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?

Run evals on this skill

Adds up to 20 points to the overall score

View guide

Securityby

Passed

No findings from the security scan

Quality

Content

78%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.

The content is a well-structured, opinionated planning skill: a clear 5-layer framework and 8-step workflow with concrete defaults and a cleanly separated reference file. Its main weakness is mild redundancy between the layer explanations and the failure-patterns section, which keeps conciseness just below the top anchor.

Suggestions

Consolidate the capacity-fantasy point so it appears once (Layer 4 or Failure patterns) with a cross-reference, trimming repeated prose to lift conciseness toward 5.

Inline a one-line RICE/MoSCoW worked example in Step 3 so prioritization is actionable without forcing a file hop, closing the minor actionability gap.

Add an explicit 'replan if team validation fails' loop in Step 6 (validate → adjust → re-validate) to give workflow_clarity a full feedback cycle.

Dimension	Reasoning	Score
Conciseness	The body is mostly efficient and opinionated ('A roadmap without strategy is just a queue'), assuming Claude's competence rather than re-explaining basics. It is not a 5 because some material repeats across the 5-layer framework and the 'Failure patterns' section (e.g., capacity fantasy appears in both), which could be tightened.	4 / 5
Actionability	Provides concrete, executable guidance: default capacity percentages (60-70% engineers, 50-60% designers), S/M/L/XL sizing, named prioritization frameworks, and explicit per-item fields (Name, Theme, Source, Owner, Status). Not a 5 because the actual prioritization math is delegated to the reference file, leaving a few minor gaps inline; as an instruction-only skill the absence of code is not penalized.	4 / 5
Workflow Clarity	An 8-step workflow is clearly sequenced with explicit validation checkpoints — 'If the strategy is missing or vague, stop', 'Validate with the team', and 'Before sharing externally, validate'. Not a 5 because, being a planning rather than a fragile/destructive operation, the feedback loops are lighter and lack the validate→fix→retry rigor of the top anchor; not a 3 because checkpoints are explicit, not merely implicit.	4 / 5
Progressive Disclosure	The body is a clear overview with a single well-signaled, one-level-deep reference — 'See references/prioritization-frameworks.md' inline and again in a 'Reference files' section — and the detailed framework breakdown is appropriately split into that verified file. Easy to navigate with no nested references, matching the top anchor.	5 / 5
	Total	17 / 20 Passed

Description

100%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.

The description is strong across all dimensions: it states concrete capabilities, provides a rich set of natural trigger phrases, and explicitly covers both what the skill does and when to use it. It carves out a distinct roadmap-planning niche with low conflict risk.

Dimension	Reasoning	Score
Specificity	Lists multiple concrete actions — 'Build a multi-quarter roadmap', 'sequencing dependent work', 'balancing build vs improve vs maintain', 'making the case for what NOT to do' — with comprehensive coverage of the planning domain. Not a 4 because the actions go beyond minor gaps into full coverage of build/improve/maintain and explicit rejection.	5 / 5
Completeness	Explicitly answers both 'what' ('Build a multi-quarter roadmap from a backlog...') and 'when' ('Use this skill when planning the next quarter...'; 'Triggers on...') with concrete trigger phrases. Clearly matches the 5 anchor; not a 4 because the 'when' is explicit and specific rather than weakly implied.	5 / 5
Trigger Term Quality	Comprehensive natural trigger phrases a user would actually say: 'roadmap', 'quarterly planning', 'what should we build next', 'OKR planning', 'capacity planning', 'plan the year', plus the stakeholder-conflict scenario. Includes synonyms and phrasings rather than jargon, so it sits at the top anchor rather than 4.	5 / 5
Distinctiveness Conflict Risk	Occupies a clear niche (roadmap/quarterly planning) with distinct triggers unlikely to fire for adjacent skills like spec-writing or ux-research. Minor conceptual overlap with prioritization is bounded by roadmap-specific phrasing, keeping it at 5 rather than 4.	5 / 5
	Total	20 / 20 Passed

Validation

93%

Warnings & errors only

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

Criteria	Description	Result
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
Commit: 0479242

Reviewed: 14 days ago

Table of Contents

Discovery Implementation Validation

Is this your skill?

If you maintain this skill, you can claim it as your own. Once claimed, you can manage eval scenarios, bundle related skills, attach documentation or rules, and ensure cross-agent compatibility.