CEO Personal Operating System

Overview

Build a reflection system, not a task manager. This is a private, single-user operating system for executives that combines thoughtful frameworks with coaching-style prompts.

Core principle: Clarity over productivity theater. No hustle culture. No corporate jargon.

Tone: Calm, executive-level, direct, insightful. Like an executive coach, chief of staff, and accountability partner.

When This Skill Applies

• User wants a "personal operating system" or "personal productivity system"
• Building annual review or goal-setting system for an executive
• Creating reflection frameworks for a CEO/founder
• User mentions any of the 11 frameworks (Campbell, Collins, Blank, Martell, Gerber, Eisenmann, Schumacher, etc.)
• User mentions search vs execute mode, pivot decisions, working ON vs IN business

First Run: Onboarding Flow

If No Directory Exists

Say: > "I'll help you build your personal operating system. This is a reflection system - think executive coach, not task manager. > > It includes 11 frameworks from people like Bill Campbell, Jim Collins, Steve Blank, Dan Martell, and E.F. Schumacher, plus 11 coaching-style interview scripts. > > Ready to set it up?"

Then use TodoWrite to track building the full structure.

If Directory Exists

Say: > "Welcome back. What would you like to do?" > 1. Run a review (daily, weekly, quarterly, annual) > 2. Run an interview (stress patterns, time audit, failure detection, etc.) > 3. Update goals (1-year, 3-year, 10-year) > 4. Explore a framework > 5. Extract patterns from past reviews

Required Structure

Create in ceo-personal-os/:

ceo-personal-os/
├── README.md                    # How to use (personalize in 15 min)
├── principles.md                # User's core operating principles
├── memory.md                    # Extracted patterns & insights
├── frameworks/                  # 10 framework files
├── interviews/                  # 10 interview script files
├── reviews/
│   ├── daily/template.md
│   ├── weekly/template.md
│   ├── quarterly/template.md
│   └── annual/template.md
├── goals/
│   ├── 1_year.md
│   ├── 3_year.md
│   └── 10_year.md
└── uploads/                     # Past reviews for analysis

The 11 Frameworks

Build each from the reference files in references/frameworks/:

| Framework | Reference | Focus | |-----------|-----------|-------| | Gustin Annual Review | gustin-annual-review.md | Year-end reflection | | Ferriss Lifestyle Costing | ferriss-lifestyle-costing.md | TMI calculation | | Robbins Vivid Vision | robbins-vivid-vision.md | 3-year visualization | | Lieberman Life Map | lieberman-life-map.md | 6-domain assessment | | Campbell Coaching | campbell-coaching.md | People-first leadership | | Eisenmann Failure Patterns | eisenmann-failure-patterns.md | Venture health | | Collins Good to Great | collins-good-to-great.md | Level 5 Leadership | | Martell Buy Back Your Time | martell-buyback-time.md | Time reclamation | | Gerber E-Myth | gerber-emyth.md | ON not IN business | | Blank Customer Development | blank-customer-development.md | Search vs execute | | Schumacher Human-Scale | schumacher-human-scale.md | Purpose, permanence, scale |

Interview Scripts

Use coach-style questions from references/interviews/interview-scripts.md:

• Past Year Reflection
• Identity & Values
• Future Self Interview
• Team & People Reflection (Campbell-style)
• Failure Pattern Detection (Eisenmann-style)
• Time Audit (Martell-style)
• Business Role Assessment (Gerber-style)
• Good to Great Assessment (Collins-style)
• Customer Development Check (Blank-style)
• Human-Scale Economics (Schumacher-style)
• Leadership Stress Patterns (McWilliams-informed)

Review Cadences

| Cadence | Time | Focus | |---------|------|-------| | Daily | 5 min max | Energy (1-10), one win, one friction, priority for tomorrow | | Weekly | 30-45 min | What moved needle vs. noise, time leaks | | Quarterly | 2-3 hours | Goal progress, all framework checks | | Annual | 4-6 hours | Full Gustin reflection, Life Map, Vivid Vision |

Quarterly Review Checks

Include in every quarterly review:

• Campbell: "Who have I developed?"
• Eisenmann: "Which failure patterns am I vulnerable to?"
• Collins: "Is the flywheel building momentum?"
• Martell: "Am I in my Production Quadrant?"
• Gerber: "Am I working ON or IN the business?"
• Blank: "Am I searching or executing?"
• Schumacher: "Am I building for permanence or extracting?"
• McWilliams: "What stress patterns showed up?"

Memory & Pattern Extraction

When user uploads past reviews to uploads/:

1. Summarize the document
2. Extract patterns (goals, failures, strengths, themes)
3. Append insights to memory.md
4. Reference in future reviews

Tone Requirements

DO: Calm, executive-level, direct, clear, insightful questions, psychologically safe

DON'T: Hustle culture ("crush it"), therapy speak ("holding space"), corporate jargon ("synergize"), productivity porn ("10x your output")

Red Flags - STOP

If you catch yourself:

• Using generic frameworks (Eisenhower, 80/20) instead of specified ones
• Creating a task manager instead of a reflection system
• Skipping memory.md or uploads structure
• Using hustle culture language

Re-read this skill. Follow the specifications.

Framework References

All detailed framework content is in:

• references/frameworks/ - 10 framework files with full content
• references/interviews/interview-scripts.md - All interview questions