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:

Reflecting on interactions - Have I left anything hanging? Has tone shifted?

Suggesting check-ins - Good moments to reach out or show appreciation

Providing conversation starters - Thoughtful prompts to start/restart conversations

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

Fetches messages from wacli-readonly (last 24h + older pending items)
Processes DMs + whitelisted groups only
Extracts action items, sentiment, commitments, dates
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:

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
List available groups
- Run wacli-readonly groups list (in sandbox)
- Show user their WhatsApp groups
- Ask which groups to include in summaries
Configure preferences
- Ask about priority contacts
- Confirm summary timing (default: 11am daily)
- Confirm tracking features (sentiment, commitments, etc.)
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
Test run
- Generate first summary to verify setup
- Deliver via Telegram

Usage

IMPORTANT: All thoughtful operations run in sandbox.

When generating summaries:

Use the thoughtful skill
Run scripts in sandbox: exec("~/clawd/skills/thoughtful/scripts/generate-summary.sh", {host: "sandbox"})
Read generated prompt from thoughtful-data/context/last-prompt.txt
Use OpenClaw's LLM for summary generation
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

Whitelist carefully - Only add groups you actively care about
Mark priority contacts - VIPs always show in summary
Review summaries daily - Interactive task completion keeps tracking accurate
Use conversation starters - They're tailored to your actual context
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.

Thoughtful