executive-onboarding-playbook

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.