HomeSkillsSkills for StrategyAndrew PershJuly 5, 202612 min read

50 agents. 150 prompts. 30 plug-and-play skills.

Run a Full Strategy Engagement on Fable 5 Instead of a Retainer

30 plug-and-play Claude skills, with 150 example prompts, that run a full strategy engagement as a roughly 50-agent workflow across 5 phases: diagnose the question, map the market, choose the path, build the roadmap, and write the memo. Download the pack and run the engagement yourself.

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Run a full strategy engagement on Fable 5 instead of a retainer

Run a full strategy engagement on Fable 5 instead of a retainer, and the usual six-figure scope of work collapses into 30 focused Claude skills you run yourself. They cover the 5 phases of a real engagement: diagnose the question, map the market, choose the path, build the roadmap, and communicate the decision. Each skill is a single markdown file that teaches Claude a named, repeatable method instead of a vague instruction to do some strategy work, and each ships with example prompts.

This is the shape of a real strategy engagement, condensed. The 30 skills carry 150 example prompts between them, and running the whole thing end to end is roughly a 50-agent workflow: each skill spins up its own focused Claude session, and each phase is synthesized before it feeds the next. Teams that used to bring in outside help for a full-scope review are increasingly running the same 5 phases themselves, with Claude doing the framing, the market read, the option comparison, and the first draft of every deliverable. You still own every decision the skills inform. The skills remove the hours it used to take to reach the point where a decision was possible.

For the fuller six-domain operating system this pack sits inside, see our Strategy Skills for Claude Fable 5, and for a lighter set built for a standing weekly cadence, see our 9 Claude Workflows for Strategy.

Download all 30 skills

One zip, one folder per skill, 5 phases. Free, no signup.

Download the zip

The 30 skills behind the engagement

5 phases, 30 skills, 6 in each phase. Every one is a standalone SKILL.md file that teaches Claude a named method for one specific part of a strategy engagement, not a generic prompt to analyze something. Between them the skills carry 150 example prompts, and running the full engagement is roughly a 50-agent workflow. Install every phase, or pull out just the skill you need.

The five-phase strategy engagement

Phase 1 of 5 · Diagnose · 6 skills
1

Diagnose

Frame the question and read the current state before anyone builds a slide. Turn a vague executive worry into one testable question, a MECE issue tree, an early hypothesis set, and a time-boxed workplan.

Problem Framing

Turn a vague executive concern into one sharp, testable strategic question with a clear decision owner

Skill file: problem-framing

Situation Assessment

Build a fast current-state picture of the business, its performance, and the forces pressing on it

Skill file: situation-assessment

Stakeholder Mapping

Map who decides, who influences, and who blocks, then plan how to win each of them

Skill file: stakeholder-mapping

Issue Tree Builder

Decompose the core question into a MECE issue tree of sub-questions you can actually answer

Skill file: issue-tree-builder

Hypothesis Generation

Draft an early answer-first hypothesis set so the engagement chases evidence, not everything

Skill file: hypothesis-generation

Workplan Design

Convert the issue tree into a time-boxed analysis plan with owners, methods, and deliverables

Skill file: workplan-design

Phase 2 of 5 · Map · 6 skills
2

Map

Build the evidence base. Decide what data is decision-grade, size the market two ways, profile the competition, cut the customer base into real segments, and turn raw interviews into ranked findings.

Data Gathering Plan

Decide exactly what data you need, where to get it, and how to make it decision-grade

Skill file: data-gathering-plan

Market Sizing

Size the market top-down and bottom-up with transparent assumptions and a sanity-checked range

Skill file: market-sizing

Competitor Mapping

Profile the competitive field, positioning, and moves to find where the white space is

Skill file: competitor-mapping

Customer Segmentation

Cut the customer base into segments that differ in needs, value, and how to serve them

Skill file: customer-segmentation

Interview Synthesis

Turn raw interview and call notes into ranked, evidence-backed findings and quotes

Skill file: interview-synthesis

Value Chain Analysis

Map the value chain and cost-to-serve to expose where margin and leverage really sit

Skill file: value-chain-analysis

Phase 3 of 5 · Choose · 6 skills
3

Choose

Force a real decision. Generate genuinely distinct options, model the scenarios and the economics of each, score them against weighted criteria, and compress everything into one defensible recommendation.

Option Generation

Generate a genuinely distinct set of strategic options, not three flavors of the same idea

Skill file: option-generation

Scenario Modeling

Build base, upside, and downside scenarios with named drivers and tipping points

Skill file: scenario-modeling

Financial Modeling

Model the P and L, cash, and returns of each option so the numbers can be compared

Skill file: financial-modeling

Prioritization Scoring

Score options against weighted criteria to force a defensible, transparent ranking

Skill file: prioritization-scoring

Business Case Builder

Assemble the recommended option into a full business case a board can actually approve

Skill file: business-case-builder

Recommendation Synthesis

Compress all the analysis into one clear recommendation with the reasoning behind it

Skill file: recommendation-synthesis

Phase 4 of 5 · Execute · 6 skills
4

Execute

Turn the choice into a plan that survives the calendar. Sequence the roadmap, design the operating model, charter each initiative, surface the risks, define the KPIs, and plan the people side of the change.

Roadmap Design

Sequence the chosen strategy into phased workstreams, milestones, and dependencies

Skill file: roadmap-design

Operating Model Design

Design the org, roles, and decision rights needed to actually run the new strategy

Skill file: operating-model-design

Initiative Charter

Charter each major initiative with scope, owner, success metrics, and resourcing

Skill file: initiative-charter

Risk Assessment

Surface the risks that could sink the plan and pair each with a concrete mitigation

Skill file: risk-assessment

KPI Dashboard Design

Define the leading and lagging KPIs and the dashboard that tracks whether it is working

Skill file: kpi-dashboard-design

Change Management Plan

Plan the people side of the change so the strategy lands instead of stalling

Skill file: change-management-plan

Phase 5 of 5 · Communicate · 6 skills
5

Communicate

Make the recommendation survive the room. Write the answer-first summary and board memo, build the slide narrative, draft the slides, pre-empt the hard questions, and run the decision meeting to a commitment.

Executive Summary

Write the one-page answer-first summary a busy executive reads before anything else

Skill file: executive-summary

Board Memo

Draft the board-ready memo that frames the decision, options, and the ask

Skill file: board-memo

Presentation Narrative

Build the storyline and slide flow that carries an audience from problem to decision

Skill file: presentation-narrative

Slide Drafting

Turn each storyline point into a single-message slide with a real action title

Skill file: slide-drafting

Objection Handling

Pre-empt the hardest questions and rehearse crisp, evidence-backed answers

Skill file: objection-handling

Readout Facilitation

Plan and run the decision meeting so the room leaves aligned on a commitment

Skill file: readout-facilitation

Setup guide

Step 1

Download the skills pack

Download all 30 skills (.zip)

The zip contains all 30 skills, grouped into 5 phases, each a single SKILL.md file. Unzip it anywhere. Keep the whole engagement, or pull out just the skill you need.

Step 2

Create a Claude Project

Go to claude.ai, open the left sidebar, click Projects, then Create Project. Name it something like "Strategy Engagement" so you can reuse it for every project.

Claude Projects view with the New project button highlighted
Step 3

Add the skills as Project Knowledge

Inside your project, open Project Knowledge, click Add Content, and upload the .md files. Add one phase or all 30 skills. Claude will reference them automatically in every conversation inside that project.

Finder window with the skill markdown files being dragged into the Claude project Files panel
Step 4

Run the phases in sequence

Open a new conversation inside the project, paste in your data, and name the skill you want Claude to run. Chain skills in one session: the market-sizing output can feed directly into option-generation and then financial-modeling.

Claude conversation using a strategy skill, with the skill reference highlighted in the prompt

Example prompts

  • "Use the problem-framing skill on this prompt: our board wants 15% growth next year and nobody agrees on how."
  • "Use the market-sizing skill to size the market for mid-market payroll software in the region."
  • "Use the option-generation skill now that we have the market read for entering the segment."
  • "Use the board-memo skill to turn this roadmap into a two-page memo for Thursday's board meeting."

Tip

Name the skill in your prompt instead of describing the task. Phrases like "use the roadmap-design skill" point Claude at the exact method instead of leaving it to guess which one applies.

How to choose a skill

Match your immediate question to the skill that answers it. The table below picks one skill per question, but the pack ships 30 in total across 5 phases. For a wider set of standalone strategy skills beyond this engagement, see our 10 Claude Skills for Strategy Professionals.

Your question
Skill to use
What exactly are we trying to answer?
Problem Framing · Diagnose
What is the current state and who has to say yes?
Situation Assessment · Diagnose
How big is this market, really?
Market Sizing · Map
Where does the competition leave white space?
Competitor Mapping · Map
Which paths could we actually take?
Option Generation · Choose
Do the numbers on each option hold up?
Financial Modeling · Choose
How do we sequence the chosen strategy?
Roadmap Design · Execute
What could sink the plan, and how do we cover it?
Risk Assessment · Execute
How do we write this up for the board?
Board Memo · Communicate
How do we run the room to a decision?
Readout Facilitation · Communicate

The quality bar

Every skill is designed to hold output to the standard a senior reviewer would apply before a recommendation leaves the room.

One stated question, not five
MECE issue trees with no overlapping branches
Market sized both top-down and bottom-up
Every option scored against the same weighted criteria
Economics shown before conviction
Roadmap phased with named owners, not just labels
Risks paired with a concrete mitigation, not a shrug
Leading and lagging KPIs defined before launch
Recommendation stated on the first line of every memo
Confirmed figures marked apart from assumptions
No invented numbers, ever
Built for the board, not just the deck

Frequently asked questions

What is this Claude skills pack for running a strategy engagement?

It is 30 standalone Claude skills organized into the 5 phases of a full strategy engagement: Diagnose, Map, Choose, Execute, and Communicate, with 6 skills in each phase. Each skill is a single markdown file that teaches Claude a named, repeatable method for one job, and ships with example prompts. Across the pack that is 150 example prompts, and running the whole engagement end to end is roughly a 50-agent workflow, with each phase synthesized before it feeds the next.

How do I install these Claude skills?

Download the zip, then either create a Claude Project on claude.ai and upload the SKILL.md files as project knowledge, or drop the skill folders into ~/.claude/skills/ if you use Claude Code. Both routes are covered in the setup guide below.

Can I run all 30 skills in a single Claude Project?

Yes. Add the SKILL.md files to one project as project knowledge documents and reference each skill by name in your prompts. Claude reads the relevant skill automatically in every conversation inside that project, so the output of one skill can feed directly into the next. Most teams run the 30 skills as a ~50-agent workflow across the pack's 150 example prompts, synthesizing each phase before moving to the next.

Does this replace hiring a strategy team?

No. The skills replace the assembly work behind a full-scope engagement: framing the question, building the market read, comparing options, drafting the roadmap and the memo. The judgment, the client relationship, and the final call stay with your team. The skills exist so that work happens in hours instead of weeks.

How does this connect to Oria?

Claude and these skills handle the diagnosis, the analysis, and the memo. Oria handles the presentation layer. Paste the board memo, the roadmap, or the option comparison into Oria inside PowerPoint, and it converts the text into a fully editable slide in your corporate template in two to three minutes, instead of a manual formatting pass.