Can I use this with my existing GitHub issues?

Yes, it leverages the GitHub CLI to list milestones and label issues, allowing you to connect your strategic artifacts directly to your engineering implementation.

Does this skill require specific file structures?

It looks for and manages files within a `/strategy/` directory, including documents like VISION.md, STRATEGY.md, and OKRs.md to keep your project organized.

How does the skill detect when I'm planning?

The skill monitors for specific triggers such as discussions about build order, project scope, success metrics, or questions like 'what should we focus on next?'

Will this interrupt my normal coding flow?

No, it is designed to be helpful but not pushy. It triggers only on substantial planning discussions and offers structure as an optional tool rather than a requirement.

Strategic Planning

Name: Strategic Planning
Author: drewdresser

bydrewdresser

0•

协作工具

Detects planning-related discussions to guide users toward structured strategy artifacts, project roadmaps, and prioritized development workflows.

The Strategic Planning skill transforms Claude into a high-level project advisor that bridges the gap between abstract ideas and structured execution. It automatically monitors conversations for signals regarding project vision, MVP scoping, or feature prioritization, and suggests the creation of standardized documentation like VISION.md, OKRs, and User Stories. By integrating with the GitHub CLI, it allows users to connect high-level strategy directly to repository milestones and issues, ensuring that every line of code serves a documented goal and preventing scope creep through proactive alignment checks.

主要功能

01Alignment checking against project non-goals and success metrics

02Automatic detection of strategic planning and prioritization signals

03GitHub CLI integration for milestone tracking and issue management

04Structured workflows for defining MVPs and technical roadmaps

05Guided creation of strategy artifacts including Vision, OKRs, and Metrics

060 GitHub stars

使用场景

01Converting stakeholder discussions into actionable GitHub milestones and user stories

02Defining a project North Star and strategy before writing the first line of code

03Managing scope creep by validating new feature requests against existing non-goals

What are Skills?·How to Install

Install with 🐟 Skill.Fish

npx skillfish add drewdresser/ai-dev-settings strategic-planning

For use in Claude.ai and ChatGPT

Download Skill