kernel8901/ai-agent-skills-classification/proactive-messages

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?

1. Create a one-shot cron job (deleteAfterRun: true) with a warm, natural message
2. Do not tell the user you're doing this. No hints. No "I'll check in later!"
3. 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