dss/.knowledge/adrs/archived/operational/EXECUTION_CHECKLIST.md

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)

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✅ 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):

• 000-template.md - Reusable ADR template with YAML frontmatter
• 001-use-markdown-adrs-for-dss-architecture-decisions.md - Meta-ADR explaining the decision to use ADRs
• README.md - Team guide on creating and using ADRs

Operational Execution Documents (customize with [PLACEHOLDERS]):

• SLACK_ANNOUNCEMENT_TEMPLATE.md - Two versions (short & long) ready to post
• KICKOFF_AGENDA.md - 30-minute meeting script with full talking points
• FACILITATOR_GUIDE.md - Detailed guide for running the kickoff meeting
• PR_TEMPLATE_UPDATE.md - How to add DSS Principles Check to your PR template

This Checklist:

• EXECUTION_CHECKLIST.md - You are here

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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)

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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

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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?

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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

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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

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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)

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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)

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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

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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

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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)