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Claude Skills for Strategy
A strategy that gets done, not one that gets filed.
29 free Claude skills for founders and CEOs. Name the one problem that matters, choose 1–3 bets and what you'll stop doing to pay for them, then turn them into goals, owners and dates your team actually keeps.
Send Me All 29 Strategy SkillsFree. Instant download. No credit card.You've Left the Offsite With Eleven Priorities and Watched the Plan Fade by Spring…
This Time, Your Strategy Gets Done.
From: Michael Barrick
Dear founder,
Most strategies don't die in the planning room. They fade after it.
The offsite ends with a good deck and a long list of priorities. Then the year starts, the urgent work takes over, and by spring nobody can say which three things matter most.
That's not a hunch. Only 28% of the managers who carry out strategy could name three of their company's priorities (MIT Sloan Management Review, 2018).
And the quiet part is the money. In 2006 a Yahoo executive, Brad Garlinghouse, wrote what became known as the Peanut Butter Manifesto: the company spread its money in a thin layer across everything, so it focused on nothing. The Wall Street Journal printed it that November.
It doesn't have to work that way.
I've spent more than ten years studying how boards and companies run, and I built EntityEngine, a company I founded, so a company's mission, projects, tasks and board decisions live in one place instead of in everyone's inbox.
These 29 Claude skills put that thinking to work for you: name the one problem that matters, pick no more than three bets, say what you'll stop doing, and give every piece of work an owner and a date, then keep checking it until it's done.
What Claude Skills for Strategy Are, and How They Work
29 standalone Claude skills that cover strategy from why you exist to the board review. Each skill is a small file you upload once. It teaches Claude to run one strategy job the same careful way every time.
The skills follow seven stages: purpose, diagnosis, bets, goals and measures, initiatives, running it, and the board. Use them in order for a full strategic plan, or pull one skill tonight for your OKRs or next week's board report.
Each skill asks for your facts first, holds you to no more than three bets, marks any missing number as [needs data], gives every action an owner and a date, and checks its own work before you see it. The Plan Your Strategy Route skill picks the right ones for you.
Download all 29 skillsOne zip with one folder per skill, plus a one-page cheat sheet. Free.
What You Can Expect
From Claude Skills for Strategy
The skills follow the order a strategy really gets made and kept: why you exist, what the real problem is, which bets you'll make, how you'll measure them, what work goes behind them, how you run it every week, and how the board oversees it. Every skill also works on its own.
The strategy workflow
Start
Not Sure Where to Begin? Start Here
One skill asks where your strategy stands, your deadline and whether a board is involved, then picks the right skills, runs them in order and checks each step before moving on.
0Plan Your Strategy Route
Skill file: 00-plan-your-strategy-route
Use when
Before an offsite, annual planning or a board retreat, when you don't know where to start
Output
Where your strategy stands, the right skills in order, and each step checked before the next
Skill 00 · Start
If you've ever thought…
“Our offsite is in four weeks and our plan has eleven priorities.”
Send Me All 29 Strategy SkillsStage 1 · 3 skills
Say Why You Exist in Words People Believe
Write a core purpose and mission that would still be true in 50 years, keep only the values that cost you something, and paint a picture of the future concrete enough to check against.
1.1Write Your Core Purpose
Skill file: 01-write-your-core-purpose
Use when
When your mission reads like a slogan, or you're starting a strategic plan
Output
A core purpose and a mission, one line each, tested with the five-whys drill and checked against slogans
Skill 01 · Purpose
If you've ever thought…
“Our mission statement could belong to any company.”
Send Me All 29 Strategy Skills1.2Choose Values That Bite
Skill file: 02-choose-values-that-bite
Use when
When your company values feel generic and nobody acts on them
Output
3–5 core values, each with the behaviours it means and a hiring question
Skill 02 · Purpose
If you've ever thought…
“Integrity, excellence, teamwork. Does anyone actually live these?”
Send Me All 29 Strategy Skills1.3Paint the Vivid Vision
Skill file: 03-paint-the-vivid-vision
Use when
When nobody can picture where you're headed, or before a strategy offsite
Output
A 10-year big goal and a 3-year vivid picture you can check against, flagged if it's only a number
Skill 03 · Purpose
If you've ever thought…
“Our vision is just a revenue number.”
Send Me All 29 Strategy SkillsStage 2 · 4 skills
Name the One Problem That Matters Before Anyone Sets Goals
Build a facts base with a source for every claim, find the crux, mark up the current plan for bad strategy, and see where your money, people and time really go.
2.1Build the Facts Base
Skill file: 04-build-the-facts-base
Use when
Before an offsite or annual planning, when the debate runs on opinions
Output
One page of results, customers, competitors and capabilities, each with a source, fact kept apart from opinion
Skill 04 · Diagnosis
If you've ever thought…
“We argue about the market, but nobody has the facts in one place.”
Send Me All 29 Strategy Skills2.2Find the Crux
Skill file: 05-find-the-crux
Use when
When your strategy is really a target like “grow 20%”
Output
The one challenge that matters most and can be solved, using Rumelt's diagnosis and crux
Skill 05 · Diagnosis
If you've ever thought…
“We have goals. I'm not sure we have a strategy.”
Send Me All 29 Strategy Skills2.3Run the Bad-Strategy Check
Skill file: 06-run-the-bad-strategy-check
Use when
Before an offsite, when you suspect the plan is a wish list
Output
Your plan marked up for fluff, a missing challenge, goals posing as strategy and too many priorities
Skill 06 · Diagnosis
If you've ever thought…
“Is our strategic plan actually a strategy?”
Send Me All 29 Strategy Skills2.4Run the Peanut-Butter Test
Skill file: 07-run-the-peanut-butter-test
Use when
Before budgeting or annual planning, when money is spread across everything
Output
Where money, people and leadership time really go, set against what you say matters, in numbers
Skill 07 · Diagnosis
If you've ever thought…
“We say three things matter, but the budget funds twenty.”
Send Me All 29 Strategy SkillsStage 3 · 5 skills
Choose 1–3 Bets, and What You'll Stop Doing to Pay for Them
Lay out real options, test what would have to be true, run a pre-mortem, pick no more than three bets with a stop list, and write the strategy on one page.
3.1Generate Strategic Options
Skill file: 08-generate-strategic-options
Use when
When the team only argues for one plan
Output
3–5 real options, each a where-to-play and how-to-win choice, including “do less”
Skill 08 · Bets
If you've ever thought…
“Everyone's arguing about the same single plan.”
Send Me All 29 Strategy Skills3.2Test What Would Have to Be True
Skill file: 09-test-what-would-have-to-be-true
Use when
When the strategy debate runs on opinions instead of evidence
Output
What would have to be true for each option, the doubtful conditions, and the cheapest test for each
Skill 09 · Bets
If you've ever thought…
“How do we settle this without just voting on opinions?”
Send Me All 29 Strategy Skills3.3Run a Pre-Mortem
Skill file: 10-run-a-pre-mortem
Use when
Before you commit to bets, a strategic plan or a board vote
Output
Failure stories, ranked risks, early warnings and a fix for each
Skill 10 · Bets
If you've ever thought…
“What could sink this plan that nobody is saying out loud?”
Send Me All 29 Strategy Skills3.4Choose Your Bets and Stop List
Skill file: 11-choose-your-bets-and-stop-list
Use when
After an offsite, or when you have too many priorities
Output
1–3 strategic bets, never more, and a stop list for each
Skill 11 · Bets
If you've ever thought…
“We have eleven priorities. Help.”
Send Me All 29 Strategy Skills3.5Write the One-Page Strategy
Skill file: 12-write-the-one-page-strategy
Use when
For a strategic plan, board approval or an offsite readout
Output
Purpose, diagnosis, guiding policy, 1–3 bets, goals, actions and measures on one page
Skill 12 · Bets
If you've ever thought…
“I need one page everyone can answer to.”
Send Me All 29 Strategy SkillsStage 4 · 4 skills
Turn the Bets Into Goals You Can Measure
Set three-year goals with a baseline and a target, turn each bet into OKRs, find the weekly lead measures, and build one balanced scorecard.
4.1Set Three-Year Goals
Skill file: 13-set-three-year-goals
Use when
When goals are vague or missing, or before annual planning
Output
3–5 outcome goals, each with a baseline, target, date, source and owner
Skill 13 · Goals and measures
If you've ever thought…
“Our goals say “improve” and “grow” but never by how much.”
Send Me All 29 Strategy Skills4.2Turn Bets Into OKRs
Skill file: 14-turn-bets-into-okrs
Use when
For quarterly or annual OKRs and goal-setting
Output
One objective per bet with 3–5 key results, committed vs. stretch, and tasks posing as results caught
Skill 14 · Goals and measures
If you've ever thought…
“Our key results are really just a to-do list.”
Send Me All 29 Strategy Skills4.3Find the Lead Measures
Skill file: 15-find-the-lead-measures
Use when
When your KPIs only tell you, too late, that you missed
Output
1–2 weekly lead measures per goal that your team can move this week
Skill 15 · Goals and measures
If you've ever thought…
“By the time the numbers come in, it's too late to fix anything.”
Send Me All 29 Strategy Skills4.4Build the Strategy Scorecard
Skill file: 16-build-the-strategy-scorecard
Use when
After goals and OKRs are set, when you only track money
Output
One scorecard across money, customers or mission, operations and people, each measure with a baseline, target, source and owner
Skill 16 · Goals and measures
If you've ever thought…
“We track revenue and nothing else.”
Send Me All 29 Strategy SkillsStage 5 · 4 skills
Put the Money, People and Work Behind Each Bet
Turn the bets into a short list of initiatives, move the budget to match, agree targets with the people who own them, and map what each team needs from the others.
5.1Turn Bets Into Initiatives
Skill file: 17-turn-bets-into-initiatives
Use when
When projects don't link to the strategy
Output
3–7 initiatives, each tied to a bet and a goal, with orphan projects put on the stop list
Skill 17 · Initiatives
If you've ever thought…
“Half our projects don't connect to any priority.”
Send Me All 29 Strategy Skills5.2Move the Money
Skill file: 18-move-the-money
Use when
In annual planning or budgeting, before the board approves
Output
A from → to table moving budget, people and time onto the bets, with any bet that has nothing behind it flagged
Skill 18 · Initiatives
If you've ever thought…
“The new budget looks exactly like last year's.”
Send Me All 29 Strategy Skills5.3Run a Catchball Round
Skill file: 19-run-a-catchball-round
Use when
When targets are handed down and the owners don't buy in
Output
Draft targets, the questions owners answer back, and the agreed version on record
Skill 19 · Initiatives
If you've ever thought…
“Our managers nod at the targets and then ignore them.”
Send Me All 29 Strategy Skills5.4Map Cross-Team Commitments
Skill file: 20-map-cross-team-commitments
Use when
When the strategy depends on several departments or sites
Output
A cross-team commitment log: who needs what from whom, by when, with an owner on both sides
Skill 20 · Initiatives
If you've ever thought…
“Work keeps stalling between teams.”
Send Me All 29 Strategy SkillsStage 6 · 5 skills
Keep the Strategy Alive After the Offsite
Give every milestone one owner and a date, check in weekly, review monthly away from the firefighting, check that people can name the priorities, and reset each quarter on the evidence.
6.1Assign Owners and Deadlines
Skill file: 21-assign-owners-and-deadlines
Use when
After annual planning or an offsite, when “the team owns it”
Output
Each initiative split into quarterly priorities and milestones, each with one owner and a due date
Skill 21 · Run it
If you've ever thought…
“Everyone owns it, so nobody does.”
Send Me All 29 Strategy Skills6.2Run the Weekly Check-In
Skill file: 22-run-the-weekly-check-in
Use when
For weekly leadership or team meetings
Output
A 30-minute agenda: last week's commitments, the scoreboard, next week's commitments, plus a commitments log
Skill 22 · Run it
If you've ever thought…
“By March, nobody talks about the plan anymore.”
Send Me All 29 Strategy Skills6.3Run the Monthly Strategy Review
Skill file: 23-run-the-monthly-strategy-review
Use when
For monthly leadership reviews, when firefighting eats the strategy time
Output
A strategy review kept apart from the operations meeting, ending in a review memo
Skill 23 · Run it
If you've ever thought…
“Every strategy meeting turns into a firefighting session.”
Send Me All 29 Strategy Skills6.4Explain the Strategy to Everyone
Skill file: 24-explain-the-strategy-to-everyone
Use when
After setting priorities, to check that people understand them
Output
A plain message for staff, managers, volunteers and the board, plus a “name our 3 priorities” pulse
Skill 24 · Run it
If you've ever thought…
“If I asked our managers to name our three priorities, could they?”
Send Me All 29 Strategy Skills6.5Run the Quarterly Reset
Skill file: 25-run-the-quarterly-reset
Use when
At quarter end, before you set the next quarter's priorities
Output
Keep, change or kill for each bet based on the evidence, with money, people and time moved to match
Skill 25 · Run it
If you've ever thought…
“The plan doesn't fit anymore, but we keep defending it.”
Send Me All 29 Strategy SkillsStage 7 · 3 skills
Give the Board Its Real Job: Test, Approve and Watch
Prepare the board strategy session with the options turned down, report progress on one page each quarter, and give directors oversight questions that don't drift into managing.
7.1Prepare the Board Strategy Session
Skill file: 26-prepare-the-board-strategy-session
Use when
Before a board retreat or a board strategy meeting
Output
A board pack: the one-page strategy, the options turned down and why, the key risks, and the decision you're asking for
Skill 26 · Board
If you've ever thought…
“The board is reviewing our strategy next month.”
Send Me All 29 Strategy Skills7.2Build the Board Strategy Report
Skill file: 27-build-the-board-strategy-report
Use when
Before a quarterly board meeting
Output
A one-page board report: red items first, each bet's scorecard, the risks and the decisions needed
Skill 27 · Board
If you've ever thought…
“Our board report is forty pages of updates.”
Send Me All 29 Strategy Skills7.3Ask the Board Oversight Questions
Skill file: 28-ask-the-board-oversight-questions
Use when
Before a board meeting, retreat or strategy review, if you're a director
Output
Oversight questions for each stage, rewrites for questions that drift into managing, and a nonprofit lens
Skill 28 · Board
If you've ever thought…
“What should I ask about the strategy without managing it?”
Send Me All 29 Strategy SkillsWhich Claude Skill Fits Your Strategy Question?
Match the question you're asking right now to the skill built for it. Each row is colored by the stage it belongs to.
Set Up Claude Skills for Strategy in 5 Minutes
- Download the skills pack.One zip with all 29 skills, one folder per skill, plus the cheat sheet. Keep the whole set or pull out only the stage you're working on.
- Turn on code execution in Claude.In claude.ai, open Settings → Capabilities and switch on code execution and file creation. On Team and Enterprise plans, your admin controls this.
- Upload the skills.Go to Customize → Skills, click +, then Create skill → Upload a skill. Start with 00-plan-your-strategy-route, then add as many as you like. Using ChatGPT or another AI? Paste a skill's text into the chat instead.
- Ask in plain words.Attach your plan, notes or numbers and say what you need. Claude applies the skill's method and shows where every finding came from.
The Quality Bar Every Strategy Skill Meets
Every skill pushes Claude toward a strategy that holds up when your team, your board or your own numbers test it, not generic AI filler.
Questions Leaders Ask About Claude Skills for Strategy
What does this pack help me do?
It helps you set a strategy and then carry it out: write a purpose people believe, name the one problem that matters, choose 1–3 bets and a stop list, turn them into goals, measures and initiatives with owners and dates, run the weekly, monthly and quarterly rhythm, and report to your board.
Do I have to use all 29 skills?
No. Each skill stands on its own. Run them in order for a full strategic plan, or pull one when you only need OKRs, a scorecard or the board report.
Does it work for nonprofits?
Yes. One of the two worked examples is a nonprofit with a volunteer board, and the board skills include a nonprofit lens.
Don't most strategies fail anyway?
You've probably seen a big “strategies fail” percentage. Those famous figures don't trace back to solid studies, and an academic review found nobody knows the real rate, so we don't use them. What the research does show is that most leaders struggle to carry strategy out, and the skills are built around the reasons why.
How do the skills get into Claude?
Each skill is one folder with a single file. Upload the ones you need in Customize → Skills, then ask in plain words or name the skill in your prompt.
Do I need a paid Claude plan?
No. Skills work on Claude's free plan. Long jobs, like a full strategic plan with many files, run more smoothly on a paid plan.
Is it safe to use with our real strategy papers?
Only in an AI tool your company has approved. Strategy papers are some of the most sensitive documents a company has, and every skill reminds you of that.
Is this a replacement for a strategy consultant?
No. It does the structured thinking and the paperwork fast. The choices are still yours and your team's.
How does this connect to EntityEngine?
Claude helps you set the strategy. EntityEngine is where you run it: adopt your mission, vision and values by board ballot, run each bet as a project with its own key results and check-ins, and give every task an owner and a due date.
Is this legal or financial advice?
No. It's general education, not legal, tax, accounting or financial advice.
Set It With Claude, Then Run It in EntityEngine
A strategy gets done when the work behind it lives somewhere your team looks every day. Keep the mission, the projects, the tasks and the board record in one place.
How they fit together
What EntityEngine does for you today
Set a Strategy That Gets Done
Your team doesn't need a longer plan. It needs one problem named, 1–3 bets chosen, and an owner and a date on every piece of work.
EntityEngine is a company Michael Barrick founded. Claude is a product of Anthropic; Claude Skills for Strategy is not made or endorsed by Anthropic. The Yahoo memo was printed by The Wall Street Journal on 18 November 2006. General education, not legal, tax, accounting or financial advice. The presenter in this video is an AI version of Michael Barrick.