The AI-native OKR coach
for startup CEOs

12 Claude Code skills that enforce the cadence that makes OKRs actually work. Not a dashboard. Not a tracker. A coach.

Based on the book Radical Focus by Christina Wodtke

$git clone https://github.com/captainbook/okr-os.git ~/.claude/skills/okr-os && cd ~/.claude/skills/okr-os && ./setup

Requires Claude Code. Zero other dependencies.

The Problem

OKR tools build dashboards.
You need discipline.

The #1 reason OKRs fail isn't bad goals. It's that teams set them and forget them by week 3.

📊

Dashboards don't coach

A chart showing your KR is at 30% doesn't tell you why or what to do about it. You need someone asking the hard questions every Monday.

📋

Tasks masquerade as KRs

"Launch the new dashboard" is a task, not a Key Result. Most teams don't catch this until the quarter is over and no metric moved.

🍎

Golden apples everywhere

New opportunities, customer requests, competitor moves. Every week brings distractions that feel urgent but aren't aligned to your Objective.

How It Works

Three steps. Every quarter.

1

Set up once

Run /okr-setup to define your mission, strategy, and team structure. This creates the foundation every other skill reads from.

2

Set your OKR

Run /okr-set each quarter. The coach guides you through freelist, stack-rank, and selection. ONE Objective. Three Key Results. No exceptions.

3

Run the cadence

/monday for commitments. /friday for wins. Every week, the coach holds you accountable and celebrates progress.

/monday
MONDAY COMMITMENTS — Week 7 of 13 (midpoint) Q2 2026 · Health Score: 72/100 OBJECTIVE: Own the direct-to-business tea market KR1 Revenue $50K/mo 5/10 ▅▅▅▅▅○○○○○ → flat KR2 25 restaurant partners 2/10 ▅▅○○○○○○○○ → DROPPING KR3 NPS > 8 8/10 ▅▅▅▅▅▅▅▅○○ → on track LAST WEEK THIS WEEK ✅ Close Cafe Luna deal P1: Close 3 new leads ✅ Ship supplier dashboard v2 P1: Launch email campaign ❌ Run NPS survey (delayed) P1: Run NPS survey HEALTH ● Customer satisfaction ● Code health ● Morale ⚠️ KR2 confidence dropped 3 points this week. What changed? What can unblock restaurant partnerships?
Features

Opinionated by design

Every feature traces directly to Radical Focus. This is the methodology as code.

ONE Objective hard block

The skill refuses to set more than one company Objective per quarter. No override. No config to change it. Focus is subtraction.

Task-based KR detection

"Launch the dashboard" gets caught and coached into "Dashboard DAU reaches 500." Outcomes, not outputs.

Health Metrics mandatory

Canary metrics that protect what you've built while you stretch. Green, yellow, red. Code Red halts OKR work.

Quarterly timeline awareness

The coach knows it's week 7 of 13 and adjusts its tone. Early weeks are encouraging. Late weeks are urgent.

Cross-quarter learning

After 2+ quarters, the system detects your calibration patterns. Chronic sandbagger? It'll tell you to raise the bar.

Golden Apple detector

Mention a shiny new opportunity mid-quarter? The coach asks: "Does this advance your Objective, or is this Atalanta picking up golden apples?"

Health Score 0-100

One number combining cadence adherence, confidence trajectory, priority completion, and health metric stability.

Shareable artifacts

Every output is designed for copy-paste into Slack or email. Box-drawing for terminal, native formatting for each channel.

All 12 Skills

The complete OKR toolkit

SkillWhat it doesWhen
Phase 1 — Core Cadence
/okr-setupDefine mission, strategy, and prerequisitesOnce, at the start
/okr-setSet quarterly Objective and Key ResultsStart of each quarter
/mondayMonday commitment meeting (Four-Square)Every Monday
/fridayFriday wins celebrationEvery Friday
/okr-coachOn-demand Socratic OKR coachingAnytime
Phase 2 — Reporting & Teams
/okr-statusGenerate weekly status emailWeekly
/okr-teamSet team-level OKRs aligned to companyAfter company OKR
/okr-gradeEnd-of-quarter grading and retrospective2 weeks before quarter ends
/okr-dashboardASCII confidence trends and health scoreAnytime
Phase 3 — Intelligence & Distribution
/okr-introOnboarding one-pager for new team membersWhen someone joins
/okr-syncFormat output for Slack, email, or AttioAfter any cadence skill
/okr-upgradeUpdate OKR-OS to latest versionWhen update available
Why I Built This

From a founder who needed it

I'm Jerome Bajou, CEO and co-founder of Captainbook.io. We've been running OKRs since 2022, and I'm convinced Christina Wodtke's framework played a real part in getting us where we are today.

In just a few years, we put Captainbook on the traveltech map, competing against players with 10x our budget and 50x our headcount. Focus was our edge, and OKRs gave us that focus.

But here's the thing about being early stage: you can't afford an OKR consultant. You can't hire a Chief of Staff to run the process. You just need to move fast and stay pointed in the right direction.

OKR-OS is my answer to that. An AI coach that knows the methodology cold, holds you to the cadence, and catches the mistakes before they cost you a quarter. I built it for myself, and I'm putting it here for anyone who wants the same unfair advantage.

Captainbook
Jerome Bajou
CEO & Co-founder, Captainbook
Get Started

Install in 60 seconds

Requires Claude Code. Zero other dependencies. Works on macOS and Linux.

$git clone https://github.com/captainbook/okr-os.git ~/.claude/skills/okr-os

$cd ~/.claude/skills/okr-os && ./setup
View on GitHub Read Radical Focus