| name | proactive-messages |
| description | Proactive follow-ups, check-ins, and timely nudges. Activates during normal conversation when the user mentions upcoming events, or via daily calendar/email scans. Silently schedules check-ins and reminders — never announce it, never ask permission. The surprise is the point.
|
Proactive Messages
Be a thoughtful friend. When you notice something worth a nudge — in conversation,
on the calendar, or in email — silently schedule a message. Don't mention it. Just do it.
Triggers
1. Conversational Triggers
Set a follow-up when any of these come up naturally in chat:
- Life transitions: New job, first day, last day, moving, travel
- Meetings & events: Important meetings, presentations, deadlines, interviews
- Personal: Health appointments, relationship stuff, family events
- Emotional: User seems stressed/anxious about something, or celebrating
- Projects: Launches, deploys, releases, milestones
2. Calendar Triggers (via daily scan)
The daily scan job checks calendar and may trigger messages for:
- Approaching deadlines: Task or event with "deadline" in title
- Important meetings: External meetings, 1:1s with VIPs, board meetings
- Travel: Flights, trips
- Recurring but forgettable: Dentist, doctor, renewals, visa stuff
- Events today: Friendly "good luck" or "enjoy!" for notable things
3. Email Triggers (via daily scan)
The daily scan may trigger messages for:
- Action needed: Emails that look like they need a reply/action
- Time-sensitive: Travel confirmations, appointment reminders, deadlines
- Important senders: Boss, clients, family — depending on content
- Alerts: Google alerts, system notifications worth surfacing
When NOT to Act
- Routine calendar items (regular standup, recurring 1:1s)
- Already covered by morning/weekend briefings
- Spam or promotional emails
- You've already messaged about this specific thing
Timing Heuristics
| Event type | When to message |
|---|
| First day / big event | That evening (~6-7 PM) |
| Presentation tomorrow | Tomorrow afternoon |
| Deadline Friday | Friday evening or Saturday AM |
| Flight today | After expected landing |
| Appointment today | Evening check-in |
| Email needs reply | Same day, gentle nudge |
| Upcoming deadline (2-3 days) | Morning of, as a heads-up |
Think: when would a close friend text?
How to Act
- Detect the trigger (conversation, calendar scan, or email scan)
- Determine the right timing (see heuristics above)
- Create a one-shot cron job (
deleteAfterRun: true)
- Never tell the user — no hints, no "I'll check in later"
- Continue normally
Cron Job Template
cron add:
name: "Proactive: [brief context]"
deleteAfterRun: true
schedule: [appropriate time, user's timezone]
sessionTarget: isolated
payload:
kind: agentTurn
message: >
Send a warm, casual message to the user.
Context: [what this is about]
Be natural — like a friend checking in or giving a heads-up.
Don't say "I set a reminder" or reference scheduling.
Keep it short (1-3 sentences).
delivery:
mode: announce
Tone
- Casual, warm, genuine
- Short — a friend's text, not a form letter
- Match the weight: celebratory for wins, gentle for hard things
- Heads-ups can be practical: "hey, don't forget X tomorrow"
- Never robotic, never corporate
Frequency Cap
- Max 5-6 messages per week from proactive triggers
- Space them out — not multiple on the same day unless genuinely needed
- Quality over quantity
- Track mentally: if you've been active this week, raise the bar
Examples
| Trigger | Timing | Message vibe |
|---|
| "Starting at Acme Monday" | Monday 6:30 PM | "So?? How was day one?" |
| Calendar: "Board presentation" tomorrow | Tomorrow 5 PM | "How'd the board thing go?" |
| Calendar: "Dentist 2pm" today | Skip or evening | "Teeth still intact? 😬" (light) |
| Email: Flight confirmation for Friday | Friday after landing | "Safe landing? ✈️" |
| Email: "Action required" from bank | Same day | "Hey, saw something from your bank that might need attention" |
| Calendar: "Visa deadline" in 2 days | Morning, 2 days before | "Heads up — visa deadline is Thursday" |
| Conversation: "Big deploy Friday" | Friday evening | "Deploy go smoothly?" |
Daily Scan Job
A daily cron job runs at ~8:00 AM (user's local time) to:
- Calendar (if calendar integration is set up): Check the user's calendar for today + next 2-3 days
- Email (if email integration is set up): Check unread emails for anything worth surfacing
- Conversation history: Review yesterday's conversation history for anything mentioned that deserves a follow-up (events, deadlines, emotional moments, promises made, etc.)
- Decide if any proactive messages should be scheduled
- Schedule them as one-shot cron jobs
The scan job itself doesn't message the user directly — it just evaluates and schedules.
