Agent skill · Design & Presentation

executive-onboarding-playbook

Plan a VP or CPO 30-60-90 day diagnostic onboarding path. Use when entering a new executive product role and avoiding premature change.

deanpetersgithub.com/deanpetersGitHub ↗
claude-codeNOASSERTION
Install
npx skills add deanpeters/Product-Manager-Skills --skill executive-onboarding-playbook --agent claude-code

Same command for any agent — swap --agent for codex, cursor, copilot.

Facts
Files in the skill folder: 2
SKILL.md size: 19 KB
Bundled scripts: none
Path: skills/executive-onboarding-playbook/SKILL.md
Open the folder on GitHub →
Where it comes from
Stars: 6,255
Language: Shell
Read our review of the source →

Weekly change comes from our own snapshots, not the repository page — it measures attention, not adoption.

Review
written from the skill's own SKILL.md · Aug 5, 2026

What it does

Plans a VP or CPO 30-60-90 day diagnostic onboarding path, structured as a three-phase process (Diagnose in Month 1, Validate in Month 2, Act with Evidence in Month 3). It emphasizes observing before diagnosing, asking questions before making declarations, surfacing unwritten strategy, and building a body of evidence from diagnostic conversations to guide decisions in Month 3. The playbook outlines concrete steps for Phase 1 interviews, Phase 2 reality checks, and Phase 3 sharing findings, implementing context maps, and starting executive alignment.

How it works

  • It guides the user to treat the role as an external consultant assessing the organization before making changes. It prescribes interviewing direct reports and cross-functional peers, taking detailed notes, letting information come to you, and resisting action in Month 1.
  • It instructs mapping unwritten strategy by asking targeted questions and surfacing hidden priorities and constraints.
  • It defines Phase 2 steps: reality-checks with the boss, mapping unwritten strategy, completing a people assessment, and identifying 3-5 high-leverage changes.
  • It defines Phase 3 steps: sharing the organizational assessment with key stakeholders, running a Cascading Context Map, continuing people conversations, and building executive alliance via regular alignment with CRO, CFO, and CMO. It references related techniques in other SKILLs for the context map and alliance.

When to use it

Use when entering a new executive product role (VP or CPO) to avoid premature change. It is framed for the first 90 days with the goal of diagnostics and evidence-based decisions rather than quick execution.

What it can touch

This skill directs the user to conduct interviews, take notes, map unwritten strategy, perform reality checks with a manager, and communicate findings. It mentions creating documents like a detailed notebook and delivering an interpreted organizational assessment, but does not specify external tools beyond referencing related SKILLs for context mapping and alliance building.

Caveats

The material emphasizes that skipping phases guarantees reversals and that one should not act on incomplete understanding. It positions the Month 1 learning phase as essential and cautions against making broad transformations before evidence. License information is NOASSERTION.

From the SKILL.md

## 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. **Arriv

What's inside
Steps it walks through
  1. Purpose
  2. Input
  3. Key Concepts
  4. The Consultant Mindset
  5. Unwritten Strategy
  6. The Body of Evidence
  7. People Assessment: Two Categories
  8. Phase 0: Before Day 1
  9. Application
  10. Phase 1: Diagnose (Month 1)
  11. Phase 2: Validate (Month 2)
  12. Phase 3: Act with Evidence (Month 3)
  13. Examples
  14. Good: Consultant Mindset Preventing a Costly Mistake
Ships with 1 file
  • examples/sample.md
More from Product-Manager-Skills
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About this skill
What does the executive-onboarding-playbook skill do?

Plan a VP or CPO 30-60-90 day diagnostic onboarding path. Use when entering a new executive product role and avoiding premature change.

How do I install it?

Run `npx skills add deanpeters/Product-Manager-Skills --skill executive-onboarding-playbook --agent claude-code` — it drops the skill into your project so the agent can pick it up. Swap the --agent value for codex, cursor or copilot if you use one of those.

Where does this skill come from?

From deanpeters/Product-Manager-Skills, a repository with 6,255 stars. We read it straight from the repository tree rather than a submitted listing, so what you see here is what is actually published.

Is a popular skill a good skill?

Not necessarily. Stars measure attention, not adoption — a repository can trend for a week and be abandoned. That is why we show the weekly change from our own snapshots next to the total, instead of a single flattering number.

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