CEO Personal Operating System

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/:

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

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