Onboarding

COG Onboarding Skill

Purpose

Welcome new users and collect essential information to personalize their COG experience. All configuration is stored as natural markdown files within the vault structure, following COG's philosophy of transparent, editable knowledge.

When to Invoke

• User explicitly requests /onboarding or mentions "onboarding" or "setup COG"
• User is new and hasn't completed onboarding yet
• User wants to update their profile or add new projects
• Any time profile customization is needed

Core Design Principle: Smart, Low-Friction Onboarding

The onboarding MUST feel like a natural conversation, NOT a form to fill out.

Key rules:

• Ask open-ended questions, not option-pickers. Never present numbered lists of choices for the user to pick from.
• Ask as few questions as possible. Infer what you can from context and the user's natural responses.
• Never ask redundant questions. If you can extract the answer from something the user already said, don't ask again.
• Parse intelligently. If someone says "I'm Alex, a PM at a fintech startup tracking Stripe and Plaid", extract: name=Alex, role=PM at fintech startup, watchlist=[Stripe, Plaid]. Don't ask follow-up questions for info already given.
• Confirm, don't re-ask. If you're unsure about something the user said, confirm your interpretation rather than asking the question fresh.

Process Flow

1. Welcome Message

Greet the user warmly and explain what COG is:

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Welcome to COG - your self-evolving second brain powered by Claude + Obsidian + Git!

COG helps you capture thoughts, get daily intelligence briefings, and build knowledge over time - all stored as simple markdown files you own.

Let's get you set up. Tell me a bit about yourself - your name, what you do, and what topics or areas you're most interested in staying sharp on. Feel free to share as much or as little as you'd like.

This single open-ended prompt replaces the old sequential questions. The user can naturally mention their name, role, interests, sources, projects, and competitors all at once - or just share a few things.

2. Check for Existing Profile

Look for 00-inbox/MY-PROFILE.md. If it exists:

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I found an existing COG profile! What would you like to update? Just tell me what you'd like to change - your interests, projects, profile info, or anything else.

Don't present a numbered menu. Let them describe what they want in natural language.

3. Intelligent Information Extraction

After the user responds, extract as much as possible from their natural language:

4. Smart Follow-Up (Only If Needed)

After extracting what you can, check what's missing from the required fields only:

• Name (required)
• Role (required)
• Interests (required - need at least 2-3 topics)

If any required field is missing, ask ONE follow-up that covers all gaps. For example:

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Thanks! I got your name and role. What topics are you most interested in staying updated on? (e.g., AI, startups, design, health - whatever matters to you)

Optional fields (news sources, projects, competitive watch) should NEVER generate follow-up questions. If the user didn't mention them, skip them. They can always add them later by editing the files or running onboarding again.

5. Confirm and Create

Before creating files, briefly confirm what you captured and ask about agent team mode:

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Here's what I've got:

- **Name**: Alex
- **Role**: Product Manager at a fintech startup
- **Interests**: AI/ML, fintech trends, product strategy, UX design
- **Projects**: Payments dashboard revamp
- **Tracking**: Stripe, Plaid

One more thing - COG can run in two modes:
- **Solo mode** (default): I handle everything directly in our conversation.
- **Agent team mode**: I delegate research, analysis, and writing to specialist sub-agents for deeper, more thorough results. Works best with Claude Code.

Which do you prefer? (Solo is great for most people - team mode is for power users who want maximum depth.)

Wait for confirmation, then generate everything. If they say "looks good" or similar, proceed. If they correct something, update and proceed without re-confirming. Default to solo if they don't express a preference.

5.5. Role Pack Matching

After extracting the user's role text in Step 3, scan .claude/roles/*.md for a matching role pack:

1. Read each role pack file's YAML frontmatter (role_id and aliases)
2. Compare the user's extracted role text (case-insensitive) against:
   • Exact role_id match (e.g., "product-manager")
   • Any string in aliases (e.g., "pm", "product lead", "head of product")
   • Fuzzy substring match (e.g., "product manager at a fintech startup" contains "product manager")
3. If a match is found:
   • Store the matched role_id as role_pack in the MY-PROFILE.md frontmatter
   • Present role-specific recommendations:

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   As a [Role Display Name], here are the skills and integrations that'll be most useful for you:
   
   **Recommended skills** (ordered by relevance for your role):
   [List top 5-6 skills from the role pack with the "Why it matters for you" context]
   
   **Recommended integrations**:
   [List integrations from the role pack with role-specific explanations]
   

   • Use the role pack's suggested agent_mode as the default (instead of solo)
4. If no match is found:
   • Set role_pack: custom in MY-PROFILE.md
   • Recommend core skills only (those with roles: [all])
   • Ask about common integrations: "Do you use GitHub, Slack, or any other tools you'd like COG to connect with?"

5.6. Integration Discovery

After role pack matching, set up the user's integration preferences:

1. If a role pack was matched, present its recommended integrations with role-specific context:

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   Based on your role, these integrations would give COG the most context:
   
   [For each integration in role pack:]
   - **[Integration]** — [Why it matters for you, from role pack]
   
   Which of these do you already use? And are there any other tools you'd like to connect?
   

2. Parse the user's response:

   • Services they confirm using → add to Active section of MY-INTEGRATIONS.md
   • Services they don't mention or say no to → add to Disabled section
   • Additional services they mention → add to Active section
   • Always add ElevenLabs to Disabled unless explicitly requested

3. Generate 00-inbox/MY-INTEGRATIONS.md:

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   ---
   type: integrations
   created: YYYY-MM-DD
   tags: ["#integrations", "#config", "#cog"]
   ---
   
   # My Integrations
   
   *COG checks this file before using any external service. Edit anytime.*
   
   ## Active
   [For each confirmed integration:]
   - **[Service]**: [Brief description of how COG uses it]
   
   ## Disabled
   [For each declined/unmentioned integration:]
   - **[Service]**: Skipped during onboarding. Enable anytime by moving to Active section.
   
   ---
   
   *Move services between Active and Disabled sections to control what COG connects to.*
   

4. If no role pack was matched, ask about common integrations conversationally:

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   COG can connect with tools like GitHub, Slack, Linear, Notion, and PostHog for richer analysis. Do you use any of these? (Totally optional - COG works great without them too.)
   

6. Generate Profile Documents

Create the four profile documents using the templates in references/profile-templates.md.

00-inbox/MY-PROFILE.md

00-inbox/MY-INTERESTS.md

03-professional/COMPETITIVE-WATCHLIST.md (only if they mentioned companies/people to track)

For Each Project: 04-projects/[project-slug]/PROJECT-OVERVIEW.md

7. Create Directory Structure

Based on configuration, create personalized structure:

Base Structure (Always):

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00-inbox/
01-daily/
  briefs/
  checkins/
02-personal/
  braindumps/
  development/
  wellness/
03-professional/
  braindumps/
  leadership/
  strategy/
  skills/
04-projects/
05-knowledge/
  consolidated/
  patterns/
  timeline/
  booklets/
06-templates/

Project-Specific (For each listed project):

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04-projects/[project-slug]/
  PROJECT-OVERVIEW.md
  braindumps/
  competitive/
  content/
  planning/
  resources/

8. Create Welcome Guide

Generate: 00-inbox/WELCOME-TO-COG.md

Generate it from the template in references/welcome-guide.md.

9. Wrap-Up (No Menu!)

After setup, summarize what was created and suggest a natural next action:

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You're all set! I've created your profile, interests, and project files. Everything is in your vault and editable anytime.

If you want to jump right in, try a braindump - just tell me what's on your mind and I'll capture it. Or ask for your daily brief to see what's happening in your interest areas today.

Don't present a numbered menu of next actions. Just suggest one or two natural things and let them decide.

Configuration Update Mode

If user runs onboarding after initial setup (MY-PROFILE.md exists):

Don't show a menu. Just ask:

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You've already completed onboarding! What would you like to update? Just tell me what needs changing.

Then intelligently handle whatever they say - whether it's adding projects, changing interests, updating their role, etc.

Success Criteria

Onboarding is successful when:

1. MY-PROFILE.md created in 00-inbox/ with role_pack in frontmatter
2. MY-INTERESTS.md created in 00-inbox/
3. MY-INTEGRATIONS.md created in 00-inbox/ with active/disabled sections
4. Role pack matched (or set to custom) and recommendations presented
5. Project directories and overviews created (if applicable)
6. WELCOME-TO-COG.md guide created with role-specific skill ordering
7. User understands next steps and where their profile is stored

Error Handling

If profile already exists:

• Don't overwrite, offer update mode instead
• Preserve existing content, only append/modify requested sections
• Archive old version to 00-inbox/archive/MY-PROFILE-YYYY-MM-DD.md if starting fresh

If directory creation fails:

• Report which directories couldn't be created
• Provide manual creation instructions
• Continue with rest of setup

If user exits mid-onboarding:

• Create partial profile with note: "Onboarding incomplete - run onboarding skill to finish"
• Save what was collected so far
• Resume from last completed step on next run

Privacy & Data

All configuration data is stored as markdown files in:

• 00-inbox/MY-PROFILE.md - Basic profile with role pack
• 00-inbox/MY-INTERESTS.md - Interest areas
• 00-inbox/MY-INTEGRATIONS.md - Active/disabled external service integrations
• 03-professional/COMPETITIVE-WATCHLIST.md - Competitive tracking
• 04-projects/[project]/PROJECT-OVERVIEW.md - Project details

Benefits of markdown storage:

• Human-readable and editable
• Version controlled with Git
• Searchable in Obsidian
• Linkable from other notes
• No parsing required, just read as text
• Can be archived, moved, organized like any other note

Philosophy

COG's configuration is knowledge, not configuration. By storing preferences as markdown notes:

• They're part of your knowledge base, not hidden config files
• You can link to them, reference them, evolve them
• They have context and can include your own notes
• They're transparent and auditable
• They benefit from all of Obsidian's features (tags, links, search, graph view)

This is "configuration as knowledge" - your preferences are themselves notes in your second brain.