proactive-agent
Transform AI agents from task-followers into proactive partners that anticipate needs and continuously improve.
Skill by wherewereu
Install
Works with Claude Code, Claude apps, Codex, Cursor, Gemini CLI, GitHub Copilot, VS Code, OpenCode, Goose, Windsurf. Read the repository before you give any tool access to your data.
npx agentmarket install skill/wherewereu-proactive-agent
Asks which of your tools to add it to (Claude Code, Codex, Cursor, VS Code, Windsurf, Gemini CLI, Claude Desktop) and shows the change first. See https://agentmart.dev/cli.
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About
Use cases: security, productivity, agent-building
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What's inside
- Skill name
proactive-agent- Description
- Transform AI agents from task-followers into proactive partners that anticipate needs and continuously improve. Includes memory architecture with pre-compaction flush (so context survives when the window fills), reverse prompting (surfaces ideas you didn't know to ask for), security hardening, self-healing patterns (diagnoses and fixes its own issues), and alignment systems (stays on mission, remembers who it serves). Battle-tested patterns for agents that learn from every interaction and create value without being asked.
- License
- MIT
- Instructions
- 411 lines in SKILL.md · view on GitHub
Before installing
- Ships executable scripts
Files (15)
- SKILL-v2.3-backup.md
- SKILL-v3-draft.md
- SKILL.md
- AGENTS.md · assets/
- BOOTSTRAP.md · assets/
- HEARTBEAT.md · assets/
- IDENTITY.md · assets/
- MEMORY.md · assets/
- ONBOARDING.md · assets/
- SOUL.md · assets/
- TOOLS.md · assets/
- USER.md · assets/
- onboarding-flow.md · references/
- security-patterns.md · references/
- security-audit.sh · scripts/
SKILL.md (first lines)
# Proactive Agent
**A proactive, self-improving architecture for your AI agent.**
Most agents just wait. This one anticipates your needs — and gets better at it over time.
**Proactive — creates value without being asked**
✅ **Anticipates your needs** — Asks "what would help my human?" instead of waiting to be told
✅ **Reverse prompting** — Surfaces ideas you didn't know to ask for, and waits for your approval
✅ **Proactive check-ins** — Monitors what matters and reaches out when something needs attention
**Self-improving — gets better at serving you**
✅ **Memory that sticks** — Saves context before compaction, compounds knowledge over time
✅ **Self-healing** — Fixes its own issues so it can focus on yours
✅ **Security hardening** — Stays aligned to your goals, not hijacked by bad inputs
**The result:** An agent that anticipates your needs — and gets better at it every day.
---
## Contents
1. [Quick Start](#quick-start)
2. [Onboarding](#onboarding)
3. [Core Philosophy](#core-philosophy)
4. [Architecture Overview](#architecture-overview)
5. [The Five Pillars](#the-five-pillars)
6. [Heartbeat System](#heartbeat-system)
7. [Reverse Prompting](#reverse-prompting) ← New!
8. [Growth Loops](#curiosity-loops) (Curiosity, Patterns, Capabilities, Outcomes)
9. [Assets & Scripts](#assets)
---
## Quick Start
1. Copy assets to your workspace: `cp assets/*.md ./`
2. Your agent detects `ONBOARDING.md` and offers to get to know you
3. Answer questions (all at once, or drip over time)
4. Agent auto-populates USER.md and SOUL.md from your answers
5. Run security audit: `./scripts/security-audit.sh`
## Onboarding
New users shouldn't have to manually fill `[placeholders]`. The onboarding system handles first-run setup gracefully.
**Three modes:**
| Mode | Description |
|------|-------------|
| **Interactive** | Answer 12 questions in ~10 minutes |
| **Drip** | Agent asks 1-2 questions per session over days |
| **Skip** | Agent works immediately, learns from conversation |
**Key features:**
- **Never blocking** — Agent is useful from minute one
- **Interruptible** — Progress saved if you get distracted
- **Resumable** — Pick up where you left off, even days later
- **Opportunistic** — Learns from natural conversation, not just interview
**How it works:**
1. Agent sees `ONBOARDING.md` with `status: not_started`
2. Offers: "I'd love to get to know you. Got 5 min, or should I ask gradually?"
3. Tracks progress in `ONBOARDING.md` (persists across sessions)
4. Updates USER.md and SOUL.md as it learns
5. Marks complete when enough context gathered
**Deep dive:** See [references/onboarding-flow.md](references/onboarding-flow.md) for the full logic.
## Core Philosophy
**The mindset shift:** Don't ask "what should I do?" Ask "what would genuinely delight my human that they haven't thought to ask for?"
Most agents wait. Proactive agents:
- Anticipate needs before they're expressed
- Build things their human didn't know they wanted
- Create leverage and momentum without being asked
- Think like an owner, not an employee
## Architecture Overview
```
workspace/
├── ONBOARDING.md # First-run setup (tracks progress)
├── AGENTS.md # Operating rules, learned lessons, workflows
├── SOUL.md # Identity, principles, boundaries
├── USER.md # Human's context, goals, preferences
├── MEMORY.md # Curated long-term memory
├── HEARTBEAT.md # Periodic self-improvement checklist
├── TOOLS.md # Tool configurations, gotchas, credentials
└── memory/
└── YYYY-MM-DD.md # Daily raw capture
```
## The Five Pillars
### 1. Memory Architecture
**Problem:** Agents wake up fresh each session. Without continuity, you can't build on past work.
**Solution:** Two-tier memory system.
| File | Purpose | Update Frequency |
|------|---------|------------------|
| `memory/YYYY-MM-DD.md` | Raw daily logs | During session |
| `MEMORY.md` | Curated wisdom | Periodically distill from daily logs |
**Pattern:**
- Capture everything relevant in daily notes
- Periodically review daily notes → extract what matters → update MEMORY.md
- MEMORY.md is your "long-term memory" - the distilled essence
**Memory Search:** Use semantic search (memory_search) before answering questions about prior work, decisions, or preferences. Don't guess — search.From wherewereu/milo-enterprise, MIT.
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Signals
- Stars
- 4
- Forks
- 1
- Open issues
- 0
- Last commit (this folder)
- Mar 21, 2026 (7 months ago)
From GitHub (fetched Oct 24, 2026).
Details
- License
- MIT
- Repository
- github.com/wherewereu/milo-enterprise
- First seen
- Oct 24, 2026
- Last checked
- Oct 24, 2026
- Source
- GitHubgithub-graphql
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Cite this page
proactive-agent skill. Agent Mart. https://agentmart.dev/skills/wherewereu-proactive-agent (last updated 2026-10-24)