Agent skill · product strategy · deanpeters
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.
Why this skill is useful
Provides a structured diagnostic onboarding process for new VPs or CPOs that the AI wouldn't reliably generate on its own.
What it needs
About 12k tokens when loaded. Last updated 2026-07-17. 6,302 stars on the source repository.
What this skill does
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. Arriving empty-handed? That works too. The playbook opens by asking your start date and company context, then anchors you in the right phase. Example invocation: I start as VP Product at a 300-person Series C in 3 weeks — first product exec hire, founder currently runs product. Build my 30-60-90. Key Concepts The Consultant Mindset Enter every new VP/CPO role as if you're an external consultant hired to assess the organization — before you're the person responsible for changing it. What this means in practice: Observe before diagnosing. Don't form opinions in the first week based on first impressions. Ask questions before making declarations. "Help me understand how this works" is more powerful than "here's what we're going to do differently." Understand how the steering connects to the rudder. …
How to use it
Reference it in AdaL, Claude Code, Cursor or any coding agent — nothing to install:
@skills deanpeters/executive-onboarding-playbook