name

ceo-personal-os

description

This skill should be used when building a personal productivity or operating system for a CEO, founder, or executive. Triggers on "personal OS", "annual review", "life planning", "goal setting system", "Bill Campbell", "Trillion Dollar Coach", "startup failure patterns", "Good to Great", "Level 5 Leadership", "Buy Back Your Time", "E-Myth", "Customer Development", "Steve Blank", "Small Is Beautiful", "Schumacher", "human-scale", "subsidiarity", "Buddhist economics", "permanence".

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?"

Run a review (daily, weekly, quarterly, annual)

Run an interview (stress patterns, time audit, failure detection, etc.)

Update goals (1-year, 3-year, 10-year)

Explore a framework

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/:

Summarize the document
Extract patterns (goals, failures, strengths, themes)
Append insights to memory.md
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