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