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gsd-new-milestone

Initialize milestone kickoffs by updating PROJECT.md and generating numbered phase roadmaps.

Updated May 15, 2026
Search Tags:#project management#requirements gathering#roadmap generation#project documentation#milestone planning#brownfield projects#gsd workflow
One-click install
npx skills add https://github.com/Pear-Commerce/pear-ai-skills --skill gsd-new-milestone-pear-commerce
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: gsd-new-milestone
Source: https://github.com/Pear-Commerce/pear-ai-skills/tree/main/skills/gsd-new-milestone
Command: npx skills add https://github.com/Pear-Commerce/pear-ai-skills --skill gsd-new-milestone-pear-commerce

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This skill eliminates the friction of manually kicking off new project milestones for existing brownfield projects, ensuring all historical context from PROJECT.md is preserved and aligned with new goals, requirements, and roadmap plans.

Core Features & Use Cases

  • Automated Milestone Initialization: Updates the core PROJECT.md file with new milestone goals while retaining all existing project history and context.
  • Structured Requirements Gathering: Runs a guided questioning workflow to capture scope, constraints, and stakeholder needs for the new milestone.
  • Continuous Roadmap Generation: Creates a numbered phase roadmap that continues from prior milestone numbering, with optional domain research for brand new features. Use case: A product team that just launched v1.0 of their e-commerce platform can use this skill to kick off the v1.1 milestone, capture new feature requirements, and generate a phased roadmap that builds on the existing project context.

Quick Start

Invoke the gsd-new-milestone skill with your desired milestone name to automatically update project documentation and generate a structured requirements and roadmap plan for the upcoming work cycle.

Frequently Asked Questions about gsd-new-milestone

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I kick off a new milestone for an existing brownfield project without losing historical context?▼

To kick off a new milestone for an existing brownfield project, use an automated workflow that updates your core PROJECT.md file with new goals while preserving all prior project history and context. This ensures continuous alignment without manual documentation overhead.

What is the best way to gather requirements for a new project milestone?▼

The best way to gather requirements for a new project milestone is through a guided questioning workflow that captures scope, constraints, and stakeholder needs. This structured approach enforces planning validation gates to ensure complete alignment before roadmap generation.

Can I generate a phased roadmap that continues numbering from a previous milestone?▼

Yes, you can generate a continuous numbered phase roadmap that continues from prior milestone numbering. This allows iterative product and engineering teams to build phased development plans that logically extend existing project documentation.

Does milestone planning work for iterative development cycles on existing products?▼

Milestone planning works effectively for iterative development cycles on existing products. It applies to product and engineering teams running milestone-based development, capturing scoped requirements and updating core documentation to align with ongoing phased roadmaps.

How do I update project documentation for a new milestone without overwriting previous history?▼

You can update project documentation for a new milestone without overwriting previous history by using a structured initialization process. This automatically retains existing project context in your PROJECT.md file while appending new milestone goals and requirements.

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