Agent skill

strategic-compact

Suggests manual context compaction at logical intervals to preserve context through task phases rather than arbitrary auto-compaction.

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Install this agent skill to your Project

npx add-skill https://github.com/oldwinter/skills/tree/main/lenny-skills/leadership-skills/strategic-compact

SKILL.md

Strategic Compact Skill

Suggests manual /compact at strategic points in your workflow rather than relying on arbitrary auto-compaction.

Why Strategic Compaction?

Auto-compaction triggers at arbitrary points:

  • Often mid-task, losing important context
  • No awareness of logical task boundaries
  • Can interrupt complex multi-step operations

Strategic compaction at logical boundaries:

  • After exploration, before execution - Compact research context, keep implementation plan
  • After completing a milestone - Fresh start for next phase
  • Before major context shifts - Clear exploration context before different task

How It Works

The suggest-compact.sh script runs on PreToolUse (Edit/Write) and:

  1. Tracks tool calls - Counts tool invocations in session
  2. Threshold detection - Suggests at configurable threshold (default: 50 calls)
  3. Periodic reminders - Reminds every 25 calls after threshold

Hook Setup

Add to your ~/.claude/settings.json:

json
{
  "hooks": {
    "PreToolUse": [{
      "matcher": "tool == \"Edit\" || tool == \"Write\"",
      "hooks": [{
        "type": "command",
        "command": "~/.claude/skills/strategic-compact/suggest-compact.sh"
      }]
    }]
  }
}

Configuration

Environment variables:

  • COMPACT_THRESHOLD - Tool calls before first suggestion (default: 50)

Best Practices

  1. Compact after planning - Once plan is finalized, compact to start fresh
  2. Compact after debugging - Clear error-resolution context before continuing
  3. Don't compact mid-implementation - Preserve context for related changes
  4. Read the suggestion - The hook tells you when, you decide if

Related

  • The Longform Guide - Token optimization section
  • Memory persistence hooks - For state that survives compaction

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