HomeSkillsSkills for StrategyAndrew PershJuly 5, 202612 min read

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.

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

1

Phase 1 of 5 · 6 skills

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.

1.1

Problem Framing

problem-framing

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

1.2

Situation Assessment

situation-assessment

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

1.3

Stakeholder Mapping

stakeholder-mapping

What it does: Map who decides, who influences, and who blocks, then plan how to win each of them

1.4

Issue Tree Builder

issue-tree-builder

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

1.5

Hypothesis Generation

hypothesis-generation

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

1.6

Workplan Design

workplan-design

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

2

Phase 2 of 5 · 6 skills

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.

2.1

Data Gathering Plan

data-gathering-plan

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

2.2

Market Sizing

market-sizing

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

2.3

Competitor Mapping

competitor-mapping

What it does: Profile the competitive field, positioning, and moves to find where the white space is

2.4

Customer Segmentation

customer-segmentation

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

2.5

Interview Synthesis

interview-synthesis

What it does: Turn raw interview and call notes into ranked, evidence-backed findings and quotes

2.6

Value Chain Analysis

value-chain-analysis

What it does: Map the value chain and cost-to-serve to expose where margin and leverage really sit

3

Phase 3 of 5 · 6 skills

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.

3.1

Option Generation

option-generation

What it does: Generate a genuinely distinct set of strategic options, not three flavors of the same idea

3.2

Scenario Modeling

scenario-modeling

What it does: Build base, upside, and downside scenarios with named drivers and tipping points

3.3

Financial Modeling

financial-modeling

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

3.4

Prioritization Scoring

prioritization-scoring

What it does: Score options against weighted criteria to force a defensible, transparent ranking

3.5

Business Case Builder

business-case-builder

What it does: Assemble the recommended option into a full business case a board can actually approve

3.6

Recommendation Synthesis

recommendation-synthesis

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

4

Phase 4 of 5 · 6 skills

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.

4.1

Roadmap Design

roadmap-design

What it does: Sequence the chosen strategy into phased workstreams, milestones, and dependencies

4.2

Operating Model Design

operating-model-design

What it does: Design the org, roles, and decision rights needed to actually run the new strategy

4.3

Initiative Charter

initiative-charter

What it does: Charter each major initiative with scope, owner, success metrics, and resourcing

4.4

Risk Assessment

risk-assessment

What it does: Surface the risks that could sink the plan and pair each with a concrete mitigation

4.5

KPI Dashboard Design

kpi-dashboard-design

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

4.6

Change Management Plan

change-management-plan

What it does: Plan the people side of the change so the strategy lands instead of stalling

5

Phase 5 of 5 · 6 skills

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.

5.1

Executive Summary

executive-summary

What it does: Write the one-page answer-first summary a busy executive reads before anything else

5.2

Board Memo

board-memo

What it does: Draft the board-ready memo that frames the decision, options, and the ask

5.3

Presentation Narrative

presentation-narrative

What it does: Build the storyline and slide flow that carries an audience from problem to decision

5.4

Slide Drafting

slide-drafting

What it does: Turn each storyline point into a single-message slide with a real action title

5.5

Objection Handling

objection-handling

What it does: Pre-empt the hardest questions and rehearse crisp, evidence-backed answers

5.6

Readout Facilitation

readout-facilitation

What it does: Plan and run the decision meeting so the room leaves aligned on a commitment

Setup Guide

  1. Step 1

    Download the pack and open Settings

    Download all 30 skills (.zip)

    Download and unzip the pack, keeping each of the 30 skills in its own folder with its SKILL.md file. In Claude, open your profile menu and select Settings.

    Claude profile menu with Settings highlighted
    Open the screenshot to view it full size.
  2. Step 2

    Open Skills and start an upload

    In Settings, select Skills under Customize. Open Add and choose Upload a skill.

    Claude Skills settings with Add and Upload a skill highlighted
    Open the screenshot to view it full size.
  3. Step 3

    Upload one skill file

    Open one extracted skill folder and drag its SKILL.md file into the upload window, or use the file picker. Repeat for each skill or phase you want to add.

    A SKILL.md file being dragged into Claude's skill upload window
    Open the screenshot to view it full size.
  4. Step 4

    Confirm the skill was added

    Return to the Skills list and check that the skill appears. Select its name to open it.

    Claude Skills list with the uploaded CIM Drafting skill highlighted
    Open the screenshot to view it full size.
  5. Step 5

    Review and turn on the skill

    Review the skill's name, description, and instructions, then make sure the switch beside Share is on. A blue switch means the skill is turned on; sharing it is optional.

    CIM Drafting skill details with the enabled toggle highlighted
    Open the screenshot to view it full size.

Try a skill

Name the skill you want Claude to use and provide the relevant brief, evidence, and constraints. Review every output before it feeds the next phase.

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

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 and unzip the pack, open Settings in Claude, select Skills under Customize, and use Add, then Upload a skill. Upload the SKILL.md file from each skill folder you want to use, confirm it appears in the list, and make sure it is turned on. The current five-step flow is shown below.

Can I add and run all 30 skills in Claude?

Yes. Upload the SKILL.md files through Claude's Skills settings and reference the relevant skill by name in your prompts. 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 Academy?

The pack gives Claude reusable methods for a full strategy engagement. Oria Claude Academy teaches the broader AI workflows and operating habits that help professionals use tools like these consistently, review their output, and build repeatable ways of working across a team. Use the pack for the engagement itself and the Academy to deepen the surrounding workflow.