Marketplace ceo-personal-os
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".
git clone https://github.com/aiskillstore/marketplace
T=$(mktemp -d) && git clone --depth=1 https://github.com/aiskillstore/marketplace "$T" && mkdir -p ~/.claude/skills && cp -r "$T/skills/2389-research/ceo-personal-os" ~/.claude/skills/aiskillstore-marketplace-ceo-personal-os && rm -rf "$T"
skills/2389-research/ceo-personal-os/SKILL.mdCEO 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 | | Year-end reflection |
| Ferriss Lifestyle Costing | | TMI calculation |
| Robbins Vivid Vision | | 3-year visualization |
| Lieberman Life Map | | 6-domain assessment |
| Campbell Coaching | | People-first leadership |
| Eisenmann Failure Patterns | | Venture health |
| Collins Good to Great | | Level 5 Leadership |
| Martell Buy Back Your Time | | Time reclamation |
| Gerber E-Myth | | ON not IN business |
| Blank Customer Development | | Search vs execute |
| Schumacher Human-Scale | | 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:
- 10 framework files with full contentreferences/frameworks/
- All interview questionsreferences/interviews/interview-scripts.md