# Proactive Messages

> 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.

- Skill: `modbender/proactive-messages` (Agent Skill)
- Install (CLI): `npx skillmds@latest add modbender/proactive-messages`
- Raw SKILL.md: https://api.skillmd.com/api/skills/modbender/proactive-messages/raw
- Safety review: pending (external: skill-scanner FAIL, skillspector PASS)
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Productivity
- Author: modbender (https://skillmd.com/u/modbender)
- Updated: 2026-09-09
- Page: https://skillmd.com/skills/modbender/proactive-messages

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# 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?" |