Ready to supercharge your AI agents?

Install any skill in seconds. Free to start, no credit card required.

Get Started Free →

Roadmap Planning · getcrew44 | DecimalAI

productivityby getcrew44

Roadmap Planning

getcrew44/roadmap-planning

Source getcrew44/crew44 ↗License MIT

Plan a strategic roadmap across prioritization, epic definition, stakeholder alignment, and sequencing.

SkillScore82Maintained

Automatic

Product Management pack

Last verified 8/23/2026

What it changes

Passed 18 of 22 test cases with the skill, and 10 of 22 without it.

Without skill45%

With skill82%

Checks it passed that the model alone missed

Define 'Now' as current quarter committed work.
Specify allocating approximately 60 minutes per epic hypothesis.
Include the 'because [assumption]' clause within all epic hypothesis statements.

and 8 more in the full report

8 fixed10 passed either way4 still failing0 broke

Pass-rate lift: +36 pp
Tokens: +142%
Agent turns: 0%
Response time: -31%

Model gemini-3.6-flashMeasured 8/23/2026v118 of 22 cases passed with skill

Tokens, turns and time describe resource use, not a dollar price.

Use this skill

Save it into your project's skills folder. Claude Code picks it up in its next session.

curl -fsSL --create-dirs -o .claude/skills/getcrew44-roadmap-planning/SKILL.md https://app.decimal.ai/s/getcrew44-roadmap-planning/SKILL.md

Want it pinned and updatable? pip install "decimalai>=0.15", then decimalai skills add getcrew44-roadmap-planning, and start Claude Code with claude --plugin-dir "$(git rev-parse --show-toplevel)/.agents"

1 · One-time — install the CLI (docs ↗)

pip install "decimalai>=0.15"

2 · Get the skill — writes .agents/skills/getcrew44-roadmap-planning/ and pins it in .decimal/skills.lock

decimalai skills add getcrew44-roadmap-planning

No CLI? Get the same file — curl · raw file

curl -fsSL --create-dirs -o .claude/skills/getcrew44-roadmap-planning/SKILL.md https://app.decimal.ai/s/getcrew44-roadmap-planning/SKILL.md

Raw file: /s/getcrew44-roadmap-planning/SKILL.md ↗ · machine-readable summary at /s/getcrew44-roadmap-planning.json ↗

Safety checks: 3 of 3 passed

Code scan CleanIntent PassedContent Clean

See it in action

One of 8 test cases the skill fixed. Same model, same prompt, with and without the skill.

1 of 8

Prompt

Our engineering team starts Sprint 24 tomorrow. I have 10 Jira user stories in our backlog. Can you help me break down these specific stories into sub-tasks and assign story point estimates (1, 2, 3, 5, 8) for this two-week sprint?

What was checked, without and with the skill
Checked	Without skill	With skill
Decline to run strategic roadmap planning for immediate sprint backlog point estimation.	Missed	Passed
Direct the user to perform tactical sprint planning or backlog refinement instead.	Missed	Passed

case-04 · gemini-3.6-flash · 8/23/2026 · answers are capped and redacted

What's inside

The instructions your model reads when the skill loads.

SKILL.md487 linessingle file

Purpose

Guide product managers through strategic roadmap planning by orchestrating prioritization, epic definition, stakeholder alignment, and release sequencing skills into a structured process. Use this to move from disconnected feature requests to a cohesive, outcome-driven roadmap that aligns stakeholders, sequences work logically, and communicates strategic intent—avoiding "feature factory" roadmaps that lack strategic narrative or customer-centric framing.

This is not a Gantt chart—it's a strategic communication tool that shows what you're building, why it matters, and how it ladders up to business outcomes.

Key Concepts

What is Strategic Roadmap Planning?

Roadmap planning is the process of:

Gathering inputs — Customer problems, business goals, technical constraints
Defining initiatives — Epics with clear hypotheses and success metrics
Prioritizing — Rank initiatives by impact, effort, strategic fit
Sequencing — Organize into releases/quarters with logical dependencies
Communicating — Present roadmap to stakeholders with strategic narrative

Types of Roadmaps

Now/Next/Later Roadmap:

Now: Current quarter (committed)
Next: Following quarter (high confidence)
Later: Future exploration (low confidence)
Best for: Agile teams, uncertainty, continuous discovery

Theme-Based Roadmap:

Organize by strategic themes (e.g., "Retention," "Enterprise Expansion," "Mobile Experience")
Best for: Communicating to execs, showing strategic intent

Timeline Roadmap (Quarters):

Q1: Epics A, B; Q2: Epics C, D; Q3: Epics E, F
Best for: Resource planning, stakeholder communication

Feature-Based Roadmap (Anti-Pattern):

Lists features without context (e.g., "Dark mode," "SSO," "Advanced reporting")
Why it fails: No strategic narrative, no customer problems framed

Why This Works

Outcome-driven: Ties initiatives to business/customer outcomes
Stakeholder alignment: Transparent process reduces political friction
Strategic clarity: Shows not just "what" but "why"

Track record

Benchmark

18 / 22

test cases passed, vs 10 / 22 without

Adoption

Users: 0
Times used: 0

Safety and source details

SkillSafety

✓ 3 of 3 passed

Code scan15 of 15 checks clean

0 critical · 0 warning · 0 info — scanner v4 — 8/3/2026

View 15 scanner checks

live_secretremote_code_executionreverse_shelldata_exfiltrationssrf_metadataagent_snoopinganti_refusaldestructive_commandsobfuscated_unicodeunicode_homoglyphopaque_blobsuspicious_urltool_overreachtrigger_abuseprompt_injection_phrasing

IntentSafe

LLM judge · does the skill do what it claims

ContentClean

LLM judge · policy & harmful-content review

Source

Imported

getcrew44 / crew44

daemon/internal/presets/defaultcrew/skills/product/roadmap-planning/SKILL.md

View on GitHub ↗

License MITImported 8/3/2026Version v1

Other skills for the same job

Published skills whose descriptions closely match this one, with their headline benchmark lift.

More skills from the same source and nearby in the registry, with their headline benchmark lift.