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strategic-roadmap

Use when the user asks "what should I work on in this repository?", "what is worth doing next?", requests a repository audit, technical debt priorities…

Skill by TheCheepeer

IndexedApache-2.0
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Works with Claude Code, Claude apps, Codex, Cursor, Gemini CLI, GitHub Copilot, VS Code, OpenCode, Goose, Windsurf. Read the repository before you give any tool access to your data.

npx agentmarket install skill/thecheepeer-strategic-roadmap

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About

Use when the user asks "what should I work on in this repository?", "what is worth doing next?", requests a repository audit, technical debt priorities, architecture assessment, or strategic discovery of code-grounded opportunities. Generates a roadmap artifact sequenced into Now/Next/Later, discarded items with rationale, and recommended next artifacts. Not for standard commercial product roadmaps.

Use cases: security

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What this skill can do and what it asks for, from its SKILL.md. Checked Oct 25, 2026.

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Network hosts it talks to 1

  • codeload.github.com · found in install command

Files it touches

  • ~/.claude/skills/strategic-roadmap

What's inside

Skill name
strategic-roadmap
Description
Use when the user asks "what should I work on in this repository?", "what is worth doing next?", requests a repository audit, technical debt priorities, architecture assessment, or strategic discovery of code-grounded opportunities. Generates a roadmap artifact sequenced into Now/Next/Later, discarded items with rationale, and recommended next artifacts. Not for standard commercial product roadmaps.
License
Apache-2.0
Instructions
55 lines in SKILL.md · view on GitHub

Files (3)

  • README.md
  • SKILL.md
  • roadmap-template.md · references/

SKILL.md (first lines)

# Strategic Repository Roadmap (Strategic Roadmap)

Plan the work that is genuinely worth doing in a repository. This is a senior, audit-based judgment phase: mine project documentation, past plans, active branches, and code architecture; analyze opportunities across improvement categories; expand upon user-provided ideas; surface non-obvious improvements; discard low-value work; and sequence the highest-leverage initiatives.

Treat this as meta-engineering: prefer structural improvements that enhance future development cycles, automated verification, autonomy boundaries, and codebase health over disconnected spot fixes.

## Sources and References

Before producing the roadmap, leverage corresponding skills and references:

- `improve` for evidence-based auditing and "not worth doing now" verdicts.
- `coding-standards` as the canonical source for vocabulary and architectural idioms (deep modules, state boundaries, boundary parsing).
- Project documentation: `GEMINI.md`, `AGENTS.md`, `README.md`, ADRs, and open issues.

## Workflow

### 1. Define Scope and Repository Goals

- Identify the specific repository and existing artifacts.
- Clarify what "better" means for this project: end-user value, delivery velocity, test verification robustness, complexity reduction, or operational reliability.
- Include user-suggested ideas as starting points, not the exhaustive list.
- If primary goals are ambiguous, ask a brief alignment question before ranking items.

### 2. Non-Mutating Reconnaissance

- Read context and existing plans before judging.
- Identify test and build commands, active branches, and hot areas of recent Git churn.
- **Do not modify source code.** Produce only the roadmap artifact.
- If credentials or secrets are spotted, cite only path and line; never transcribe secret values.

### 3. Opportunity Audit

- Audit core categories: correctness/bugs, security, performance, tests, technical debt, migrations, tooling, and documentation.
- Identify decisions repeatedly re-debated by the team; propose stable policies or ADRs to settle them.
- Apply objective architectural criteria: where comprehension requires jumping across dozens of files, where interfaces are nearly as complex as their implementations, and where boundaries leak internal details.
- Do not propose final interfaces at this stage: capture friction, recommended direction, and the next planning artifact.

### 4. Validation and Sequencing

- Open cited code to verify each opportunity; never trust unverified tool outputs blindly.
- Order by **leverage**: expected impact divided by probable effort, weighted by technical confidence.
- Establish autonomy tiers: routine delegation to executors, design review, or direct human sign-off.
- Formally record discarded or deferred ideas to prevent them from being redundantly rediscovered in future audits.

### 5. Draft the Roadmap

- Create `.agents/ROADMAP.md` (or project equivalent) using the template in [references/roadmap-template.md](references/roadmap-template.md).
- Prefer **Now / Next / Later** sequencing over arbitrary dates.
- Every item must indicate its next planning artifact: `roadmap-to-improve-plans`, `feature-planning-artifacts`, `research spike`, `user decision`, or `discard`.

## Completion Criteria

The strategic roadmap is complete when any developer or future agent can pick the next work item without re-scanning the entire repository: top opportunities are ranked with evidence, discarded ideas are documented with rationale, and the next planning step is explicit.

From TheCheepeer/omni-agents, Apache-2.0.

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Last commit (this folder)
Sep 28, 2026 (1 month ago)

From GitHub (fetched Oct 24, 2026).

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License
Apache-2.0
First seen
Oct 24, 2026
Last checked
Oct 24, 2026

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strategic-roadmap skill. Agent Mart. https://agentmart.dev/skills/thecheepeer-strategic-roadmap (last updated 2026-10-24)