One-click install
npx skills add https://github.com/sicktastic/skill-issue --skill executive-onboarding-playbook-sicktastic
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: executive-onboarding-playbook
Source: https://github.com/sicktastic/skill-issue/tree/main/product-management/executive-onboarding-playbook
Command: npx skills add https://github.com/sicktastic/skill-issue --skill executive-onboarding-playbook-sicktastic

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Senior product leaders often jump into action during a new VP or CPO transition and trigger expensive reversals because they lack a structured diagnostic process; this playbook enforces patience, learning, and evidence before decisive changes.

Core Features & Use Cases

  • Phase-based flow: Month 1 focuses on diagnosing reality, Month 2 validates patterns with leadership, and Month 3 acts with the body of evidence you have collected.
  • People and strategy intelligence: Gather insights on unwritten strategy, identify diamonds in the rough versus role mismatches, and surface executive dysfunction risk factors before acting.
  • Use Case: Apply this when accepting a VP offer to ask the right CEO questions, evaluate cultural dynamics, and plan the first quarter without premature structural moves.

Quick Start

Run the executive onboarding playbook to map Month 1 diagnostics, Month 2 validation, and Month 3 action for a new VP or CPO.

Frequently Asked Questions about executive-onboarding-playbook

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I structure an executive onboarding plan for a new VP of Product transition?

An executive onboarding plan structures your first 90 days as a diagnostic process: Month 1 maps organizational reality through interviews, Month 2 validates patterns with leadership, and Month 3 acts on evidence-backed recommendations rather than premature execution.

What is the best way to assess organizational dynamics before making structural changes as a new CPO?

Assess organizational dynamics by conducting interviews, triangulating behavioral patterns, and validating hypotheses with existing leadership. This evidence-based approach surfaces unwritten strategy, identifies talent mismatches, and reveals executive dysfunction risks before you commit to high-leverage changes.

Why do product leaders fail during a 90-day transition into a new organization?

Product leaders fail during a 90-day transition by jumping into a premature execution sprint without a structured diagnostic process. Acting before mapping unwritten strategy and people dynamics triggers expensive structural reversals that damage leadership credibility.

Can I use a diagnostic transition plan when accepting a VP offer to evaluate company culture?

Yes, you can apply a diagnostic transition plan when accepting a VP offer to ask the right CEO questions, evaluate cultural dynamics, and map organizational reality. This prepares you to plan your first quarter without making premature structural moves.

What should I focus on during the first 30 days of an executive product leadership role?

During the first 30 days of an executive product leadership role, focus on diagnosing reality. Gather intelligence on unwritten strategy, identify diamonds in the rough versus role mismatches, and surface executive dysfunction risk factors through structured interviews and pattern triangulation.

When should I avoid making immediate structural changes as a new product executive?

You should avoid immediate structural changes when you lack a validated body of evidence. Without completing interview-based diagnostics and leadership validation phases, acting on assumptions risks expensive reversals and disrupts existing organizational dynamics.