executive-onboarding-playbook

SKILL.md

Diagnostic onboarding protocol for VP and CPO transitions, structured as three phases of learning before action.

Phases 1-2 (Months 1-2) focus on building an evidence base through interviews, pattern-matching, and reality-checking with your manager before making decisions

Phase 3 (Month 3) begins acting on evidence: sharing your organizational assessment, establishing strategic direction, and addressing people situations with clear rationale

Emphasizes the consultant mindset—observe before diagnosing, understand unwritten strategy and tribal knowledge, and map both diamonds in the rough and people in wrong roles

Includes pre-acceptance evaluation questions to surface unrealistic expectations, constraints, and misaligned talent assessments before you commit to the role

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.

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. In any organization, there are systems and relationships that look one way on paper and work completely differently in practice. Map that reality before you touch anything.

Don't throw the big red switch. If you walked into a power plant you'd never operated before and saw a large red switch, you probably wouldn't throw it. The same logic applies to org structures, processes, reporting lines, and team compositions you've inherited. Understand what they control first.