Executive Onboarding Playbook

Takes the standard 30-60-90 day executive onboarding format and structures it explicitly as a diagnostic protocol, not an action plan. The insight here is simple: most new VPs and CPOs fail by acting too early, changing org structures or strategy before they've built the evidence base to make those decisions stick. It walks you through three phases (diagnose, validate, act with evidence) and emphasizes treating your first month like you're a consultant assessing the organization, not the person already responsible for fixing it. Includes concrete interview questions for your hiring CEO and a framework for surfacing unwritten strategy that lives in people's heads, not documents. Best used when you're actually starting a new role, not theorizing about leadership.

skills.sh installs: 2.6K
GitHub stars: 7.9K
last updated: Aug 21, 2026

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Install

$ npx -y skills add deanpeters/product-manager-skills --skill executive-onboarding-playbook --agent claude-code

Installs into .claude/skills of the current project.

Files

Purpose

Structure the first 90 days of a VP or CPO transition as a diagnostic process, not an execution sprint. The single most common failure in senior product leadership transitions is acting before understanding — changing structures, replacing people, or announcing strategy before building the evidence base that makes those decisions defensible.

This playbook runs in three phases: Diagnose (Month 1), Validate (Month 2), Act with Evidence (Month 3). Each phase builds on the last. Skipping phases doesn't accelerate results — it guarantees expensive reversals.

This is not a 100-day plan for impressing your new boss. It's a diagnostic protocol for making durable decisions.

Input

Works best with: The role you're stepping into (VP or CPO) and basic company context — size, stage, how the product org is set up. Also useful: How far you are from Day 1 (offer stage, pre-start, week 3), known landmines, and what the CEO says success looks like.

Anything supplied with the invocation itself — text after the skill name, a pasted context dump, or an appended ARGUMENTS: line — counts as answers already given. Use it and skip whatever it covers; don't re-ask.

SKILL.md on GitHub

Details

Repository: github.com/deanpeters/product-manager-skills
Category: Productivity & Planning
First seen: Apr 16, 2026