Executive Onboarding Template
Five worksheets, one per phase: the pre-acceptance interview, the evidence log, validation, the assessment you share, and the 90-day review. Quality checks at the bottom.
Provenance
Based on The Product Porch E43 — Becoming a VP/CPO.
Phase 0: Before Day 1 — interview the organization
Fill this in before you accept. It is cheaper to decline than to discover.
## Role Diligence: [Company] — [Date]
### The five questions
**1. What are you expecting from product in the first 90 days? The first year?**
- Answer: [what they said]
- Read: [realistic / unrealistic — and why]
**2. Who are the all-stars on your product team, and why?**
- Answer:
- Read: [what this reveals about the CEO's mental model, accurate or not]
**3. Who has gaps, and why?**
- Answer:
- Read: [is this an accurate diagnosis or a symptom being blamed on a person?]
**4. What constraints should I understand upfront?**
- Answer: [financial, organizational, market]
- Read: [my actual degrees of freedom]
**5. What does success look like at one year?**
- Answer:
- Read: [specific = workable. Vague = red flag.]
### Red flags present
- [ ] "You can't change the existing roadmap" — authority gone before you start
- [ ] "Transform the organization in six months" — engineered to fail
- [ ] CEO's talent assessment contradicts what you heard elsewhere
- [ ] Success defined only in vague culture terms
### Verdict
**Take it / Negotiate / Decline:** [call]
**What I'd need changed to say yes:** [specific]Phase 1: Diagnose (Month 1) — the evidence log
Objective: understand reality, not the official version. Resist action.
## Evidence Log — Month 1
### Conversations held
| Date | Who | Role | Their likely incentive |
|---|---|---|---|
| | | | |
Ask everyone the same four:
- What's working that I should understand and protect?
- What's not working that you've hoped someone would fix?
- What do I need to know that I won't hear in official briefings?
- Who else should I talk to?
### Who found me
[People who proactively booked time. Note the agenda AND the fact that
they came — both are signal.]
### Patterns (heard from 3+ independent sources)
- [pattern] — sources: [who]
### Single-source strong opinions (hold loosely)
- [claim] — source: [who], possible incentive: [what]
### Things I want to fix right now — NOT ACTING YET
| What | Why it looks broken | What I don't yet know |
|---|---|---|
| | | [why it's broken, whether it was tried, what it connects to] |Deliverable: a detailed notebook of organizational reality, not yet interpreted.
Phase 2: Validate (Month 2)
## Validation — Month 2
### Hypotheses from Month 1, now tested
| Hypothesis | How I tested it | Held / Broke | Revised understanding |
|---|---|---|---|
### Unwritten strategy
[What the organization actually optimizes for, as revealed by where
money, headcount, and executive attention go — versus what the stated
strategy says. Name the gap.]
### People assessment
**Diamonds in the rough** — capable, underused, wrong scope
| Person | Evidence | What I'd change |
**Wrong role** — capable person, bad fit for this seat
| Person | Evidence | Options |
### Still unknown
[What I have not been able to verify, and what it would take.]Phase 3: Act with Evidence (Month 3)
## Organizational Assessment — [Date]
### What's strong (protect this)
- [finding + evidence]
### What needs to develop
- [finding + evidence]
### The unwritten strategy, named
[Stated strategy vs. revealed priorities, and which one I'm planning against.]
### Direction for next quarter
[Your Cascading Context Map — see skills/altitude-horizon-framework.
Give your team your best current translation even if strategy above you
is still ambiguous.]
### Changes underway (3-5, not 20)
| Change | Rationale from evidence | Owner | Visible by |
|---|---|---|---|
### People conversations scheduled
| Person | Conversation type | When |
|---|---|---|
### Executive alliance cadence
| Peer | What they need from product | Cadence |
|---|---|---|
| CRO | | weekly |
| CFO | | |
| CMO | | |The 90-day review
## 90-Day Self-Review
- Did I resist acting in Month 1? [honestly]
- Which Month-1 "obvious problem" turned out to be more complicated? [there is always one]
- What did I learn that I would have gotten wrong on day 3?
- Where did I perform action instead of building evidence?
- What does my team now know that they didn't 90 days ago?Quality checks
Phase 0
- Filled in before accepting, not after
- Vague success criteria were pushed on until specific, or logged as a red flag
- You wrote down what you'd need changed to say yes
Phase 1
- Every conversation logged with who, what, and their likely incentive
- Patterns are separated from single-source strong opinions
- The "want to fix" list exists and nothing on it was acted on
- People who sought you out are noted as signal, not just as meetings
Phase 2
- Hypotheses were actually tested, not just restated with more confidence
- Unwritten strategy names the gap between stated and revealed priorities
- People assessments cite evidence, not impressions
Phase 3
- The assessment was shared, not kept private — that's what builds trust and surfaces disagreement before you act
- Three to five changes, not twenty
- Every change traces to evidence from Months 1-2
- Hard people conversations are scheduled, not deferred
The honest test
- You can name something you believed on day 3 that turned out to be wrong. If not, you probably weren't diagnosing — you were confirming.