roadmap

Analyze an activity brief and generate a waypoint-based roadmap as JSON.

Updated Feb 20, 2026

Search Tags:#planning #roadmap #inbox #project-management #brief #waypoints

Ready to run

npx skills add https://github.com/ryanismert/do-stuff-helper --skill roadmap-ryanismert

💬 Prompt for ChatGPT / Claude Chat▼

Please help me install this Agent Skill.
Skill: roadmap
Source: https://github.com/ryanismert/do-stuff-helper/tree/main/skills/roadmap
Command: npx skills add https://github.com/ryanismert/do-stuff-helper --skill roadmap-ryanismert

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Roadmapping is automated: it reads a brief, analyzes it, and produces a structured, adaptive roadmap stored as JSON with stand-in design stubs for waypoints, including a review waypoint (w0) surfaced to the dashboard inbox for validation.

Core Features & Use Cases

Read an activity brief, conduct expert analysis, and produce an adaptive waypoint-based roadmap autonomously.
The roadmap is stored as a JSON file (source of truth) with individual waypoint design stubs.
A review waypoint (w0) is created and surfaced to the dashboard inbox so the user can validate the roadmap asynchronously.

Quick Start

Locate or create the activity brief, then run the roadmap workflow to generate docs/roadmap-<slug>.json and surface a review task to the inbox.

Frequently Asked Questions about roadmap

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

FAQPage Schema

How do I auto-generate a project roadmap from a brief?▼

To auto-generate a project roadmap from a brief, this Skill reads your activity brief, applies expert analysis, and outputs an adaptive, waypoint-based roadmap stored as a JSON file. It creates a formal roadmap document and surfaces a review waypoint to your inbox for validation.

How does waypoint-based planning work for adaptive roadmaps?▼

Waypoint-based planning structures your adaptive roadmap into distinct stages, creating a formal JSON document with individual design stubs for each waypoint. A review waypoint is automatically surfaced to your dashboard inbox so you can asynchronously validate the proposed project trajectory.

Can I use a brief to plan product and program roadmaps?▼

Yes, you can use an activity brief to plan product, program, and project roadmaps. It conducts expert analysis on your brief and autonomously produces a structured, adaptive roadmap, generating a formal source-of-truth JSON file for your specific planning context.

What is the best way to validate an auto-generated roadmap?▼

The best way to validate an auto-generated roadmap is through the dashboard inbox review workflow. Upon generating the JSON roadmap, the Skill creates a review waypoint surfaced directly to your inbox, enabling asynchronous validation of the proposed project plan.

Do I need an existing activity brief to start project planning?▼

Yes, you need an existing activity brief to start the project planning workflow. The process requires locating or creating a brief, which is then analyzed to autonomously generate the adaptive, waypoint-based roadmap and the corresponding review task.

Why store an adaptive roadmap as a JSON file?▼

Storing an adaptive roadmap as a JSON file provides a structured source of truth for your project planning. This format captures the formal roadmap document and individual waypoint design stubs, enabling automated review workflows and seamless data integration.