How does it integrate with my existing project?

It reads and updates your project's roadmap JSON, creates design markdown files in your docs directory, and maintains a chronological log of design decisions in your changelog.

How does the skill determine the level of detail needed?

It evaluates the waypoint based on four dimensions: ambiguity, scope, novelty, and risk. High-risk or novel tasks receive detailed architectural docs, while simple tasks get minimal implementation notes.

Can this skill write code directly?

No, this skill focuses on the design and planning phase. However, it can detect if a task is a software build and delegate the implementation to specialized coding skills.

What is a 'waypoint' in this skill?

A waypoint is a specific milestone or step in your project roadmap that represents a single unit of value but requires further detail before it can be executed.

Waypoint Design & Planning

Name: Waypoint Design & Planning
Author: ryanismert

byryanismert

0•

Productivity & Workflow

Transforms high-level project milestones into actionable, detailed design documents scaled to implementation complexity.

The Waypoint Design skill bridges the gap between high-level project roadmaps and executable tasks by generating structured design documentation. It intelligently assesses the ambiguity, scope, and risk of a project 'waypoint' to produce an appropriately scaled technical specification—ranging from a few sentences for simple tasks to full architectural breakdowns for complex features. It includes built-in heuristics for software-build detection, ensuring technical tasks are properly delegated while maintaining rigorous standards for acceptance criteria and decomposability.

Key Features

01Automated software-build detection and delegation logic

02Adaptive documentation scaling based on task complexity

030 GitHub stars

04Acceptance criteria (Done When) and risk assessment generation

05Research-driven technical decision making for novel requirements

06Seamless integration with roadmap JSON files and project changelogs

Use Cases

01Fleshing out a vague project milestone into a concrete technical specification

02Standardizing design documents for a team before decomposing tasks

03Automating the transition from a project roadmap to an executable implementation plan

What are Skills?·How to Install

Install with 🐟 Skill.Fish

npx skillfish add ryanismert/do-stuff-helper waypoint-design

For use in Claude.ai and ChatGPT

Key Features

01Automated software-build detection and delegation logic

02Adaptive documentation scaling based on task complexity

030 GitHub stars

04Acceptance criteria (Done When) and risk assessment generation

05Research-driven technical decision making for novel requirements

06Seamless integration with roadmap JSON files and project changelogs

Use Cases

01Fleshing out a vague project milestone into a concrete technical specification

02Standardizing design documents for a team before decomposing tasks

03Automating the transition from a project roadmap to an executable implementation plan

What are Skills?·How to Install

Install with 🐟 Skill.Fish

npx skillfish add ryanismert/do-stuff-helper waypoint-design

For use in Claude.ai and ChatGPT