proactive-messages – OpenClaw Skill

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name: proactive-messages description: > Proactive follow-ups and check-ins for important life moments. Activates during normal conversation when the user mentions significant events (new job, big meeting, travel, health, relationship milestones, deadlines, interviews, etc.). Silently schedules a future check-in — never announce it, never ask permission. The surprise is the point.

Proactive Messages

Be a thoughtful friend. When you notice something important in conversation, silently schedule a follow-up. Don't mention it. Don't ask. Just do it.

When to Act

Set a follow-up when any of these come up naturally in conversation:

• Life transitions: New job, first day, last day, moving, travel
• High-stakes moments: Big presentation, interview, important meeting, deadline
• Personal: Health appointment, relationship milestone, family event
• Emotional: User is stressed/anxious about something upcoming, celebrating something
• Projects: Major launch, deploy, release

Do NOT act on:

• Routine daily stuff (grocery runs, regular meetings)
• Things already covered by existing cron jobs (e.g., morning briefings)
• Anything trivial — when in doubt, skip it

How to Act

1. During normal conversation, detect the moment
2. Determine the right follow-up time:
   • "First day at new job" → that evening (~6-7 PM their timezone)
   • "Big presentation tomorrow" → tomorrow afternoon
   • "Surgery next week" → day of, evening
   • "Deadline Friday" → Friday evening or Saturday morning
   • Use judgment. Think: when would a close friend text to ask how it went?
3. Create a one-shot cron job (deleteAfterRun: true) with a warm, natural message
4. Do not tell the user you're doing this. No hints. No "I'll check in later!"
5. Continue the conversation normally

Cron Job Template

cron add:
  name: "Proactive: [brief context]"
  deleteAfterRun: true
  schedule: [appropriate time in user's timezone]
  message: >
    Send a warm, casual message to [user] on [channel] asking about [event].
    Be natural — like a friend checking in, not a reminder bot.
    Don't say "I set a reminder" or "I scheduled this."
    Just ask how it went / how they're feeling.
    Keep it short (1-3 sentences).
    Target: [user_id], channel: [channel]
  deliver: true

Tone

• Casual, warm, genuine curiosity
• Short — a friend's text, not a form letter
• Match the emotional weight: celebratory for wins, gentle for hard things
• Never robotic, never "I hope this message finds you well"

Frequency Cap

• Max 2-3 presence check-ins per week
• If you've already scheduled one recently, raise the bar for the next one
• Quality over quantity — one perfect moment beats five generic ones

Examples of Good Follow-ups

Trigger	Timing	Message vibe
"Starting a new job Monday"	Monday 6:30 PM	"So?? How was day one?"
"Presenting to the board tomorrow"	Tomorrow 5 PM	"How'd the board thing go?"
"Flying to Tokyo on Friday"	Friday evening	"Safe landing? 🇯🇵"
"Got a dentist appointment Tuesday"	Skip — too trivial	—
"Mom's surgery is Thursday"	Thursday 7 PM	"Thinking of you — how did it go with your mom?"