Strategy OS

Name: strategy-os
Author: josephfung

Strategy OS turns scattered strategy artifacts into a single, testable, executable system.

Three operating modes for Claude — a lifecycle for building strategy, a passive analyst that flags drift, and a coach that tracks your KPIs over time.

Mode	Type	What it does
Strategy Lifecycle	Skill (episodic)	5-phase workflow: consolidate, stress-test, communicate, compile, govern
Strategy Analyst	Subagent (ambient)	Watches your conversations passively, flags potential misalignments with the strategy. Advisory, never directive.
Strategy Coach	Subagent (scheduled)	KPI tracking and accountability partner. Runs setup interview, periodic check-ins, and builds an execution narrative over time.

All three modes share a data layer at ~/.claude/strategy-os/data/ — the same location in both Claude Code and Claude Desktop.

Without Strategy OS

"Pull my strategy together" gets you generic advice about alignment frameworks
"Stress-test this before my board meeting" returns a list of open-ended questions
Nothing connects back to your actual documents — you get theory, not a working memo
Every claim looks the same — you can't tell what came from your docs vs. what the AI inferred
"Set up drift detection" gets you a suggestion to have a weekly meeting

With Strategy OS

Phase	Mode	What it does
Consolidate	Strategy architect	Inventory your artifacts, extract every claim into a table, label each Explicit / Inferred / Unknown, and draft a canonical Strategy Consolidation Memo.
Stress-test	Adversarial reviewer	Run a pre-mortem, bull/bear case, constraint shock, or synthetic stakeholder panel. Every finding becomes a specific memo edit, not a vague concern.
Communicate	Comms strategist	Lock the strategy objects, then translate into board memo, all-hands story, exec alignment note, sales enablement, or CEO narrative — without drifting from the source.
Compile	Work architect	Map the memo to Objective → Pillars → Bets → Epics → Tickets with hypothesis-driven definitions of done and traceability tags.
Govern	Ops monitor	Weekly drift detection, monthly pillar reviews, quarterly planning packets, and agent guardrails for safe AI-assisted execution.

Alongside the lifecycle, the Strategy Analyst watches every conversation. If you start talking about hiring, roadmap changes, or resource allocation in a way that cuts against your stated strategy, it surfaces a note before you proceed. You can dismiss it, log it, or update your strategy — but it never blocks work.

The Strategy Coach sets up a KPI registry in a brief interview, then checks in at whatever cadence you choose (weekly, monthly, or a mix per KPI). Each check-in logs the current value and builds a running narrative of execution health over time.

Strategy OS Demo

You:    I have a board deck, product roadmap, sales pitch, and OKRs
        that all say different things. Help me get my strategy together.

Claude: [Runs the 18-question intake interview, builds extraction table]
        Found 23 explicit claims, 8 inferred patterns, 4 unknowns.
        3 contradictions flagged. Here's your strategy skeleton for approval...

You:    Looks good. Now stress-test it — board meeting is Tuesday.

Claude: [Pre-mortem: 10 failure modes with provenance labels]
        [Synthetic stakeholder panel: simulates 5 board reviewers]
        Two critical issues: your growth bet contradicts your burn target,
        and Pillar 3 has no owner. Recommended memo edits attached.

You:    Fix those and generate my board materials.

Claude: [Locks 4 strategy objects, applies stakeholder reframing matrix]
        Board memo, all-hands narrative, and exec alignment note ready.
        All trace back to the approved memo — zero drift.

You:    Now turn it into work I can assign.

Claude: [Maps memo to 3 pillars → 7 bets → 14 epics → 42 tickets]
        Each ticket has a traceability tag (P1-B2-E3), hypothesis,
        and definition of done. Ready for Jira/Monday/ClickUp import.

You:    We've been executing for 6 weeks. Are we drifting?

Claude: [Scans active work against the memo]
        Enterprise SSO work violates your "PLG-first" trade-off.
        Pillar 2 has zero ticket activity in 3 weeks.
        Recommended: reassign SSO to P3-B1, escalate Pillar 2 stall.

[Later, during an unrelated conversation]

Strategy Analyst: ⚑ Strategic signal detected (cluster: resources)
        You mentioned hiring 3 engineers for the data platform. Your
        strategy memo designates the data platform as a Pillar 3 bet —
        lower priority than Pillar 1 growth work. Flag for awareness.
        [Dismiss] [Log it] [Update strategy]

[At session start, one week later]

Strategy Coach:   KPI check-in is overdue (7 days since last check-in).
        Last week: ARR $1.2M, churn 2.1%, NPS 41.
        What are your numbers this week?

Before & after screenshots

These show the same prompt sent to Claude with and without Strategy OS installed.

Who this is for

You're a startup or scaleup CEO who already has strategy artifacts everywhere — board decks, OKR docs, roadmaps, investor updates — and none of them say the same thing. You want a system that turns that mess into a single source of truth, pressure-tests it, and keeps execution aligned to it over time.

This is not a strategy course. It's an operating system for CEOs who already know their business and need a structured way to get it out of their head and into their organization.

Install

Claude Code — full installation (recommended)

Installs all three modes: lifecycle, ambient analyst, and coach with automatic cadence checking.

claude plugin marketplace add josephfung/strategy-os
claude plugin install strategy-os

The plugin registers the @strategy-analyst and @strategy-coach subagents and wires the hooks that make ambient detection and coach cadence checking work automatically on every session.

Other agents — Cursor, Codex, and 37+ others

Installs the /strategy lifecycle skill. The analyst and coach are available via explicit invocation but ambient hooks are not supported outside Claude Code.

npx skills add josephfung/strategy-os

Cowork

Download strategy-os.plugin from the latest release, then upload it in Cowork via Customize → Browse plugins → Upload.

MCP connections (optional)

The skill works standalone with uploaded files. It gets more powerful with tool connections:

Jira / Monday.com / ClickUp — Query existing tickets for drift detection, propose new epics with pillar tags, generate cadence reports from live project data.
Google Drive / Dropbox — Scan for strategy artifacts during the inventory phase.
Slack — Post weekly drift summaries to a designated channel.

How I use this skill

Created by Joseph Fung.

I built Strategy OS because I kept watching CEOs — myself included — treat strategy as a one-time document instead of a living system. You write the memo, present to the board, and then execution slowly drifts until the next planning cycle forces a reset.

Consolidation is not stress-testing. Stress-testing is not communication. Communication is not execution. If you blur them together, you get a deck that sounds good but doesn't survive contact with reality.

I want explicit phases. Each one has a job, produces a specific artifact, and hands off cleanly to the next. That's the unlock.

The analyst and coach extend that discipline into ongoing execution — not just during the planning cycle, but in every conversation and every week.

Also available: Strategy OS Downloadable Pack

If you're not using Claude, the framework is available as 16 standalone markdown files with copy-paste prompts that work with any AI tool. See the article at josephfung.ca/strategy-os-bf2d7294d608.

strategy-os