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plan-initiative

Convert initiative goals into dependency-aware milestone plans with optional GitHub ticket filing.

489|254|Updated Apr 5, 2026
Search Tags:#milestones#topological sort#dependency graph#initiative planning#product ops#GitHub issue filing#Socratic interview
One-click install
npx skills add https://github.com/me2resh/apexyard --skill plan-initiative
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: plan-initiative
Source: https://github.com/me2resh/apexyard/tree/main/.claude/skills/plan-initiative
Command: npx skills add https://github.com/me2resh/apexyard --skill plan-initiative

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

It turns an initiative-level goal into a concrete, dependency-aware set of milestones and tasks, so operators can sequence work correctly and avoid planning blind spots.

Core Features & Use Cases

  • Initiative-to-milestones decomposition with guardrails: runs a Socratic interview to capture outcome-shaped goal, timeframe, measurable success criteria, and scoped ownership (single project vs framework-wide).
  • Dependency-aware sequencing via a milestone DAG: collects required blocks/blocked-by relationships, detects cycles, and recommends a topo-sorted order using value and risk tie-breaks.
  • Optional ticket filing with cross-references: can create tracker tickets per milestone and then add Blocks / Blocked by cross-refs after issue numbers are known, preserving idempotence on re-runs.

Quick Start

Ask the operator to run: /plan-initiative q3-auth-rewrite, then answer the initiative questions and the per-milestone Socratic prompts to generate the rendered initiative doc and recommended execution sequence.

Frequently Asked Questions about plan-initiative

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

FAQPage Schema
How do I break down an initiative into dependency-aware milestones?▼

Initiative planning uses a Socratic interview to capture goals and ownership scope, then maps milestones into a blocks/blocked-by dependency graph to produce a topologically sorted execution sequence.

How do I sequence milestones when there are circular dependencies?▼

Milestone sequencing detects cycles within the dependency graph and recommends operator-driven resolutions, ensuring the topological sort completes and produces a valid execution order.

How do I file GitHub issues for milestones with cross-references automatically?▼

Issue filing uses a two-pass GitHub creation process to generate tracker tickets per milestone, then backfills Blocks and Blocked by cross-references after issue numbers are known.

Can I use this for quarter planning across a framework-wide project?▼

Quarter planning supports both single-project and framework-wide initiatives, decomposing them into measurable milestones using guided interview questions to capture scoped ownership.

Does re-running milestone generation create duplicate GitHub issues?▼

Re-running the generation process is idempotent, meaning it preserves existing state and prevents duplicate tracker tickets or cross-reference backfilling on subsequent executions.

How does the milestone planner decide execution order when dependencies are equal?▼

The planner applies a value and risk-inverse tie-break mechanism during topological sorting, prioritizing high-value, low-risk milestones when blocks/blocked-by relationships do not enforce strict ordering.

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