Is playing-to-win safe to install?

SaferSkills independently audited playing-to-win (Agent Skill) and scored it 100/100 (green). The audit ran 55 deterministic rules across Security, Supply Chain, Maintenance, Transparency, and Community; it found 0 high-severity and 0 lower-severity findings. The full rule-by-rule trace and per-finding evidence are below. Free, methodology-open.

CategoryWeightCategory scoreContribution

Securityprompt, exec, net, exfil, eval

35%

100

35.0 pts

Supply chainhash, typosquat, maintainer, lockfile

20%

100

20.0 pts

Maintenancestaleness, pinning, CI

15%

100

15.0 pts

TransparencySKILL.md, perms, README

15%

100

15.0 pts

Communityinstalls, verify, response

15%

100

15.0 pts

Findings & checks · 0 flagged

Securityscore 100 · 0 findings

✓—All security checks passedNo findings in this category for the latest scan.pass

Supply chainscore 100 · 0 findings

✓—All supply chain checks passedNo findings in this category for the latest scan.pass

Maintenancescore 100 · 0 findings

✓—All maintenance checks passedNo findings in this category for the latest scan.pass

Transparencyscore 100 · 0 findings

✓—All transparency checks passedNo findings in this category for the latest scan.pass

Communityscore 100 · 0 findings

✓—All community checks passedNo findings in this category for the latest scan.pass

The primary manifest — the file an agent reads to learn what this artifact does.

skills/reasoning-strategy/playing-to-win/SKILL.md · 1 file

skills/reasoning-strategy/playing-to-win/SKILL.md20.5 KB · Markdown

name: playing-to-win

# description: routing-facing summary of when this skill activates and what it covers.

description: "Use when turning a vague business strategy, product strategy, market-entry decision, or initiative plan into an integrated Playing to Win strategy cascade: winning aspiration, where to play, how to win, must-have capabilities, and management systems. Covers Lafley/Martin choice-making, fit across the five choices, trade-off pressure, reverse tests, capability-system alignment, and the difference between strategy and planning. Do NOT use for competitive-industry structure analysis (use a five-forces skill when available), generic backlog scoring (use prioritization), or broad process-gate design (use methodology)."

# license: SPDX-compatible license identifier for the skill content.

license: MIT

# compatibility: runtime and portability notes for this skill.

compatibility:

notes: "Markdown, strategy memos, product strategy, executive decision-making"

allowed-tools: Read Grep

# metadata: Skill Metadata Protocol fields encoded under Agent Skills-compatible frontmatter.

metadata:

# schema_version: protocol contract version this skill conforms to.

# Integer 8. Prior contract retrievable via `git show schema-v7:schemas/skill.schema.json`.

# version: skill content version (semver). Bumped when the instructional content changes.

# === v8 Classification (subject + public; polyhierarchy via subjects[]) — see ADR-0020 ===

# subject: primary browse shelf — what the skill teaches. One of twelve closed values:

# backend-engineering / frontend-engineering / software-architecture / data-engineering / agent-ops / ai-engineering /

# quality-assurance / design / reasoning-strategy / software-engineering-method / knowledge-organization / product-domain.

subject: reasoning-strategy

# public: publishability / private-data gate. true = safe for public release; false = private/internal.

public: true

# scope: required free-text statement of what this skill teaches and what it does not.

scope: "Use when turning a vague business strategy, product strategy, market-entry decision, or initiative plan into an integrated Playing to Win strategy cascade: winning aspiration, where to play, how to win, must-have capabilities, and management systems. Covers Lafley/Martin choice-making, fit across the five choices, trade-off pressure, reverse tests, capability-system alignment, and the difference between strategy and planning. Do NOT use for competitive-industry structure analysis (use a five-forces skill when available), generic backlog scoring (use prioritization), or broad process-gate design (use methodology)."

# public: publishability / private-data gate. true = safe for public release; false = private/internal.

# Project anchoring lives in project[] and requires grounding when present.

# taxonomy_domain: optional hierarchical sub-path within `subject`. Slash-delimited

# lowercase kebab-case segments. rename of the original v8 `domain`. Remove when the flat

# `subject` is sufficient.

taxonomy_domain: foundations/strategy

# owner: team handle, GitHub username, or tool name responsible for keeping this skill current.

# freshness: ISO date the skill body was last reviewed or updated.

# drift_check: truth-source verification record. Object with required `last_verified`

# (ISO date) and optional `truth_source_hashes`. Record hashes with:

# `node scripts/skill-graph-drift.js --record --apply <skill-dir>`.

# === Evaluation Status: three orthogonal axes ===

# eval_artifacts: disk-truth — does an eval file exist on disk?

# none (no intent) / planned (intent declared, no file yet) / present (file exists).

# eval_state: runtime-truth — has the eval been run and passed?

# unverified (no run yet, or no file) / passing (one-shot green) / monitored (cadenced green).

# `monitored` is strictly stronger than `passing` — a forward state for continuous runs.

# routing_eval: routing-coverage — is the skill's activation verified by the harness?

# absent (not verified) / present (gated by lint check 12; harness must exit 0).

# comprehension_state: marker that this skill has populated v6+ Understanding fields

# (mental_model, purpose, boundary, analogy, misconception). Value: `present` or absent.

# stability: lifecycle marker. One of:

# experimental (active development) / stable (production-ready) /

# frozen (no further changes expected) / deprecated.

# When `deprecated`, schema's allOf REQUIRES `superseded_by: <real-skill-name>`.

stability: stable

# keywords: semantic phrases for fuzzy router activation. v8 cap: max 10.

# Keep terms a user would actually type when starting a task in this skill's domain.

keywords: ["playing to win","strategy cascade","strategic choice cascade","winning aspiration","where to play","how to win","strategy choices","capability system","management systems","lafley martin"]

# examples: 2-5 realistic user prompts the skill SHOULD activate for.

# Written in the user's voice. Improves retrieval recall beyond keywords alone.

examples: ["turn this vague growth plan into a Playing to Win cascade","we need a product strategy for a narrow segment; help choose where to play and how to win","our strategy doc has goals and initiatives but no trade-offs; apply Lafley/Martin","pressure-test whether these capabilities actually support our how-to-win choice","rewrite this market-entry plan as winning aspiration, where to play, how to win, capabilities, and systems"]

# anti_examples: near-miss prompts that should route ELSEWHERE.

# Pair with relations.suppresses to indicate the confusable territory's owner.

anti_examples: ["analyze whether this industry has attractive supplier power and threat of substitutes","score these ten backlog items by impact and effort","design a quality gate process for this multi-step implementation","write OKRs for this strategy after it has already been chosen"]

# relations: typed graph edges to sibling skills. Six edge types:

# related (adjacency for browse / co-routing expansion) /

# suppresses (exclude listed skills from co-routing when THIS skill wins;

# write reason as "I own this exclusively over X", not "use X instead") /

# verify_with (cross-check; co-loaded as one-hop expansion) /

# depends_on (composition; transitive — A→B→C loads all three) /

# broader / narrower (SKOS-style generalization; broader drives co-load, narrower does not).

# grounding: required when non-empty `project[]`. Declares the truth sources

# the skill anchors to and the failure modes those sources prevent. Omit when the

# skill is universal-knowledge. `subject_matter` replaces v8 `domain_object`.

grounding: "{\"subject_matter\":\"Playing to Win strategy cascade by A.G. Lafley and Roger L. Martin\",\"grounding_mode\":\"universal\",\"truth_sources\":[\"https://hbr.org/books/playing-to-win\",\"https://hbr.org/webinar/2013/04/a-playbook-for-winning\",\"https://www-2.rotman.utoronto.ca/insightshub/strategy-value-creation/playing-to-win-how-strategy-re\",\"skills/reasoning-strategy/playing-to-win/references/playing-to-win-sources.md\",\"skills/reasoning-strategy/playing-to-win/references/upstream-displacement-2026-05-26.md\"],\"failure_modes\":[\"goal_list_without_choice\",\"where_to_play_too_broad\",\"how_to_win_not_differentiated\",\"capabilities_not_tied_to_advantage\",\"management_systems_missing\",\"cascade_choices_do_not_reinforce\",\"strategy_confused_with_planning\"],\"evidence_priority\":\"general_knowledge_first\"}"

# portability: external-runtime export claims. Object with:

# readiness — declared (claim only) / scripted (export tooling exists) /

# verified (proven with a receipt artifact).

# targets — array; currently only `skill-md` is in the enum.

# lifecycle: maintenance policy for the drift sentinel.

# stale_after_days — skill flagged STALE when N days past `drift_check.last_verified`.

# review_cadence — process commitment (quarterly / monthly / annual), not a calendar fact.

# === Understanding fields (when comprehension_state: present) ===

# mental_model: the primitives of the concept and how they relate. One paragraph.

mental_model: "Playing to Win treats strategy as five mutually reinforcing choices, not as a plan, goal list, or analysis deck. The primitives are a winning aspiration, a chosen playing field, a differentiated way to win there, the capabilities required to deliver that advantage, and the management systems that build and sustain those capabilities. The cascade works only when the answers fit together and force trade-offs."

# purpose: the problem this concept solves and why the field exists. One paragraph.

purpose: "This skill prevents agents from producing strategy-shaped prose that lacks choices. It replaces broad aspirations, market summaries, and initiative lists with an explicit cascade that says what the organization will do, what it will not do, why it can win in the chosen arena, and what must be true operationally for the choice to work."

# boundary: what this concept is NOT. Distinguishes from adjacent skills by naming the

# MECHANISM that differs, not just the label. Universal terms only — no repo-specific nouns.

concept_boundary: "Playing to Win is for strategy formulation and choice integration. It is not Porter's Five Forces industry-structure diagnosis, Seven Powers moat taxonomy, OKR execution tracking, generic prioritization, scenario planning, or full financial valuation. Those tools may feed or follow the cascade, but they do not replace the five integrated choices."

# analogy: one-sentence metaphor preserving the core mechanism.

analogy: "A strategy cascade is like designing a bridge from both banks at once: the aspiration and market choice define one side, the advantage and capability system define the other, and the bridge fails if the pieces do not meet in the middle."

# misconception: the wrong mental model people bring; corrected explicitly.

misconception: "The common mistake is filling the five boxes independently. The cascade is not a worksheet; changing one answer should force a re-check of the others, because an aspiration with no winnable arena is hope and a how-to-win with no supporting capabilities is fantasy."

# === Health Block (written by the audit loop, not hand-authored) ===

# See SKILL_AUDIT_LOOP.md § The Health Block. UNVERIFIED is the honest default.

# structural_verdict: form/export shape (gates 1-2, 7 — external mandates only).

# PASS / PASS_WITH_FIXES / FAIL / UNVERIFIED.

# truth_verdict: truth sources vs declared hashes (gates 3-6).

# PASS / DRIFT / BROKEN / UNVERIFIED.

# comprehension_verdict: gate 8 — cheap recitation smoke test. Never alone certifies.

# PASS / SHALLOW / REDUNDANT / UNVERIFIED / PROVISIONAL / SKIPPED_BASELINE_HIGH / NA.

# application_verdict: gate 9 — the primary quality signal. APPLICABLE is the only verdict

# that certifies the skill is USEFUL (grader-confirmed). PROVISIONAL = one model self-assessed.

# APPLICABLE / REDUNDANT / HARMFUL / MIXED / FALSE_POSITIVE / PROVISIONAL / UNVERIFIED.

relations:

related: ["prioritization","constraint-awareness","framework-fit-analysis","methodology","bcg-matrix"]

verify_with: ["methodology","epistemic-grounding","seven-powers"]

Playing to Win

Concept of the skill

Playing to Win treats strategy as five mutually reinforcing choices, not as a plan, goal list, or analysis deck.

Concept Card

What it is: Playing to Win is A.G. Lafley and Roger L. Martin's strategy-cascade method. It frames strategy as an integrated set of five choices: winning aspiration, where to play, how to win, must-have capabilities, and management systems.

Mental model: Strategy is not a document that collects goals and initiatives. It is a coherent choice system. Each answer narrows and constrains the next answer, then the later answers pressure-test the earlier ones.

Why it exists: Agents often produce generic strategy prose: "grow revenue," "serve customers," "differentiate," "execute well." The cascade forces the missing choices into the open: which customers, markets, channels, offers, advantage, activities, capabilities, measures, and routines.

What it is not: It is not an industry attractiveness analysis, a moat taxonomy, an OKR tree, a roadmap, a backlog-prioritization table, or a financial model. Those can support the cascade, but the cascade owns the integrated strategy choice.

Adjacent concepts: Strategic choice cascade, strategy choice, where-to-play/how-to-win, activity systems, capability systems, reverse testing, competitive advantage, trade-offs.

One-line analogy: Playing to Win is a set of interlocking gears: if one gear turns, the others must still mesh.

Common misconception: The five questions are not five independent brainstorm prompts. They must fit together and reinforce each other.

Coverage

This skill teaches agents to:

Convert strategy prose into the five cascade choices.
Separate strategy from planning, goals, initiatives, and analysis.
Make the where to play choice concrete across customer, geography, channel, product/service, value-chain stage, and occasion.
Make the how to win choice a real advantage, not a slogan.
Identify capabilities that are necessary because of the how-to-win choice.
Define management systems that build, measure, and sustain the capabilities.
Pressure-test fit across all five choices.
Surface trade-offs, no-go choices, and assumptions that must be true.

Philosophy of the skill

Playing to Win is useful because it makes strategy expensive in the right place: choice. A vague strategy feels easy because it refuses trade-offs. A real strategy creates tension. It chooses one arena over another, one advantage logic over another, one capability system over another, and one management rhythm over another.

The cascade is not a guarantee that the strategy is correct. It is a forcing function that makes the strategy inspectable. Once the choices are explicit, an agent can ask whether they fit, whether they are feasible, whether competitors can copy them, and what evidence would change the decision.

The Five Choices

Choice	Question	Good answer	Weak answer
Winning aspiration	What does winning mean for this organization or initiative?	Specific enough to guide choices and define success	"Be the best", "grow", "delight users"
Where to play	In which arenas will we compete?	Clear customer, segment, geography, channel, category, use case, or value-chain scope	"Everyone", "SMBs", "global market"
How to win	What advantage lets us win in that arena?	Distinct value equation, cost position, experience, access, speed, trust, data, or system advantage	"Better product", "great UX", "AI-powered"
Capabilities	What must we be excellent at to deliver that advantage?	Few must-have activities tied directly to how-to-win	Generic functions every company needs
Management systems	What routines, metrics, structures, and incentives sustain the capabilities?	Concrete review cadence, metrics, decision rights, resource allocation, learning loops	"Execute", "track KPIs", "communicate"

Workflow

1. Extract the current implied strategy

Read the existing plan and identify what it already implies.

Current aspiration:
Current where-to-play:
Current how-to-win:
Current capabilities:
Current management systems:
Unstated assumptions:
No-go choices:

If the source material only contains initiatives, infer the missing choices and label them as inferred. Do not present inferred choices as confirmed.

2. Make where-to-play concrete

Specify the arena with at least three dimensions when possible.

Dimension	Examples
Customer or user	enterprise admins, solo operators, first-time buyers, expert teams
Need or occasion	urgent repair, recurring workflow, high-risk decision, low-cost habit
Product or service category	onboarding tool, compliance service, analytics dashboard
Geography or regulation	US-only, EU-regulated, local-market dependent
Channel	self-serve, partner-led, marketplace, enterprise sales
Value-chain stage	discovery, purchase, fulfillment, operations, retention

The test: a competitor should be able to tell what you are choosing not to pursue.

3. Make how-to-win falsifiable

Describe why the chosen customers will prefer this offer against the relevant alternative.

Strong how-to-win statements name:

the target customer's job or pain,
the alternative they would otherwise use,
the specific value equation you improve,
the hard-to-copy system that makes the improvement durable enough,
the evidence that would show the advantage is working.

Weak how-to-win statements use adjectives without mechanism: better, easier, smarter, delightful, AI-powered, premium, trusted.

4. Tie capabilities to the advantage

Capabilities are not departments. They are things the organization must do unusually well because the how-to-win demands them.

Use this check:

If our how-to-win is true, we must be excellent at:
1.
2.
3.

If we are not excellent at those, the strategy fails because:

Keep the list short. A long list means the advantage is vague or the strategy is actually multiple strategies.

5. Define management systems

Management systems make the strategy persistent. They decide what gets measured, funded, reviewed, escalated, rewarded, and learned.

At minimum, define:

decision cadence,
owner for each capability,
leading indicators,
lagging indicators,
review ritual,
resource-allocation rule,
kill or pivot trigger.

If the cascade has no management systems, it is a workshop artifact, not an operating strategy.

Fit Checks

Run these checks before presenting the strategy as coherent.

Check	Failure signal	Repair
Aspiration/arena fit	The aspiration cannot be achieved in the chosen arena	Narrow or change aspiration, or choose a different arena
Arena/advantage fit	The how-to-win does not matter to the chosen customer	Rebuild the value proposition around that customer's real trade-off
Advantage/capability fit	Required capabilities are generic or missing	Name the few capabilities that make the advantage possible
Capability/system fit	No routines or metrics build the capabilities	Add operating mechanisms, owners, and review cadence
Trade-off clarity	Nothing is explicitly excluded	State no-go segments, channels, products, or behaviors
Reverse test	Competitors would happily choose the opposite	If not, the choice is probably a platitude

Output Template

Use this compact shape for strategy work.

Playing to Win cascade

Winning aspiration:

Where to play:
- Customer/segment:
- Need/occasion:
- Product/category:
- Geography/channel/value-chain scope:
- Explicit no-go:

How to win:
- Advantage:
- Relevant alternative:
- Why the target chooses us:
- Evidence that this is working:

Must-have capabilities:
1.
2.
3.

Management systems:
- Metrics:
- Cadence:
- Decision rights:
- Resource allocation:
- Kill/pivot trigger:

Fit risks:
- Choice mismatch:
- Assumption to test:
- Capability gap:

Boundaries

Use Playing to Win when the task is to define or repair the strategy choice system.

Use another tool when the task is narrower:

Need	Better owner
Industry structure, bargaining power, substitutes, entrants	Porter's Five Forces skill when available
Durable moat source taxonomy	Seven Powers skill when available
Creating execution objectives after strategy is chosen	OKRs skill when available
Ranking backlog items by effort, impact, confidence, or urgency	`prioritization`
Choosing which framework to apply	`framework-fit-analysis`
Designing quality gates or process methodology	`methodology`

Verification

Before finishing, verify:

[ ] The answer contains all five choices.
[ ] Where to play is narrow enough to exclude real alternatives.
[ ] How to win names a mechanism of advantage, not just an adjective.
[ ] Capabilities follow from the how-to-win choice.
[ ] Management systems include owners, metrics, cadence, and decision rights.
[ ] The choices reinforce each other.
[ ] At least one no-go trade-off is explicit.
[ ] Unverified assumptions are labeled as assumptions.
[ ] The response does not present a plan, roadmap, OKR tree, or market analysis as a strategy cascade.

References

references/playing-to-win-sources.md
references/upstream-displacement-2026-05-26.md

Do NOT Use When

Use another skill when the task falls outside the declared scope, matches an anti_examples prompt, or is owned by a more specific related skill.

playing-to-win— agent skill

Is playing-to-win safe to install?

Playing to Win

Concept of the skill

Concept Card

Coverage

Philosophy of the skill

The Five Choices

Workflow

1. Extract the current implied strategy

2. Make where-to-play concrete

3. Make how-to-win falsifiable

4. Tie capabilities to the advantage

5. Define management systems

Fit Checks

Output Template

Boundaries

Verification

References

Do NOT Use When

Audit the pieces. Scan the whole. Decide.