plan-initiative

Plans multi-milestone initiatives via Socratic interviews with dependency-aware topological sorting.

Updated Jun 2, 2026
One-click install
npx skills add https://github.com/MohamedSayedK/omnigrid --skill plan-initiative-mohamedsayedk
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: plan-initiative
Source: https://github.com/MohamedSayedK/omnigrid/tree/main/assets/core/skills/plan-initiative
Command: npx skills add https://github.com/MohamedSayedK/omnigrid --skill plan-initiative-mohamedsayedk

SYSTEM DOCUMENTATION & REQUIREMENTS

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.

Frequently Asked Questions about plan-initiative

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

FAQPage Schema
How do I plan an initiative with dependencies between milestones?▼

Run /plan-initiative with a kebab-case slug and answer the per-milestone interview, stating what each milestone blocks and is blocked by. The skill builds a dependency DAG, detects cycles, and outputs a topologically sorted sequence with tie-breaks by value and risk.

How do I file milestones as GitHub issues from a planning doc?▼

After the initiative doc is written, the skill offers to file unfiled milestones via gh issue create with a user story, acceptance criteria, and context. A second pass edits each issue to add Blocks and Blocked-by cross-references to the other filed tickets.

What happens when milestone dependencies form a cycle?▼

The skill detects cycles using Kahn's algorithm and prints the cyclic milestones. It asks you to resolve the cycle by removing a dependency, merging milestones, or splitting one — it never auto-breaks cycles.

Can I re-run the planning skill without losing filed ticket links?▼

Yes. Re-runs read the existing initiative doc, match milestones by name, and preserve all Filed as [#N](url) markers. Only unfiled milestones are offered for filing, and each run appends a row to the re-run history table.

Does plan-initiative auto-generate milestones from a goal?▼

No. The skill deliberately avoids auto-decomposition; milestones come from a mandatory Socratic interview where you name each one and define its success criterion and dependencies. Optional questions on value, risk, and kill criteria accept TBD.