BenAI Obsidian Plugin — Setup + Onboarding

USE WHEN the user runs /setup or asks to set up their vault, bootstrap the assistant, initialize the system, or configure the BenAI Obsidian Plugin.

This is a three-phase process:

• Phase 0: Mode Selection — Ask which OS variant to create
• Phase A: Bootstrap — Create the directory structure and system files for the selected mode
• Phase B: Onboarding — Interview the user and personalize everything

Pre-flight Check

Check if claude.md or CLAUDE.md exists only in the current working directory (do NOT search subdirectories or parent directories — check only the exact CWD path).

• If it exists: The vault is already set up. Ask the user:
  • "This vault is already set up. Would you like to:"
  • Re-run the interview — Keep existing structure, update memory files based on new answers
  • Full reset — Delete everything and start fresh (confirm twice before proceeding)
  • Cancel — Do nothing
• If it does NOT exist: Proceed with full setup (Phase 0 + Phase A + Phase B)

---

Phase 0: Mode Selection

Ask the user to pick a mode by presenting these two options as a simple text question:

What type of vault do you want?

1. Solopreneurs/Professionals — Blends work and personal. Best for solo founders, freelancers, consultants.
2. Business/Teams — Org structure with departments, processes, stakeholders. Best for teams and companies.

Wait for the user to respond before proceeding. Do NOT use AskUserQuestion or any tool — just ask via text output and wait for a reply.

Mode mapping:

• Solopreneurs/Professionals → os-mode: professional
• Business/Teams → os-mode: business

Accept any clear signal: "solo", "professional", "freelancer", "business", "org", "team", etc.

If the user skips or says "I don't know", use Solopreneurs/Professionals (professional mode).

Store the selected mode. It will be written to claude.md frontmatter as os-mode: professional | business.

---

Phase A: Bootstrap

Create the directory structure and write all system files for the selected mode.

Step A.1: Create Directory Structure

All modes share this base:

mkdir -p .claude
mkdir -p Context
mkdir -p Projects
mkdir -p Daily
mkdir -p Resources
mkdir -p Skills

Solopreneurs/Professionals mode adds:

mkdir -p Intelligence/meetings/team-standups
mkdir -p Intelligence/meetings/client-calls
mkdir -p Intelligence/meetings/one-on-ones
mkdir -p Intelligence/meetings/general
mkdir -p Intelligence/competitors
mkdir -p Intelligence/market
mkdir -p Intelligence/decisions
mkdir -p Intelligence/archive

Business mode adds:

mkdir -p Intelligence/meetings/team-standups
mkdir -p Intelligence/meetings/client-calls
mkdir -p Intelligence/meetings/one-on-ones
mkdir -p Intelligence/meetings/board-reviews
mkdir -p Intelligence/meetings/all-hands
mkdir -p Intelligence/meetings/cross-team
mkdir -p Intelligence/meetings/general
mkdir -p Intelligence/competitors
mkdir -p Intelligence/market
mkdir -p Intelligence/decisions
mkdir -p Intelligence/processes
mkdir -p Intelligence/archive
mkdir -p Departments
mkdir -p Teams
mkdir -p Onboarding
mkdir -p Resources/templates

Step A.2: Write System Files from References

Read each reference file and write it to the corresponding local path. The reference files contain the complete content for each system file.

All modes — shared system files:

Reference File	Creates at Local Path
references/settings-json-template.md	./.claude/settings.json
references/claudeignore-template.md	./.claudeignore
references/gitignore-template.md	./.gitignore

Mode-specific claude.md template:

Mode	Reference File	Creates at Local Path
Solopreneurs/Professionals	references/claude-md-template.md	./claude.md
Business	references/claude-md-template-business.md	./claude.md

Mode-specific folder guides:

Mode	Reference File	Creates at Local Path
Solopreneurs/Professionals	references/guide-projects.md	./Projects/_guide.md
Solopreneurs/Professionals	references/guide-daily.md	./Daily/_guide.md
Solopreneurs/Professionals	references/guide-intelligence.md	./Intelligence/_guide.md
Solopreneurs/Professionals	references/guide-skills.md	./Resources/_guide.md
Business	references/guide-projects.md	./Projects/_guide.md
Business	references/guide-daily.md	./Daily/_guide.md
Business	references/guide-intelligence.md	./Intelligence/_guide.md
Business	references/guide-skills.md	./Resources/_guide.md
Business	references/guide-departments.md	./Departments/_guide.md
Business	references/guide-teams.md	./Teams/_guide.md
Business	references/guide-onboarding.md	./Onboarding/_guide.md
Business	references/guide-processes.md	./Intelligence/processes/_guide.md
Solopreneurs/Professionals	references/guide-skills-vault.md	./Skills/_guide.md
Business	references/guide-skills-vault.md	./Skills/_guide.md

For each row applicable to the selected mode: read the reference file, then write its content to the local path.

Step A.3: Initialize Starter Context Files

All modes — create placeholder skill folders:

mkdir -p Skills/linkedin-writer/references
mkdir -p Skills/newsletter-writer/references

Then write placeholder files from references:

• Read references/skills-placeholder-linkedin-notes.md → write to ./Skills/linkedin-writer/notes.md
• Read references/skills-placeholder-linkedin-example.md → write to ./Skills/linkedin-writer/references/example-post.md
• Read references/skills-placeholder-newsletter-strategy.md → write to ./Skills/newsletter-writer/strategy.md
• Read references/skills-placeholder-newsletter-example.md → write to ./Skills/newsletter-writer/references/example-edition.md

Solopreneurs/Professionals mode:

• Read references/context-me.md → write to ./Context/me.md

Business mode:

• Read references/context-operator.md → write to ./Context/operator.md
• Read references/context-organization.md → write to ./Context/organization.md
• Read references/context-team.md → write to ./Context/team.md
• Read references/context-strategy-business.md → write to ./Context/strategy.md

Business mode — placeholder teams:

mkdir -p Teams/engineering
mkdir -p Teams/marketing
mkdir -p Teams/leadership

Then write placeholder files from references:

• Read references/teams-placeholder-engineering-readme.md → write to ./Teams/engineering/README.md
• Read references/teams-placeholder-person.md → write to ./Teams/engineering/alice-smith.md
• Read references/teams-placeholder-person.md → write to ./Teams/engineering/bob-jones.md
• Read references/teams-placeholder-engineering-readme.md → write to ./Teams/marketing/README.md
• Read references/teams-placeholder-person.md → write to ./Teams/marketing/carol-white.md
• Read references/teams-placeholder-engineering-readme.md → write to ./Teams/leadership/README.md
• Read references/teams-placeholder-person.md → write to ./Teams/leadership/dave-chen.md

Step A.4: Make Hooks Executable

chmod +x .claude/hooks/*.sh

Step A.5: Confirm Bootstrap

Tell the user:

• "Vault structure created successfully in [mode] mode."
• List the main folders created (varies by mode), including Skills/
• Recommend opening this folder as a vault in Obsidian
• Recommend installing TaskNotes community plugin if they want task management features
• Note that Bases (native database views) are built into Obsidian — no plugin needed for queries
• Mention Resources/ for storing prompts, frameworks, swipe files, and templates
• "Now let's personalize it for you."

Then proceed to Phase B.

---

Phase B: Onboarding

Two questions. That's it. The questions differ by mode.

Mode-specific Questions

Solopreneurs/Professionals mode:

Question 1:

Tell me about yourself (and your business, if you have one). Paste anything — bio, LinkedIn, company about page, team info, whatever you have. You can also upload files. Or skip this.

Question 2:

What are you currently working on? List your active projects, or paste project briefs, docs, whatever. Skip if you'd rather add these later.

Business mode:

Question 1:

Tell me about your organization — company info, team wiki, org chart, product info. Paste, upload, or skip.

Question 2:

What are the active projects or initiatives? Roadmaps, OKRs, briefs — whatever you have. Or skip.

The user might give you:

• A short sentence
• A wall of text (wiki, about page, LinkedIn profile)
• Uploaded files (PDFs, docs, screenshots)
• Nothing ("skip")

Accept whatever they give. Don't ask follow-ups. Extract what you can.

If the user says "skip" to both — proceed to build with defaults only.

---

Phase B Build: Personalize the Vault

After the two questions (or skips), build everything you can from what the user gave you. Work silently — don't narrate each step.

Build Step 1: Create Context Files

Behavior depends on selected mode.

Solopreneurs/Professionals mode:

• Context/me.md — Always created. Fill with identity info from Question 1.
• Context/business.md — Only if user mentioned a company/product/business. Read references/context-business.md as template.
• Context/team.md — Only if user mentioned team members. Read references/context-team.md as template.
• Context/brand.md — Only if user mentioned voice/tone/brand. Read references/context-brand.md as template.
• Context/strategy.md — Only if user mentioned goals/vision/priorities. Read references/context-strategy.md as template.

Business mode:

• Context/operator.md — Always created. Fill with the person's role, decision authority, responsibilities from Question 1. Read references/context-operator.md as template.
• Context/organization.md — Always created. Fill with company info, org structure, products from Question 1. Read references/context-organization.md as template.
• Context/team.md — Always created. Fill with any team members mentioned. Read references/context-team.md as template.
• Context/strategy.md — Always created. Fill with any goals, OKRs, targets mentioned. Read references/context-strategy.md as template. Focus template on OKRs, department goals, revenue targets.
• Context/brand.md — Only if user mentioned voice/tone/brand. Read references/context-brand.md as template.
• Context/stakeholders.md — Only if user mentioned vendors, partners, investors, board. Read references/context-stakeholders.md as template.

Build Step 2: Create Project Folders

From Question 2, intelligently structure each project based on what the user gave you.

Analyze the info and decide the right structure:

• Simple mention ("working on a podcast") → just a README.md
• Moderate detail (scope, deadlines, people) → README.md + relevant subdirs
• Rich info (briefs, specs, research, multiple workstreams) → full structure with subdirs and files

Create subdirectories only when the content justifies them:

Content type	Goes to
Overview, status, deadlines, contacts	README.md
Research, competitor analysis, references	research/{topic}.md
Specs, requirements, briefs	specs/{name}.md or briefs/{name}.md
Drafts, scripts, written content	drafts/{name}.md
Ideas, brainstorms	ideas/{name}.md
Notes, working docs	notes/{name}.md

README.md is always the index:

---
type: project
status: active
created: YYYY-MM-DD
---
## Overview
[What this project is]

## Current Status
[Where things stand]

## Key Resources
[Links, tools, contacts]

## Next Steps
[What needs to happen]

Don't create empty subdirs. Don't cram everything into the README. Distribute content into the right files based on what it actually is.

Business mode only — if user provided department info, also create Departments/{name}/README.md with department charter, KPIs, and team members.

Build Step 3: Mode-specific Additional Setup

Business mode only:

• If user mentioned processes or SOPs, create them in Intelligence/processes/
• If user mentioned onboarding docs, create them in Onboarding/

Build Step 4: Create First Daily Note

Create Daily/YYYY-MM-DD.md (today's date):

---
type: daily-note
date: YYYY-MM-DD
---
# YYYY-MM-DD

## Session
- **Focus**: Initial vault setup and onboarding
- **Completed**: Full vault bootstrap + personalized onboarding
- **Next Steps**: [based on what was discussed]

Build Step 5: Confirm Completion

Tell the user:

• Quick summary of what was created (which context files, how many projects, any departments)
• "Open this folder in Obsidian to see your vault"
• Key command: /assistant (sessions, daily reviews, tasks, meetings)
• "You can add more context anytime — just tell me and I'll update the right files."
• Suggest a next action based on what they told you

Guidelines

• Phase 0 is one question — mode selection
• Phase A is fully automated — no user input needed
• Phase B is exactly 2 questions — no follow-ups, no drilling deeper
• Accept any format: text, pasted docs, uploaded files, or nothing
• Extract as much as you can from whatever the user provides
• Only create context files that have real content — don't create empty placeholder files
• Use the user's actual project names, not generic placeholders
• Don't narrate every file you're creating — just build it and summarize at the end