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roadmap-planning

Build a multi-quarter roadmap from a backlog of ideas, requests, and ongoing initiatives. Use this skill when planning the next quarter, sequencing dependent work, balancing build vs improve vs maintain, or making the case for what NOT to do. Triggers on roadmap, quarterly planning, what should we build next, sequencing, prioritization, OKR planning, capacity planning, what's on the roadmap, plan the year, what to ship next quarter. Also triggers when stakeholders are pulling in different directions and the team needs a defensible plan.

Quality

89%

Does it follow best practices?

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SecuritybySnyk

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SKILL.md
Quality
Evals
Security

Quality

Content

85%Weight 40%Scale 1-5

Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.

A high-quality instruction-only skill body: a clear five-layer framework, an 8-step workflow with explicit validation gates, concrete defaults and thresholds, and proper offloading of framework detail to a real, one-level-deep reference. The main improvement opportunities are de-duplicating the strategy-missing guidance and adding a brief worked example to make the output format fully concrete.

Suggestions

State the 'strategy must exist first' requirement once (Step 1 or Required inputs) and reference it elsewhere instead of repeating it three times.

Add a short worked example (one sample initiative brief or one filled-in 'Not now' entry with reason and re-entry trigger) to anchor the output format.

Trim rhetorical framing lines (e.g., the layer intro 'A roadmap is only as good as its weakest one') where the surrounding checklists already carry the point.

DimensionReasoningScore

Conciseness

Dense, opinionated guidance ("Engineers: 60-70% of time on roadmap initiatives", "If the math says the plan needs 100% of the team, the plan is wrong. Cut.") with no re-explanation of concepts Claude already knows. Not 5: the "strategy missing" point is repeated in Required inputs, the framework intro, and Step 1, and a few rhetorical asides could be trimmed.

4 / 5

Actionability

Concrete, executable instruction-guidance throughout: exact backlog-catalog fields (Name/Theme/Source/Size/Owner/Status), default capacity percentages by role, cadence rules ("month-by-month for one quarter, quarter-by-quarter beyond"), and a fixed output-section checklist. Not 5: no worked example (e.g., a sample initiative brief or a filled-in "Not now" entry) to anchor the most common case.

4 / 5

Workflow Clarity

Eight clearly sequenced steps with two explicit go/no-go gates ("If the strategy is missing or vague, stop"; "If the team says the plan is impossible, the plan is impossible. Adjust."), embedded warning flags (no-theme items, multiple unmet dependencies), and a failure-patterns section for error recovery. Checkpoints are explicit rather than implicit, matching the 5 anchor.

5 / 5

Progressive Disclosure

The body is a well-organized overview with one clearly signaled, one-level-deep reference: references/prioritization-frameworks.md exists, is linked twice with a description, and properly absorbs the deep framework detail (RICE math, MoSCoW buckets) that would otherwise bloat the main file. Matches the 5 anchor (clear overview, well-signaled references, appropriate split).

5 / 5

Total

18

/

20

Passed

Description

91%Weight 40%Scale 1-5

Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.

A strong description: concrete third-person capabilities, an explicit 'Use this skill when' clause with comprehensive natural trigger phrasing, and a distinct roadmap-planning niche. The only weakness is that it names actions but not the artifacts the skill produces, which slightly limits specificity and distinctiveness.

Suggestions

Mention the concrete outputs (the roadmap document, capacity model, and 'Not now' trade-off list) in the description to close the specificity gap.

Narrow the broadest trigger terms (e.g., "prioritization" alone) toward roadmap-specific phrasings to reduce overlap risk with generic prioritization or OKR skills.

DimensionReasoningScore

Specificity

Lists several concrete, third-person actions: "Build a multi-quarter roadmap from a backlog", "sequencing dependent work", "balancing build vs improve vs maintain", and "making the case for what NOT to do". Not 5 because it omits the concrete outputs the skill produces (the roadmap document, capacity model, "Not now" list), a minor coverage gap.

4 / 5

Completeness

Explicitly answers both: what ("Build a multi-quarter roadmap from a backlog of ideas, requests, and ongoing initiatives") and when ("Use this skill when planning the next quarter, sequencing dependent work...") with concrete trigger phrases. This matches the 5 anchor exactly; a 4 would require the 'when' clause to be less explicit.

5 / 5

Trigger Term Quality

"Triggers on roadmap, quarterly planning, what should we build next, sequencing, prioritization, OKR planning, capacity planning, what's on the roadmap, plan the year, what to ship next quarter" plus a situational trigger about stakeholders pulling in different directions — comprehensive natural terms including verbatim questions a user would actually type. Neighboring anchors (4: "a few natural terms missing") fit worse.

5 / 5

Distinctiveness Conflict Risk

Roadmap planning is a clear niche with distinct triggers, mostly distinguishable from adjacent PM skills. Not 5 because broad trigger terms like "prioritization" and "sequencing" carry minor overlap risk with generic prioritization/OKR skills; not 3 because the roadmap framing is far more specific than "somewhat specific".

4 / 5

Total

18

/

20

Passed

Validation

93%

Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.

Validation — 15 / 16 Passed

Validation for skill structure

CriteriaDescriptionResult

frontmatter_unknown_keys

Unknown frontmatter key(s) found; consider removing or moving to metadata

Warning

Total

15

/

16

Passed

Repository

rampstackco/claude-skills

Path

skills/roadmap-planning/SKILL.md

Reviewed

Table of Contents

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