proactive-messages_skill

Overview

This skill silently schedules thoughtful follow-ups and check-ins when the user mentions significant life moments during normal conversation. It behaves like a considerate friend: detecting important events, setting a one-shot follow-up, and sending a warm, short message at an appropriate future time. The follow-ups are never announced or requested — the surprise is intentional. Frequency is limited to avoid over-messaging.

How this skill works

During conversation the skill detects mentions of non-routine, consequential events (new jobs, big meetings, travel, health or relationship milestones, deadlines, interviews, etc.). It chooses a human-friendly follow-up time based on the event and user timezone, then creates a one-shot scheduled job that will deliver a short, natural check-in message. The scheduling is silent: the user is not informed that a follow-up was created, and the job deletes itself after running.

When to use it

• Life transitions: new job, moving, first/last day, long travel
• High-stakes moments: presentations, interviews, important meetings, deadlines
• Personal or emotional events: surgeries, health appointments, relationship milestones, bereavement
• Major projects and launches where outcomes matter
• When the user expresses stress, anxiety, or celebration about an upcoming event

Best practices

• Only act on non-routine, meaningful events — skip trivial or daily matters
• Pick timing like a close friend would: evening after a first day, afternoon after a presentation
• Keep messages short (1–3 sentences) and emotionally appropriate — celebratory for wins, gentle for hard news
• Limit follow-ups to 2–3 presence check-ins per week to avoid fatigue
• Use natural language; never state that a reminder was set or that scheduling occurred

Example use cases

• User says "Starting a new job Monday" → schedule Monday evening: "So?? How was day one?"
• User mentions "Big presentation tomorrow" → schedule tomorrow afternoon: "How'd the presentation go?"
• User shares "Flying to Tokyo on Friday" → schedule Friday night: "Safe landing? How's Tokyo?"
• User reports "Mom's surgery is Thursday" → schedule Thursday evening: "Thinking of you — how did it go with your mom?"
• User notes a major launch next week → schedule post-launch check-in to ask how it went and how they’re feeling