thoughtful

Your thoughtful companion for WhatsApp.

Goes beyond simple message summaries - helps you maintain relationships, catch what's slipping through the cracks, and communicate with intention instead of just reacting.

What It Does

📊 Smart Tracking

• - Pending tasks - action items from any conversation, tracked until complete
• Waiting on - things you asked about, waiting for responses
• Commitments - promises you made, deadlines you mentioned
• Relationship dynamics - sentiment shifts, response patterns, quiet conversations
• Important dates - birthdays, events, deadlines mentioned in chat
• Decisions - choices you made that you might need to remember

🧠 Communication Coaching

Acts as your emotionally intelligent assistant to help you:

• - Catch things left hanging that need reply or closure
• Notice when tone/sentiment shifts in relationships
• Find good moments to check in or express appreciation
• Re-engage quiet conversations without awkwardness
• Stay intentional, not reactive

📝 Daily Summaries

Warm, conversational catch-ups that feel like a friend briefing you, not a robot checklist.

Includes:

• - What's new (last 24h)
• What's still pending (from days/weeks ago)
• Relationship insights
• Suggested conversation starters
• Communication nudges

Storage

All data stored in: ${WORKDIR}/thoughtful-data/ (defaults to ~/clawd/thoughtful-data/)

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Configuration

Interactive Setup (Recommended):
When first using the skill, the agent will guide you through setup via chat:

• - Which WhatsApp groups to track (shows list, you select)
• Priority contacts to always highlight
• Summary timing preferences
• Tracking features to enable/disable

All configuration happens through conversation - no manual file editing needed.

Manual Configuration (Advanced):
Edit ${WORKDIR}/thoughtful-data/config.json to:

• - Add/remove groups from whitelist
• Mark priority contacts
• Adjust tracking preferences
• Set summary timing

Communication Coach Prompting

The skill uses this framework (inspired by littlebird):

Act as a thoughtful communication coach with a practical, emotionally intelligent lens.
Help improve communication in relationships with peers, colleagues, and friends by:

1. 1. Reflecting on interactions - Have I left anything hanging? Has tone shifted?
2. Suggesting check-ins - Good moments to reach out or show appreciation
3. Providing conversation starters - Thoughtful prompts to start/restart conversations
4. Re-engagement guidance - How to re-open quiet conversations without awkwardness

Tone: Clear, warm, and direct. No fluff, not robotic. Practically useful.

How It Works

Data Collection

1. 1. Fetches messages from wacli-readonly (last 24h + older pending items)
2. Processes DMs + whitelisted groups only
3. Extracts action items, sentiment, commitments, dates
4. Updates tracking files

Analysis & Insights

Uses LLM to:

• - Understand conversation context and tone
• Identify what needs attention vs what can wait
• Detect relationship patterns (someone getting frustrated, conversations going quiet)
• Suggest thoughtful responses and check-ins

Summary Generation

Creates warm, human summary with:

• - What's new - fresh messages and action items
• Still pending - older tasks not yet complete
• Relationship insights - "Alice has asked 3 times, might be frustrated"
• Suggested actions - "Good time to check in with Bob"
• Conversation starters - Specific prompts you can send

Interactive Task Management

Summary includes buttons to:

• - ✅ Mark tasks done
• ⏭️ Still pending
• ❌ Won't do
• 💬 Draft reply

Example Summary

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First-Time Setup

When a user first installs the skill, guide them through interactive setup:

1. 1. Authenticate wacli-readonly

- Run wacli-readonly auth --qr-file /tmp/whatsapp-qr.png (in sandbox) - Send QR code image to user - Wait for authentication confirmation

1. 2. List available groups

- Run wacli-readonly groups list (in sandbox) - Show user their WhatsApp groups - Ask which groups to include in summaries

1. 3. Configure preferences

- Ask about priority contacts - Confirm summary timing (default: 11am daily) - Confirm tracking features (sentiment, commitments, etc.)

1. 4. Create cron jobs

- Set up WhatsApp sync cron (10:30 AM, isolated session) - Set up daily summary cron (11:00 AM, isolated session) - Confirm both are scheduled correctly

1. 5. Test run

- Generate first summary to verify setup - Deliver via Telegram

Usage

IMPORTANT: All thoughtful operations run in sandbox.

When generating summaries:

1. 1. Use the thoughtful skill
2. Run scripts in sandbox: INLINECODE6
3. Read generated prompt from INLINECODE7
4. Use OpenClaw's LLM for summary generation
5. Deliver via current channel

The skill will:

• - Fetch messages from wacli-readonly (sandbox)
• Process and analyze conversations
• Generate thoughtful summary using OpenClaw LLM
• Track tasks and relationship insights
• Deliver warm, conversational summary

Cron Setup

IMPORTANT:

• - Always use sessionTarget: "isolated" - runs independently
• Never use sessionTarget: "main" - will not deliver properly
• All operations run in sandbox
• Two crons total: sync + summary, each running 3x daily
• Sync runs 30 minutes before each summary to ensure fresh data

WhatsApp Sync (3x daily)

Runs at 10:30 AM, 5:30 PM, 10:30 PM CODEBLOCK2

Thoughtful Summary (3x daily)

Runs at 11:00 AM, 6:00 PM, 11:00 PM CODEBLOCK3

Why 3x daily?

• - Catch messages throughout the day without missing important updates
• Morning (11 AM): Start your day informed
• Evening (6 PM): Stay on top of afternoon conversations
• Night (11 PM): End-of-day catch-up before bed

Why separate sync + summary?

• - WhatsApp sync can take time and needs fresh data before analysis
• 30-minute gap allows sync to complete before summary generation
• Using comma-separated hours in cron keeps it simple (2 crons total)

Note: The agent will set this up automatically during first-time configuration. Users can adjust the timing during setup.

Privacy & Security

• - All data stored locally in INLINECODE10
• wacli-readonly database in ~/.wacli (read-only, no sending)
• No external services except OpenClaw LLM for summaries
• All operations run in sandbox for isolation

Tracking Features Explained

Sentiment Trends

Detects if someone's tone is shifting:

• - "Getting frustrated" (multiple follow-ups, shorter messages)
• "Going quiet" (reduced frequency, shorter replies)
• "More engaged" (longer messages, asking questions)

Response Time Patterns

Tracks how long you typically take to reply per person:

• - Helps identify if you're slower than usual with someone
• Flags when your delay might be noticed

Recurring Topics

Notices patterns like:

• - "Bob always asks about project updates on Fridays"
• "Alice sends restaurant links before dinner plans"

Commitment Tracking

Extracts promises you made:

• - "I'll send that by Tuesday"
• "Let me think about it and get back to you"
• "I'll check and let you know"

Flags if you haven't followed through.

Important Dates

Catches mentions of:

• - Birthdays, anniversaries
• Deadlines, launch dates
• Meetings, events
• "Next week," "end of month," etc.

Decision Tracking

Remembers choices you made:

• - "Let's go with Option A"
• "I decided not to attend"
• "We agreed on 7pm"

Helps you stay consistent and avoid contradicting yourself later.

Tips for Best Results

1. 1. Whitelist carefully - Only add groups you actively care about
2. Mark priority contacts - VIPs always show in summary
3. Review summaries daily - Interactive task completion keeps tracking accurate
4. Use conversation starters - They're tailored to your actual context
5. Act on relationship insights - Small check-ins prevent bigger issues

Philosophy

This isn't about productivity hacks or inbox zero. It's about staying human in your digital communication:

• - Remember what matters to people
• Show up consistently in relationships
• Communicate with intention, not just reaction
• Catch small things before they become big things

Your relationships deserve better than "sorry, forgot to reply." This helps you be the communicator you want to be.