Develop a strategy using the Playing to Win cascade — Winning Aspiration, Where to Play, How to Win, Capabilities, and Management Systems. Use when you need to make strategic choices about markets, positioning, and competitive advantage.
80
76%
Does it follow best practices?
Impact
Pending
No eval scenarios have been run
Passed
No known issues
Optimize this skill with Tessl
npx tessl skill review --optimize ./product-skills/skills/playing-to-win/SKILL.mdQuality
Discovery
75%Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.
The description is well-structured with a clear 'what' and 'when' clause, and the named framework provides strong distinctiveness. However, it could be more specific about concrete actions/outputs and include more natural trigger terms users might use when seeking strategic planning help.
Suggestions
Add more specific concrete actions like 'analyze competitive positioning, identify target markets, define capability requirements, and produce a strategy cascade document'
Expand trigger terms to include common variations like 'business strategy,' 'strategic planning,' 'Roger Martin,' 'strategy framework,' or 'competitive strategy'
| Dimension | Reasoning | Score |
|---|---|---|
Specificity | Names the domain (strategy) and lists the five elements of the Playing to Win cascade, but doesn't describe concrete actions beyond 'develop a strategy.' It doesn't specify outputs like 'generate a strategy document' or 'map competitive positioning.' | 2 / 3 |
Completeness | Clearly answers both 'what' (develop a strategy using the Playing to Win cascade with its five components) and 'when' (explicit 'Use when you need to make strategic choices about markets, positioning, and competitive advantage'). | 3 / 3 |
Trigger Term Quality | Includes some relevant keywords like 'strategic choices,' 'markets,' 'positioning,' 'competitive advantage,' and 'Playing to Win,' but misses common variations users might say such as 'business strategy,' 'strategy framework,' 'where to play how to win,' 'Roger Martin,' or 'strategic planning.' | 2 / 3 |
Distinctiveness Conflict Risk | The Playing to Win cascade is a specific, named framework with distinct terminology (Winning Aspiration, Where to Play, How to Win, Capabilities, Management Systems), making it clearly distinguishable from generic strategy skills or other frameworks. | 3 / 3 |
Total | 10 / 12 Passed |
Implementation
77%Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.
This is a well-structured strategic analysis skill with excellent actionability — the output template is comprehensive and immediately usable, and the workflow is clearly sequenced with validation checkpoints. The main weaknesses are moderate verbosity in the cascade descriptions (explaining concepts Claude likely knows about strategy frameworks) and a somewhat monolithic structure where the lengthy output template could benefit from being in a separate reference file. Overall, it's a strong skill that would effectively guide Claude through strategic analysis.
Suggestions
Trim the cascade descriptions — Claude understands strategic concepts like cost leadership vs. differentiation and value chain positioning. Focus on the specific choices and constraints rather than defining terms.
Consider moving the full output template to a separate reference file (e.g., references/template.md) and keeping only a brief summary of the expected output structure in the main SKILL.md.
| Dimension | Reasoning | Score |
|---|---|---|
Conciseness | The content is mostly efficient but includes some unnecessary elaboration. Phrases like 'not a to-do list dressed up as one' and explanations of what a winning aspiration is ('A winning aspiration sets the purpose and frames every subsequent choice') add flavor but not actionable value. The cascade descriptions could be tighter since Claude understands strategic frameworks. However, it avoids truly egregious padding. | 2 / 3 |
Actionability | The skill provides a complete, copy-paste-ready output template with specific markdown structure, tables, and clear fields to fill. The workflow steps are concrete and sequenced, the coherence check includes specific diagnostic questions, and the 'Adapting the Analysis' section gives actionable guidance for different contexts. The must-be-true conditions table and next steps are particularly actionable. | 3 / 3 |
Workflow Clarity | The five-step workflow is clearly sequenced with explicit ordering ('each choice constrains the next'). Step 3 provides a coherence validation checkpoint with specific diagnostic questions. Step 5 reverse-engineers must-be-true conditions as a verification mechanism. The cascade structure itself is a natural feedback loop — if coherence fails, you revisit earlier choices. | 3 / 3 |
Progressive Disclosure | The skill references [framework.md](references/framework.md) for detailed definitions and diagnostic questions, which is good progressive disclosure. However, no bundle files were provided, so we can't verify the reference exists. The output template is quite long and could potentially be split into a separate reference file. The tips section references other skills (7-powers, amazon-working-backwards, pre-mortem) which is good cross-referencing but the main content is somewhat monolithic. | 2 / 3 |
Total | 10 / 12 Passed |
Validation
90%Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.
Validation — 10 / 11 Passed
Validation for skill structure
| Criteria | Description | Result |
|---|---|---|
frontmatter_unknown_keys | Unknown frontmatter key(s) found; consider removing or moving to metadata | Warning |
Total | 10 / 11 Passed | |
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