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Docs update: comprehensive new-user experience improvements#303

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diberry:squad/new-customer-docs-5
Mar 12, 2026
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Docs update: comprehensive new-user experience improvements#303
bradygaster merged 2 commits intobradygaster:mainfrom
diberry:squad/new-customer-docs-5

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@diberry diberry commented Mar 9, 2026

Summary

Comprehensive documentation overhaul based on the new-user experience audit. Addresses all remaining P0/P1 documentation gaps.

New pages (4)

  • Quick start (\get-started/five-minute-start.md) — 5-minute prove-it-works guide for absolute beginners
  • Architecture (\concepts/architecture.md) — One-page system diagram and component explainer
  • Choose your path (\get-started/choosing-your-path.md) — CLI vs SDK vs Copilot agent decision guide with table
  • Glossary (
    eference/glossary.md) — Key terms defined in one sentence each

Updated pages (3)

  • Troubleshooting — Added quick-fix error table at top (5 common errors with one-line fixes)
  • First session — Added inline jargon definitions (coordinator, spawn, Scribe, Ralph) on first use
  • Navigation — Added all 4 new pages to sidebar in logical positions

Also updated

  • \ est/docs-build.test.ts\ — Added assertions for new pages and concepts section

Quality

  • PAO (DevRel) wrote all content following Microsoft Style Guide
  • PAO reviewed every word in a second pass — 15 issues found and fixed
  • Sentence-case headings, active voice, second person, present tense throughout
  • No .squad/ files included (per contributor directive)

Closes #301

cc @bradygaster

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diberry commented Mar 9, 2026

@bradygaster Ready for review — 4 new docs pages + 3 updates from the new-user experience audit. PAO wrote and reviewed everything against the Microsoft Style Guide. Issue #302 (Node.js version alignment) was filed separately as a follow-up.

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Approved — Comprehensive new-user experience upgrade.

Microsoft Style Guide compliance:

  • Sentence-case headings throughout all new pages
  • Active voice and second person maintained
  • Present tense used consistently
  • Clear, scannable structure

Technical accuracy:

  • Architecture diagram is accurate (coordinator → agents → memory → results)
  • Quick start flow is practical and proven
  • Choosing-your-path decision table correctly distinguishes CLI/Copilot/SDK modes
  • Glossary definitions are precise and cite actual behavior
  • Troubleshooting quick fixes table is immediately useful

Tone:

  • Matches Squad's pragmatic, show-don't-tell voice
  • "Prove it works before you learn anything" (Quick start) is perfect PAO tone
  • No hype, no handwaving — tone ceiling enforced

Navigation:

  • All new pages correctly added to navigation.ts
  • Logical ordering: Quick start → Installation → Choose path → First session
  • Architecture moved to concepts section (correct placement)

DOCS-TEST SYNC:PASSED
New pages added:

  • get-started/five-minute-start.md ✅ (added to EXPECTED_GET_STARTED)
  • get-started/choosing-your-path.md ✅ (added to EXPECTED_GET_STARTED)
  • concepts/architecture.md ✅ (EXPECTED_CONCEPTS array created, added to test)
  • reference/glossary.md ✅ (added to EXPECTED_REFERENCE)

Test updates correctly include all new pages in docs-build.test.ts. Hard rule respected.

Outstanding work:

  • Quick fixes table in troubleshooting is a game-changer
  • Architecture page answers "how does this work?" without handwaving
  • Glossary is practical (1-sentence definitions, alphabetical)
  • First-session.md edits clarify Scribe/Ralph permanence

This is a significant UX improvement. New users now have a clear path from "prove it works" to "understand how it works" to "choose my mode."

— PAO

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✅ Test quality verified — ready to merge

Reviewed all test changes in test/docs-build.test.ts. Everything is in sync with the new documentation files.

Test coverage verification

✅ EXPECTED_GET_STARTED (line 18)

  • Added: five-minute-start, choosing-your-path, migration
  • Matches new files: get-started/five-minute-start.md, get-started/choosing-your-path.md
  • Note: migration.md already existed (not part of this PR), but test now correctly accounts for it

✅ EXPECTED_REFERENCE (line 22)

  • Added: glossary
  • Matches new file: reference/glossary.md

✅ EXPECTED_CONCEPTS (line 28)

  • New array: ['architecture', 'your-team', 'memory-and-knowledge', 'parallel-work', 'github-workflow', 'portability']
  • Matches new file: concepts/architecture.md
  • Matches existing files: your-team.md, memory-and-knowledge.md, parallel-work.md, github-workflow.md, portability.md

✅ getAllMarkdownFiles() (line 46)

  • Updated sections array to include 'concepts' — correct

✅ HTML existence check (line 172)

  • Updated to include EXPECTED_CONCEPTS in the validation loop — correct

Docs-test sync analysis

All 4 new .md files have corresponding test assertions:

  1. five-minute-start → EXPECTED_GET_STARTED ✅
  2. choosing-your-path → EXPECTED_GET_STARTED ✅
  3. glossary → EXPECTED_REFERENCE ✅
  4. architecture → EXPECTED_CONCEPTS ✅

No gaps found. Tests are internally consistent and will pass once this PR is merged.

Quality assessment

  • No stale assertions — all test counts match actual files
  • No untested files — every new .md file has a test entry
  • Proper structure — concepts section added to all relevant places
  • No regression risk — only additive changes, no removals

This is a docs-only PR with proper test coverage. No quality blockers.


FIDO — Quality Owner

diberry added a commit to diberry/squad that referenced this pull request Mar 9, 2026
… recommendations

Session: 2026-03-09T19-16-49Z-docs-consolidation
Requested by: Copilot (Scribe role)

Changes:
- Merged 5 inbox decisions (user directives, McManus docs audit, Keaton config audit)
- Updated decisions.md with progressive disclosure framework and docs work classification
- Appended cross-agent team updates to PAO, FIDO, Procedures history files
- Cleared decision inbox (5 files removed)

Summary:
- PAO approved all 4 docs PRs (bradygaster#318, bradygaster#317, bradygaster#305, bradygaster#303) with docs-test sync verified
- FIDO validated test assertions for 4 new docs files (EXPECTED_CONCEPTS array correct, no gaps)
- Procedures approved human-members.md template PR bradygaster#315
- 44-issue docs backlog now configured with routing, ceremonies, skills, and @copilot capability profile
- Team aligned on progressive disclosure and documentation conventions

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>
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diberry commented Mar 9, 2026

@bradygaster — This PR is ready for your review. CI is green. 🚀

Ab3y pushed a commit to Ab3y/squad that referenced this pull request Mar 10, 2026
…m docs (bradygaster#266, bradygaster#267, bradygaster#303, bradygaster#302)

- Kujan: Export 3-layer OTel API (low/mid/high) from SDK public surface (bradygaster#266)
- Hockney: 21 new OTel integration e2e tests + aspire CLI tests (bradygaster#267)
- Fortier: Wire REPL coordinator routing to CopilotClient with streaming (bradygaster#303)
- McManus: Comprehensive upstream inheritance docs with 6 scenarios (bradygaster#302)
- Keaton: Codebase cleanup audit — 47 findings documented (bradygaster#306)

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>
Ab3y pushed a commit to Ab3y/squad that referenced this pull request Mar 10, 2026
…ning

feat: Wave 1 remaining — OTel API, integration tests, REPL wiring, upstream docs (bradygaster#266, bradygaster#267, bradygaster#303, bradygaster#302)
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Hey @diberry! 👋 We just merged 5 of your other doc PRs (#327, #305, #317, #315, #318) — great work across the board. 🎉

This PR now has merge conflicts from those merges (likely in first-session.md and troubleshooting.md). Could you rebase against main to resolve? Once updated, we'll merge this one too — CI was green and both Flight (Lead) and PAO (DevRel) approved the content.

Thanks for all the docs contributions!

Add 4 new docs pages and update 3 existing:
- New: five-minute-start.md (5-minute quickstart)
- New: architecture.md (how Squad works)
- New: choosing-your-path.md (CLI vs SDK vs Copilot)
- New: glossary.md (key terms reference)
- Update: troubleshooting.md (common errors table)
- Update: first-session.md (jargon definitions)
- Update: navigation.ts (sidebar entries)

Closes bradygaster#301

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>
@diberry diberry force-pushed the squad/new-customer-docs-5 branch from f7f6ccb to 01093e0 Compare March 10, 2026 12:48
diberry pushed a commit to diberry/squad that referenced this pull request Mar 10, 2026
Session: 2026-03-10-adoption-tracking
Requested by: Scribe

Changes:
- Merged 4 decisions from inbox to decisions.md: adoption tracking 3-tier architecture, implementation, append-only governance, ampersand style guide
- Updated Flight and EECOM history.md with team cross-agent updates
- Created orchestration logs for PAO (PR bradygaster#303 rebase), Flight (adoption proposal), EECOM (Tier 1 implementation)
- Created session log documenting adoption tracking architecture finalization
- Deleted decision inbox files after merge
@diberry diberry closed this Mar 12, 2026
@diberry diberry reopened this Mar 12, 2026
@bradygaster bradygaster merged commit b88bd5b into bradygaster:main Mar 12, 2026
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Thanks @diberry !

diberry pushed a commit to diberry/squad that referenced this pull request Mar 12, 2026
Session: 2026-03-10-adoption-tracking
Requested by: Scribe

Changes:
- Merged 4 decisions from inbox to decisions.md: adoption tracking 3-tier architecture, implementation, append-only governance, ampersand style guide
- Updated Flight and EECOM history.md with team cross-agent updates
- Created orchestration logs for PAO (PR bradygaster#303 rebase), Flight (adoption proposal), EECOM (Tier 1 implementation)
- Created session log documenting adoption tracking architecture finalization
- Deleted decision inbox files after merge
diberry pushed a commit to diberry/squad that referenced this pull request Mar 14, 2026
Session: 2026-03-10-adoption-tracking
Requested by: Scribe

Changes:
- Merged 4 decisions from inbox to decisions.md: adoption tracking 3-tier architecture, implementation, append-only governance, ampersand style guide
- Updated Flight and EECOM history.md with team cross-agent updates
- Created orchestration logs for PAO (PR bradygaster#303 rebase), Flight (adoption proposal), EECOM (Tier 1 implementation)
- Created session log documenting adoption tracking architecture finalization
- Deleted decision inbox files after merge
diberry pushed a commit to diberry/squad that referenced this pull request Mar 14, 2026
Session: 2026-03-10-adoption-tracking
Requested by: Scribe

Changes:
- Merged 4 decisions from inbox to decisions.md: adoption tracking 3-tier architecture, implementation, append-only governance, ampersand style guide
- Updated Flight and EECOM history.md with team cross-agent updates
- Created orchestration logs for PAO (PR bradygaster#303 rebase), Flight (adoption proposal), EECOM (Tier 1 implementation)
- Created session log documenting adoption tracking architecture finalization
- Deleted decision inbox files after merge
diberry pushed a commit to diberry/squad that referenced this pull request Mar 17, 2026
Session: 2026-03-10-adoption-tracking
Requested by: Scribe

Changes:
- Merged 4 decisions from inbox to decisions.md: adoption tracking 3-tier architecture, implementation, append-only governance, ampersand style guide
- Updated Flight and EECOM history.md with team cross-agent updates
- Created orchestration logs for PAO (PR bradygaster#303 rebase), Flight (adoption proposal), EECOM (Tier 1 implementation)
- Created session log documenting adoption tracking architecture finalization
- Deleted decision inbox files after merge
bradygaster added a commit that referenced this pull request Mar 18, 2026
* docs: comprehensive new-user experience improvements

Add 4 new docs pages and update 3 existing:
- New: five-minute-start.md (5-minute quickstart)
- New: architecture.md (how Squad works)
- New: choosing-your-path.md (CLI vs SDK vs Copilot)
- New: glossary.md (key terms reference)
- Update: troubleshooting.md (common errors table)
- Update: first-session.md (jargon definitions)
- Update: navigation.ts (sidebar entries)

Closes #301

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: update PAO history with first-session guide structure

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* chore: remove pao/history.md session artifact from PR diff

Reverts .squad/agents/pao/history.md to upstream/main so it no longer
appears in the PR diff.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs(ai-team): Merge adoption tracking decisions and governance rules

Session: 2026-03-10-adoption-tracking
Requested by: Scribe

Changes:
- Merged 4 decisions from inbox to decisions.md: adoption tracking 3-tier architecture, implementation, append-only governance, ampersand style guide
- Updated Flight and EECOM history.md with team cross-agent updates
- Created orchestration logs for PAO (PR #303 rebase), Flight (adoption proposal), EECOM (Tier 1 implementation)
- Created session log documenting adoption tracking architecture finalization
- Deleted decision inbox files after merge

* docs: add scenario and feature guides from Tamir blog analysis

New docs pages derived from public blog post analysis:
- scenarios/ralph-operations.md: outer loop deployment, mutex, logging, alerting
- scenarios/proactive-communication.md: two-way Teams webhooks and scanning
- features/issue-templates.md: squad-aware issue templates, routing labels
- features/reviewer-protocol.md: trust levels section (full/selective/self-managing)
- test/docs-build.test.ts: assertions updated for new pages

All content follows Microsoft Style Guide. No individual repo names — aggregate
references only per owner privacy directive.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: scope Squad docs to framework-only content

Remove ralph-operations.md and proactive-communication.md — both document
infrastructure around Squad (webhooks, WorkIQ, deployment patterns) rather
than Squad itself. Content moves to Squad IRL repo.

Reframe issue-templates.md to clarify GitHub Issue Templates are a platform
feature configured for Squad routing, not a Squad feature.

Litmus test applied: if Squad doesn't ship the code/config, it belongs in IRL.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: add cross-org authentication scenario

Created comprehensive documentation for working across GitHub personal
accounts and GitHub Enterprise Managed Users (EMU):

- New scenario page: scenarios/cross-org-auth.md
  - Three solution approaches: gh auth switch, Copilot instructions,
    Squad skill pattern
  - Git credential helper configuration
  - Common error messages and verification steps

- Updated troubleshooting.md with cross-org auth section
- Updated enterprise-platforms.md authentication section with cross-ref
- Added navigation entry for Cross-Org Auth scenario
- Updated test assertions in docs-build.test.ts

Follows Microsoft Style Guide (sentence-case headings, active voice).
Includes practical examples and cross-references to related pages.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs(ai-team): Merge post-work orchestration — boundary heuristic, content triage, remote access proposal

Session: 2026-03-11T01-27-57-post-work-orchestration
Agents: FIDO (Quality Owner), Flight (Lead)

Changes:
- Orchestration logs for FIDO (test assertion sync fix, commit 6599db6) and Flight (content triage skill)
- Merged 6 decisions from inbox to decisions.md
- Consolidated boundary heuristic: "Squad Ships It" (docs vs IRL) across content-triage skill and PR #331 review
- Added content-triage workflow for external content integration
- Added phased rollout proposal for remote Squad access (Discussions → Copilot → Chat)
- Added PR trust levels spectrum (full/selective/self-managing)
- Cross-agent updates: FIDO, Flight, PAO history.md sync; boundary heuristic shared

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* fix: vitest resolve alias for workspace package mocking

Resolve workspace packages to source in vitest so vi.mock intercepts
correctly. Without this, npm ci installs a duplicate squad-sdk under
squad-cli/node_modules which bypasses the mock.

* feat: add non-blocking version check on CLI startup (Phase 1)

Adds a background update check that runs when the interactive shell starts.
On startup, Squad checks the npm registry for a newer version and displays
a passive notification banner if one is available.

Key design decisions:
- Fire-and-forget: never blocks or delays shell startup
- 24-hour cache: avoids repeated network calls
- 3-second fetch timeout via AbortController
- Opt-out via SQUAD_NO_UPDATE_CHECK=1 env var
- Triple-wrapped error handling: silent on any failure

New file: packages/squad-cli/src/cli/self-update.ts
Modified: packages/squad-cli/src/cli-entry.ts (wired into no-args shell path)

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs(pao): add SCANNABILITY REVIEW hard rule to PAO charter

Adds a mandatory scannability framework for all content reviews:
- Paragraphs: narrative flow, conceptual explanations (3-4 sentences max)
- Bullet lists: features, options, scannable items (parallel structure)
- Tables: comparisons, structured reference data, attribute grids
- Quotes/indents: warnings, callouts, cited material
- Decision test: hunt-for-one-item = convert to bullets/table

PAO applies this on every PR with documentation impact.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* fix(docs): replace ~/.squad/ with platform-specific path references

Closes #343

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* deleted images

* docs(ai-team): v0.8.21 release session logged; npm publish automation merged

Session: 2026-03-07T20-03-20Z-v0821-release
Requested by: Spawn manifest (release coordination)

Changes:
- Logged orchestration outputs for Kobayashi, Hockney, McManus, Rabin
- Logged session summary: v0.8.21 release complete (3,768 tests passing, docs deployed)
- Merged decisions from inbox: npm publish CI directive + Kobayashi's GitHub Actions automation
- Propagated cross-agent updates to affected agents' history.md (Kobayashi, Hockney, McManus, Rabin)

Directives:
- GitHub Actions (publish.yml) is now authoritative for npm publishing; local npm publish deprecated
- Brady must add NPM_TOKEN secret to GitHub repo settings to enable CI-based publishing

* docs(kobayashi): v0.8.21 release gate merge & publish trigger

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: add agent anatomy, cross-agent context, and hiring checklist to your-team concept page

Enriches the existing your-team.md with:
- Anatomy of an agent (AI vs human vs @copilot)
- Cross-agent context propagation
- Hiring an agent developer checklist

Closes #328

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: add human-AI collaboration section to github-workflow concept page

Adds a 'Working with your team' section explaining how humans and AI
agents collaborate through the SDLC: triage, design review,
implementation, PR review, and merge.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: address team review feedback on PR #439

- Fix broken links to memory docs (memory-and-knowledge.md → ../features/memory.md)
- Rename heading to 'Agent anatomy' (noun-first, sentence case)
- De-duplicate Human/AI table — reference existing section, keep @copilot details
- Tighten tone — flatten parenthetical asides
- Trim 'Working with your team' — framework + links, not re-teaching

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: reframe lifecycle table as example, not prescriptive

Clarify that the human-AI lifecycle table is illustrative. Teams
determine their own processes using ceremonies and directives.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* fix: remove duplicate EXPECTED_CONCEPTS declaration

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: add 'Planning your team' checklist before agent anatomy

Pre-init planning checklist with ~10 bullet points covering decisions
new squad owners should make before running squad init. Cross-references
existing sections rather than duplicating content.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* docs: replace personal/repo-level bullet with squad topology guidance

Replace the 'Personal or repo-level squad?' bullet in the Planning your
team checklist with a new bullet about squad topology — how many squads
and where they live relative to repos.

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

---------

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>
Co-authored-by: James Sturtevant <jsturtevant@gmail.com>
Co-authored-by: bradygaster <bradyg@microsoft.com>
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Docs update: comprehensive new-user experience improvements

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