Deep Wiki: Onboarding Guide Generation

You are creating onboarding documentation for this codebase. Generate four audience-tailored guides in an onboarding/ folder.

Source Repository Resolution (MUST DO FIRST)

Before generating any guides, resolve the source repository context:

1. Check for git remote: Run git remote get-url origin
2. Ask the user: "Is this a local-only repository, or do you have a source repository URL?"
   • Remote URL → store as REPO_URL, use linked citations: [file:line](https://github.com/microsoft/skills/blob/cf77b1efbf3117501f4727c476894751311ee885/.github/plugins/deep-wiki/commands/REPO_URL/blob/BRANCH/file/README.md#Lline)
   • Local → use (file_path:line_number)
3. Determine default branch: Run git rev-parse --abbrev-ref HEAD
4. Do NOT proceed until resolved

Step 1: Language & Technology Detection

Before writing anything, detect:

1. Primary language from file extensions and build files:

   • *.cs/*.csproj → C#, *.py/pyproject.toml → Python, *.go/go.mod → Go
   • *.ts/package.json → TypeScript, *.rs/Cargo.toml → Rust, *.java/pom.xml → Java

2. Comparison language for cross-language explanations:

   • C# → Python, Java → Python, Go → Python, TypeScript → Python
   • Python → JavaScript, Rust → C++ or Go, Swift → TypeScript

3. Key technologies by scanning for:

   • Orleans/Akka → Actor model, Cosmos/Mongo → Document DB, PostgreSQL/MySQL → RDBMS
   • Redis → Caching, Kafka/RabbitMQ/ServiceBus → Messaging, gRPC/GraphQL → API protocol
   • Docker/K8s → Containers

Output Structure

onboarding/
├── index.md                    # Onboarding hub with guide selector table
├── contributor-guide.md        # For new contributors (assumes Python or JS)
├── staff-engineer-guide.md     # For staff/principal engineers
├── executive-guide.md          # For VP/director-level engineering leaders
└── product-manager-guide.md    # For product managers

onboarding/index.md — Onboarding Hub

Generate a landing page with project summary and a guide selector table linking to all 4 guides with audience descriptions and estimated reading times.

Step 2: Generate Contributor Guide

File: onboarding/contributor-guide.mdAudience: Engineers joining the project. Assumes proficiency in Python or JavaScript. Length: 1000–2500 lines. Progressive — each section builds on the last.

Required Structure

Part I: Foundations (skip if repo uses Python or JS)

1. {Primary Language} for Python/JS Engineers — Syntax side-by-side tables, async model, collections, DI, type system. Concrete code comparisons, NOT abstract descriptions.
2. {Primary Framework} for Web Framework Users — Compare to equivalent frameworks. Request pipeline, controllers, routing, config, DI container.
3. {Key Technology 1} from First Principles — The problem it solves, core concepts with comparisons, how THIS system uses it.
4. {Key Technology 2} from First Principles — Same approach for second key technology.

Part II: This Codebase 5. The Big Picture — One-sentence summary, core entities table, architecture graph TB diagram. 6. Domain Model & Data Flow — erDiagram, data invariants, sequenceDiagram for primary request lifecycle. 7. Key Patterns — "If you want to add X, follow this pattern" templates with real code.

Part III: Getting Productive 8. Development Environment Setup — Prerequisites table (Tool, Version, Install Command), step-by-step setup, common mistakes. 9. Your First Task — End-to-end walkthrough of adding a simple feature. 10. Development Workflow — Branch strategy, commit conventions, PR process. Use flowchart diagram. 11. Running Tests — All tests, single file, single test, coverage commands. 12. Debugging Guide — Common issues table: Symptom, Cause, Fix. 13. Common Pitfalls — Mistakes every new contributor makes and how to avoid them.

Appendices

• Glossary (40+ terms)
• Key File Reference (Path, Purpose, Why It Matters, Source)
• Quick Reference Card — Cheat sheet of most-used commands

Key Rules

• Progressive depth: Part I → Part II → Part III. Never reference something before explaining it.
• Concrete over abstract: Code examples from the actual codebase.
• Minimum 5 Mermaid diagrams — each followed by `` comment block
• Every claim has a linked citation
• Every command must be copy-pasteable with expected output

Step 3: Generate Staff Engineer Guide

File: onboarding/staff-engineer-guide.mdAudience: Staff/principal engineers. Deep systems experience, may not know this repo's language. Length: 800–1200 lines. Dense, opinionated, architectural.

Required Sections

1. Executive Summary — What the system is in one dense paragraph. What it owns vs delegates.
2. The Core Architectural Insight — The SINGLE most important concept. Include pseudocode in a DIFFERENT language from the repo.
3. System Architecture — Full Mermaid graph TB diagram (middleware → controllers → services → storage → external). Call out the "heart" of the system.
4. Domain Model — Mermaid erDiagram of core entities. Data invariants table: Entity, Invariant, Enforced By, Source.
5. Component Types & Execution Paths — Table: Component, Type, Execution Path, Key File, Source.
6. Request Lifecycle — Mermaid sequenceDiagram (with autonumber) showing typical request.
7. State Transitions — Mermaid stateDiagram-v2 for domain entities with lifecycle states.
8. Decision Log — Table: Decision, Alternatives Considered, Rationale, Source.
9. Dependency Rationale — Table: Dependency, Purpose, What It Replaced, Source.
10. Storage & Data Architecture — Stores used, data access layer, consistency model. Comparison table.
11. Failure Modes & Error Handling — flowchart for error propagation.
12. API Surface & Protocols — Table: Method, Path, Handler, Auth, Source.
13. Configuration & Feature Flags — Table: Key, Default, Description, Source.
14. Performance Characteristics — Bottlenecks, scaling limits, hot paths.
15. Security Model — Auth, authorization, trust boundaries.
16. Testing Strategy — What's tested, what isn't.
17. Known Technical Debt — Table: Issue, Risk Level, Affected Files, Source.
18. Where to Go Deep — Recommended source file reading order.

Key Rules

• Use pseudocode in a different language to explain concepts
• Use comparison tables to map unfamiliar concepts (e.g., Task<T> = Awaitable[T])
• Dense prose with tables, NOT shallow bullet lists
• Every claim has a linked citation + `` comment blocks after each diagram
• Minimum 5 Mermaid diagrams (architecture, ER, class, sequence, state/flowchart)
• Focus on WHY decisions were made, not just WHAT exists

Step 4: Generate Executive Guide

File: onboarding/executive-guide.mdAudience: VP/director of engineering. Needs capability overview, risk assessment, and investment context — NOT code-level details. Length: 400–800 lines. Strategic, concise, decision-oriented.

Required Sections

1. System Overview — What it does, who uses it, business value (2-3 sentences)
2. Capability Map — Table: Capability, Status (Built/Partial/Planned), Maturity, Dependencies
3. Architecture at a Glance — High-level Mermaid graph LR diagram. Services and deployment units ONLY — no internal code. Focus on team boundaries.
4. Team Topology — Table: Component, Owner, Criticality, Bus Factor
5. Technology Investment Thesis — Table: Technology, Purpose, Alternatives Considered, Risk Level
6. Risk Assessment — Table: Risk, Likelihood, Impact, Mitigation, Owner. Cover reliability, security, scalability, compliance.
7. Cost & Scaling Model — How costs scale with usage. Bottlenecks. When next scaling investment is needed.
8. Dependency Map — Mermaid graph TB showing critical external dependencies. Table: Dependency, Type (Service/Library/Platform), Risk if Unavailable.
9. Key Metrics & Observability — Table: Metric, Current Value, Target, Source
10. Roadmap Alignment — Engineering workstreams mapped to business priorities
11. Technical Debt Summary — Table: Issue, Business Impact, Effort to Fix, Priority (top 5 items)
12. Recommendations — 3-5 actionable recommendations for next quarter, prioritized by impact

Key Rules

• NO code snippets — this guide is for engineering leaders, not coders
• Diagrams at service/team level, not class/function level
• Business language — translate technical concepts into impact (reliability, velocity, cost, risk)
• Tables for every structured finding
• Minimum 3 Mermaid diagrams (architecture overview, dependency map, capability map)
• Every claim backed by evidence — cite wiki sections or source files

Step 5: Generate Product Manager Guide

File: onboarding/product-manager-guide.mdAudience: Product managers and non-engineering stakeholders. Needs to understand capabilities and boundaries — NOT implementation. Length: 400–800 lines. User-centric, feature-focused, constraint-aware.

Required Sections

1. What This System Does — 2-3 sentence elevator pitch in plain language (zero jargon)
2. User Journey Map — Mermaid graph LR or journey diagram showing primary user flows
3. Feature Capability Map — Table: Feature, Status (Live/Beta/Planned/Not Possible), User Behavior, Limitations
4. Data Model (Product View) — Simplified Mermaid erDiagram in business terms (e.g., "A Project has many Documents")
5. Configuration & Feature Flags — Table: Flag, What It Controls, Default, Who Can Change It
6. API Capabilities — Table: Capability, Method, Authentication, Rate Limits (written for integration partners)
7. Performance & SLAs — Table: Operation, Expected Latency, Throughput Limit, Current SLA
8. Known Limitations & Constraints — Table: Limitation, User Impact, Workaround, Planned Fix
9. Data & Privacy — Table: Data Type, Storage Location, Retention, Compliance
10. Glossary — Domain terms in plain language
11. FAQ — 10+ common PM questions, answered concisely

Key Rules

• ZERO engineering jargon — no "middleware", "dependency injection", "ORM"
• User-centric framing — everything described in terms of user experience
• Minimum 3 Mermaid diagrams (user journey, data model, feature map)
• Tables for every structured finding
• If a technical concept must be mentioned, explain it in one plain sentence
• Every claim grounded in evidence

Mermaid Diagram Rules (ALL guides)

ALL diagrams must use dark-mode colors:

• Node fills: #2d333b, borders: #6d5dfc, text: #e6edf3
• Subgraph backgrounds: #161b22, borders: #30363d
• Lines: #8b949e
• If using inline style directives, use dark fills with ,color:#e6edf3
• Do NOT use <br/> in Mermaid labels (use <br> or line breaks)

Validation

After generating each guide, verify:

• All file paths mentioned actually exist in the repo
• All class/method names are accurate (not hallucinated)
• Mermaid diagrams render (no syntax errors)
• No bare HTML-like tags outside code fences — wrap in backticks
• Each guide is appropriate for its audience — no code in Executive/PM guides, no jargon in PM guide

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