What problem does it solve? Breaking a quarter-scale initiative into ordered, dependency-aware milestones is error-prone when done ad hoc — dependencies get missed, cycles creep in, and filing tracker tickets by hand loses cross-references. This Skill structures that planning into a repeatable interview-driven workflow. ## Core Features & Use Cases - Socratic milestone interview: Captures goal, success criteria, blocks/blocked-by relationships, plus optional kill criteria, value, risk, and confidence per milestone. - Dependency DAG with cycle detection: Builds a graph from the interview answers, detects cycles via Kahn's algorithm, and produces a topological sequence with value × risk-inverse tie-breaking. - Two-pass tracker filing: Files accepted milestones as GitHub issues via gh issue create, then edits each issue to add Blocks/Blocked-by cross-references, preserving filing markers across re-runs. - Use Case: A solo builder planning a Q3 auth rewrite runs the skill with a slug, answers the milestone interview, gets a Mermaid DAG and ordered plan written to omnigrid-docs/initiatives/, and files three of five milestones as cross-linked GitHub issues. ## Quick Start Run /plan-initiative with a kebab-case slug like q3-auth-rewrite and answer the milestone interview questions to generate the initiative doc and optionally file tickets.