
- [ ] Pilot team creates 1-3 ADRs for significant dss_sync_figma decisions
  - They use `000-template.md` as reference
  - They link ADRs in PRs using updated PR template
- [ ] **Facilitator check-in** (informal):
  - Week 2: Brief message asking "How's it going? Any friction?"
  - Week 3: Follow-up if there were concerns

### Week 4: Retrospective
- [ ] Schedule 30-minute retrospective with pilot team
- [ ] Use retrospective questions:
  - ✅ What worked? Did ADRs help capture decisions?
  - ❌ What didn't work? Did it feel burdensome?
  - 🔄 What should change before we roll this out broader?
  - 💡 Would you recommend this for other teams?
- [ ] Document feedback
- [ ] Decide: Refine, expand, or pause the ADR approach?

---

## Critical Success Factors

### For the Kickoff Meeting:
- ✅ **Live demo**: Don't just talk about templates; show them on screen
- ✅ **"First Pancake" exercise**: Write an ADR together in real-time (10 min)
- ✅ **Keep it brief**: Template is tiny; process is lightweight; avoid over-explaining
- ✅ **Honest tone**: "We're experimenting together"—not "here's the new mandate"
- ✅ **Respect their time**: 30 minutes, period. Don't run over

### For Adoption:
- ✅ **Lightness**: ADRs should take 15 minutes max
- ✅ **Clarity**: Only significant decisions (not every PR)
- ✅ **Autonomy**: "Create 1-3 ADRs" is invitation, not requirement
- ✅ **Feedback culture**: Gather honest feedback; be willing to adjust

---

## Contingencies

### If Team is Skeptical During Meeting:
- Reference the Common Concerns table in `FACILITATOR_GUIDE.md` (lines 218-227)
- Use concrete examples from dss_sync_figma
- Emphasize: "We're testing this. Your honest feedback is what makes it work."

### If Time Runs Short:
From `FACILITATOR_GUIDE.md` (lines 240-246):

Priorities (in order):
1. **Never skip the "First Pancake"** (Section 3) — This is the proof point
2. Cut "Show the meta-ADR" if needed — Just say "look at 001 in the repo"
3. Keep "Why" concise — Move to the demo
4. **End on time** — Respect their calendar

### If Pilot Team Doesn't Create ADRs:
- This is valid feedback: the process might be too heavy or not solving a real problem
- Don't force it; capture the feedback in retrospective
- Use Week 4 retro to understand why and adjust

---

## File Location Quick Reference

All ADR-related files are in: **`.knowledge/adrs/`**

| File | Purpose | Who Reads? |
|------|---------|-----------|
| `000-template.md` | ADR template to copy | Pilot team (when creating ADRs) |
| `001-use-markdown-adrs-for-dss-architecture-decisions.md` | Meta-ADR explaining why we use ADRs | Pilot team (during kickoff) |
| `README.md` | Guide on creating & using ADRs | Anyone creating ADRs |
| `SLACK_ANNOUNCEMENT_TEMPLATE.md` | Message to post to team | You (customize & post) |
| `KICKOFF_AGENDA.md` | Meeting agenda + talking points | You + Facilitator (reference during meeting) |
| `FACILITATOR_GUIDE.md` | Detailed facilitator script | Facilitator (read fully before meeting) |
| `PR_TEMPLATE_UPDATE.md` | How to integrate ADRs into PRs | You (customize your PR template) |
| `EXECUTION_CHECKLIST.md` | This document | You (reference as you prep) |

---

## Sign-Off Checklist

Before claiming you're ready to launch:

- [ ] All pilot team members identified and briefed
- [ ] Kickoff meeting scheduled
- [ ] Slack announcement customized and saved (ready to post)
- [ ] Kickoff agenda & facilitator guide reviewed and customized
- [ ] PR template updated and committed to git
- [ ] Pre-meeting checklist items planned (screen share, tabs, timer, etc.)
- [ ] Example dss_sync_figma decisions identified for "First Pancake" fallback
- [ ] Calendar invites created for retrospective (Week 4)

---

## What Happens Next (After Pilot)

**Month 1 Outcome** (Week 4 Retrospective):
- You'll have real feedback on whether ADRs are valuable
- You'll understand what needs to change for broader adoption
- You'll decide: refine, expand, or pivot

**Month 2-3** (If retrospective is positive):
- Share learnings with broader team (tech talk with pilot team as speakers)
- Encourage other teams to try ADRs
- Build simple tooling (e.g., grep queries, dashboard)

**Year 2+**:
- Automated ADR discovery and queries
- Dashboards showing principle adoption
- MCP tools that suggest decisions based on code changes

---

## Questions or Issues?

Refer to the relevant document:
- **How do I run the meeting?** → `FACILITATOR_GUIDE.md`
- **What should I tell the team?** → `SLACK_ANNOUNCEMENT_TEMPLATE.md`
- **What's the ADR format?** → `000-template.md` or `README.md`
- **How do I integrate with PRs?** → `PR_TEMPLATE_UPDATE.md`
- **Why are we doing this?** → `001-use-markdown-adrs-for-dss-architecture-decisions.md`

---

**Document Status**: Ready for execution  
**Created**: 2025-12-08  
**Pilot Team**: dss_sync_figma (identified by you)  
**Target Launch**: This week  
**Next Milestone**: Kickoff meeting (30 min)