Thoughtful

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/)

thoughtful-data/
├── config.json          # Your preferences
├── state.json           # Processing state
├── tasks.json           # Pending items, commitments, waiting-on
├── people.json          # Relationship tracking per contact
├── summaries/           # Historical summaries
└── context/             # Conversation context per chat

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. 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. 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

Morning, Neil! ☀️

Here's your WhatsApp catch-up:

🆕 WHAT'S NEW (last 24h):

**Alice is waiting on you** (3 messages)
She's asked about Tuesday's meeting twice now and sent a restaurant link. 
Feels time-sensitive - she mentioned "need to know by tonight."

**Bob's getting urgent** (2 messages)
Those design files he asked for? Now needs them "before EOD." 
This has been pending for 2 days.

**House party group** (12 messages)
Weekend plans firming up. They're organizing who brings what.
Not urgent, but you might want to check in before Saturday.

⏰ STILL PENDING:

- Confirm Tuesday meeting - Alice (**5 days old**, asked 3x)
- Send design files - Bob (urgent, 2 days old)
- Review contract - Lawyer (low priority, 1 week old)

💡 COMMUNICATION INSIGHTS:

**Relationships that need attention:**
- Alice: Tone shifted from casual to "please let me know" - 
  she might be frustrated you haven't confirmed yet
- Bob: This is the second follow-up - shows it's important to him

**Quiet conversations worth reviving:**
- Haven't heard from Priya in 2 weeks (you asked about her project)
- Charlie went quiet after you said you'd think about his idea

📝 SUGGESTED ACTIONS:

**For Alice:**
"Hey! Sorry for the delay - yes, Tuesday works. That restaurant 
looks perfect, let's do 7pm?"

**For Bob:**
"On it - will have files to you by 3pm today. Thanks for the patience!"

**For Priya (re-engage):**
"Hey Priya! Been thinking about that project you mentioned - 
how's it going?"

Did you complete: "Confirm Tuesday meeting with Alice"?
[✅ Done] [⏭️ Still pending] [❌ Won't do] [💬 Draft reply]

First-Time Setup

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

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

2. List available groups

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

3. Configure preferences

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

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

5. Test run

   • Generate first summary to verify setup
   • Deliver via Telegram

Usage

IMPORTANT: All thoughtful operations run in sandbox.

When generating summaries:

1. Use the thoughtful skill
2. Run scripts in sandbox: exec("~/clawd/skills/thoughtful/scripts/generate-summary.sh", {host: "sandbox"})
3. Read generated prompt from thoughtful-data/context/last-prompt.txt
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

{
  "name": "wacli-sync-daily",
  "schedule": {"kind": "cron", "expr": "30 10,17,22 * * *", "tz": "Asia/Calcutta"},
  "sessionTarget": "isolated",
  "payload": {
    "kind": "agentTurn",
    "message": "Run WhatsApp sync:\n\n1. Kill any stuck wacli processes: `pkill -9 wacli-readonly` (sandbox)\n2. Run `wacli-readonly sync` in sandbox (let it complete)\n3. Report: 'WhatsApp sync completed' or any errors",
    "deliver": true,
    "channel": "telegram",
    "to": "-1003893728810:topic:38"
  }
}

Thoughtful Summary (3x daily)

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

{
  "name": "thoughtful-daily",
  "schedule": {"kind": "cron", "expr": "0 11,18,23 * * *", "tz": "Asia/Calcutta"},
  "sessionTarget": "isolated",
  "payload": {
    "kind": "agentTurn",
    "message": "Run thoughtful summary:\n\n1. Kill any stuck wacli processes: `pkill -9 wacli-readonly` (sandbox)\n2. Run `~/clawd/skills/thoughtful/scripts/generate-summary.sh` in sandbox\n3. Read the generated prompt from `thoughtful-data/context/last-prompt.txt`\n4. Create a warm, thoughtful summary following the communication coach framework\n5. Deliver via Telegram to Clawdgroup topic",
    "deliver": true,
    "channel": "telegram",
    "to": "-1003893728810:topic:38"
  }
}

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 ~/clawd/whatsapp/
• 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. 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.