# Executive Onboarding Playbook Example (30-60-90)

This example shows how a newly hired VP Product applies the playbook across the first 90 days.

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## Context

- Company: B2B SaaS, Series B
- Role: VP Product (first product executive hire)
- Situation: Fast growth, noisy roadmap, unclear ownership between Product and Sales

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## Phase 0 (Before Day 1): Pre-Entry Checks

### Inputs gathered before accepting

- CEO expectations for first 90 days
- Existing roadmap constraints and non-negotiables
- Initial read on leadership team dynamics
- Why the previous product leader left

### Risk signals identified

- CEO asks for "quick transformation" in first 30 days
- CRO expects immediate roadmap commitments to close deals

### Decision

Accept role with explicit alignment:
- First 30 days are diagnostic.
- Major org or process changes come after evidence review.

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## Phase 1 (Month 1): Diagnose

### Actions

1. 30 interviews across executives, PMs, engineering leads, and GTM partners.
2. Document recurring themes and contradictions.
3. Observe decision-making rituals (staff meetings, roadmap reviews, deal escalations).

### Pattern signals

- Stated strategy: "Move upmarket."
- Unwritten strategy: close one reference enterprise logo in Q2.
- People reality:
  - one PM is under-leveraged but strong in discovery
  - one PM is in a role mismatch (execution-heavy role, poor stakeholder management)

### Month 1 output artifact

**Organizational Assessment Memo:**
- top 5 strengths
- top 5 failure risks
- assumptions requiring validation in Month 2

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## Phase 2 (Month 2): Validate

### Actions

1. Reality-check findings with CEO, CRO, CFO, CTO.
2. Test whether themes hold across independent data sources.
3. Pressure-test people assessments with observed outcomes, not hearsay.

### Validation outcomes

- Enterprise reference-customer strategy confirmed by CEO and CRO.
- Current roadmap over-invests in low-impact requests from loud internal stakeholders.
- PM role mismatch confirmed by repeated cross-functional friction patterns.

### Month 2 output artifact

**Validated Hypotheses Deck:**
- what is true
- what remains uncertain
- what decisions can now be made with confidence

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## Phase 3 (Month 3): Act with Evidence

### Actions

1. Publish first Cascading Context Map for product org.
2. Rebalance roadmap to support enterprise reference-customer motion.
3. Start people decisions:
- promote under-leveraged PM into a strategic initiative
- move mismatch PM into a role better aligned to strengths
4. Establish weekly executive alignment cadence with CRO, CFO, CMO.

### Results by Day 90

- Product org has clear priorities tied to business outcomes.
- Executive peers understand product trade-offs earlier, with fewer late surprises.
- People changes underway with clear rationale and lower political friction.

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## Anti-Pattern Contrast

### What would have failed

- Announcing org redesign in Week 2.
- Standardizing all team artifacts before understanding why variation exists.
- Taking executive narratives at face value without cross-checking.

### Why the playbook prevented this

- Diagnose first, validate second, act third.
- Evidence precedes visible change.
- Leadership credibility built through clarity and consistency.
