First Interaction

• Ask what they're tracking: clients, leads, investors, job contacts, networking — context shapes schema
• Ask their technical comfort: spreadsheets, JSON, databases — determines starting format
• Create ~/crm/ folder as the single source of truth

Start With Files, Not Apps

• JSON or CSV for first version — validate data model before adding complexity
• Single file contacts.json initially — resist creating multiple files until needed
• Don't suggest web app until they've used files for at least a week
• Don't suggest database until files feel slow or limiting

Minimal Contact Schema

• id, name, email, company, phone, notes, tags, created, updated — nothing more initially
• tags array over rigid categories — flexible, no schema changes needed
• notes field is often the most valuable — encourage freeform context
• Generate UUID for id, not auto-increment — survives merges and imports

When To Add Interactions File

• User asks "when did I last talk to X" — signal they need history
• Separate file linked by contact_id — not nested in contact object
• type field (note/email/call/meeting) enables filtering later
• Always include date — timeline view is essential

When To Add Companies File

• Multiple contacts at same company — signal to separate
• Many-to-many: one person can work at multiple companies over time
• company_id in contacts, not company name duplication

When To Add Deals/Opportunities

• User mentions "pipeline", "stage", "close date", "deal value"
• Link to contact_id and optionally company_id
• Stages as simple string field initially — don't over-engineer state machine

SQLite Migration Triggers

• File operations feel slow (>100 contacts typically)
• User wants to query/filter in complex ways
• Multiple users need access (SQLite handles concurrent reads)
• Offer to write migration script — don't force manual re-entry

Progressive Timeline

• Week 1: contacts file only, prove they'll use it
• Week 2: add interactions when they want history
• Week 3: add tags, search helper script
• Month 2: companies file if needed
• Month 3: deals file if tracking opportunities
• Only then: consider web UI or more complex tooling

What NOT To Suggest Early

• Web application — massive scope increase, validate data model first
• Email sync/integration — suggest BCC/forward workflow, much simpler
• Calendar integration — manual logging is fine initially
• Authentication — single-user local CRM doesn't need it
• Mobile app — sync complexity not worth it early

Helper Scripts Worth Offering

• Quick add from command line — reduces friction
• Search across all files — grep/jq one-liner
• Backup to timestamped zip — essential before migrations
• Export to CSV — for users who want spreadsheet view

Data Integrity Habits

• Backup before any bulk edit or migration
• Check for duplicate emails before adding contact
• Validate email format on entry
• Keep created/updated timestamps — debugging lifesaver

Sync When Asked

• Cloud folder (Dropbox/iCloud/Drive) for multi-device — simplest
• Git repo for version history — good for technical users
• Don't suggest complex sync solutions until files prove insufficient