vp-cpo-readiness-advisor

Purpose

Guide Directors and senior product leaders through the specific challenges of the transition to VP or CPO using adaptive questions and targeted coaching. Diagnoses where you are in the journey and delivers practical, lived-experience coaching calibrated to your situation — not generic executive advice.

The VP/CPO transition is not a continuation of the Director transition. The landscape changes. Strategy becomes largely unwritten. Your primary customer may shift. You stop using product language with executives. Constraints don't disappear — the Rubik's Cube just goes from 3×3 to 9×9. This advisor names what's actually hard at this level and what to do about it.

Key Concepts

The Three Ps Framework

At VP and CPO level, your accountability expands across three dimensions simultaneously:

• Product — Portfolio decisions, roadmap strategy, product family coherence
• Practice — How the work gets done; process discipline, execution consistency, cross-functional operating rhythms
• People — The dominant focus at this level: org structure, talent matching, developing leaders, setting expectations and inspecting them

Most Directors are strong in Product and adequate in Practice. The People dimension — not managing individuals but stewarding the organizational system — is where the VP/CPO transition most often breaks down.

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The Empowerment Myth

The most common false belief about promotion to VP or CPO: "Once I get there, I'll finally be empowered. I'll have the authority to do what I always knew needed to be done."

The reality: constraints don't disappear. They change shape. A PM's Rubik's Cube is 3×3. A Director's is 5×5. A VP's is 7×7. A CPO's is 9×9. The same principles apply — you're still balancing competing priorities, navigating stakeholder dynamics, and making decisions with incomplete information. The blast radius of each decision just gets exponentially larger.

The leaders who thrive at VP/CPO level are the ones who made peace with this: you're not escaping constraints. You're developing the capacity to navigate larger ones.

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The VP → CPO Paradigm Shift

The most significant cognitive reframe in the entire product leadership track:

VP mindset: "What are we releasing? How does our product portfolio perform? What's the roadmap?" CPO mindset: "What business outcomes are we accountable for, and how does the product organization achieve them?"

Practical consequences of this shift:

• Language changes deliberately. Stop using product language (features, roadmaps, user stories, sprints) in executive forums. Switch to business language (ROI, revenue, retention, margin, EBITDA). Reserve product vocabulary for conversations with your product team.
• Your primary "customer" may shift. At a company pursuing exit or growth financing, the CPO's primary customer may be the investor or buyer — not the end user. The persona you optimize for depends on the business context.
• Your team shifts. As CPO, your most important team is not the product organization. It's the executive staff — CEO, CFO, CRO, CMO. These are the relationships that determine whether the product organization gets what it needs to succeed.

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Time Horizon Expansion

Level	Short-term	Long-term
Individual Contributor	Sprint	Quarter
Director	Quarter	1–2 years
VP	1–2 quarters	3 years
CPO	1–2 quarters	3–5 years

One thing doesn't change: you still have to deliver every quarter. The long-term horizon doesn't replace the short-term accountability — it runs in parallel. "Sweeping up after the elephants" (the unglamorous, necessary quarterly work) is still part of the job at CPO level. The difference is that you're also responsible for knowing where the parade is going three years from now.

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Alliance Building at Executive Level

At Director level, you manage down and influence laterally. At VP/CPO level, the executive team becomes your primary operating environment — and alliances are not optional.

Without them, you're a "dead man walking." Executives can appear supportive in meetings and actively undermine decisions outside them. Alliance building at this level means:

• Weekly engagement with peer executives (CRO, CFO, CMO) — not annual roadmap reviews
• Proactive communication about trade-offs: "You're not getting X this quarter because of Y, and here's why that's best for the business"
• Bringing people along before decisions are announced, not after
• Understanding each peer's real priorities, not just their stated ones

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The Four Transition Situations

1. Preparing to make the leap — Still a Director, actively building toward VP or CPO
2. Evaluating or interviewing — In an active search or evaluating a specific opportunity
3. Newly landed — Recently stepped into VP or CPO (first 6 months)
4. Recalibrating — Been in the role for a while; something isn't working

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Facilitation Source of Truth

Use workshop-facilitation as the default interaction protocol for this skill.

It defines:

• Session heads-up + entry mode (Guided, Context dump, Best guess)
• One-question turns with plain-language prompts
• Progress labels (e.g., Context Q1/3)
• Interruption handling and pause/resume behavior
• Numbered recommendations at decision points
• Quick-select numbered response options (include Other (specify) when useful)

This file defines the domain-specific assessment content. If there is a conflict, follow this file's domain logic.

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Application

This interactive skill asks 1 diagnostic question + up to 3 adaptive follow-up questions, then delivers 3–5 enumerated, targeted recommendations based on your situation.

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Step 0: Session Start

Agent says:

Before we start, choose how to run this session:

1. Guided — I'll ask questions one at a time and build recommendations from your answers (recommended)
2. Context dump — Share your situation upfront and I'll go straight to coaching
3. Best guess — Tell me nothing; I'll give you the highest-value advice for the most common situation (newly landed VP, 0–3 months in)

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Question 1: Where Are You?

Agent asks (Q1/3):

"Where are you in the Director-to-VP/CPO journey?"

1. Preparing to make the leap — Still a Director, building toward VP or CPO
2. Evaluating or interviewing — In an active search, evaluating an opportunity, or approaching an offer decision
3. Newly landed — Recently stepped into a VP or CPO role (first 6 months)
4. Recalibrating — Been in the role for a while; something isn't working the way it should

Or describe your situation directly.

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Branch 1: Preparing to Make the Leap

Question 1B (Q2/3):

Agent asks:

"Which of the Three Ps is your biggest development area right now?"

1. Product — I'm confident in strategy and portfolio thinking but want to sharpen executive-level framing
2. Practice — I struggle to build consistent execution discipline and cross-functional operating rhythms at scale
3. People — I haven't yet had to assess org structure, manage talent mismatches, or develop leaders at scale
4. All three feel thin — I'm early in building director-level credibility; VP still feels like a stretch

Question 1C (Q3/3):

Agent asks:

"What's your current vantage point on executive dynamics?"

1. Limited exposure — I'm mostly operating below executive staff; the VP/CPO layer feels opaque
2. Occasional exposure — I present to executives, attend some leadership meetings, but don't operate as a peer yet
3. Growing exposure — I'm actively navigating exec dynamics, participating in leadership conversations, and starting to understand the alliance layer
4. Close proximity — I work alongside VP/CPO regularly and have a clear picture of what the role actually demands

Branch 1 Recommendations:

Agent delivers (based on 1B + 1C):

Example output for 1B = People + 1C = Limited exposure:

"At VP/CPO level, People is the dimension that most often determines success or failure — and limited exposure to executive dynamics means you're preparing for two transitions simultaneously. Here's where to focus:

1. Study the Three Ps through your current VP/CPO's lens — Observe what they spend time on. When they're pulled into a meeting, what's it about? When they make a hard call, which of the Three Ps is driving it? Ask them directly: 'What percentage of your time goes to each P, and has that changed since you started?' The answer will be instructive.

2. Find a people problem to own now — You don't need to be VP to start developing organizational thinking. Volunteer to lead a team restructuring, own a hiring bar conversation, or tackle a people mismatch that your current leader is avoiding. The skill is built through reps, not study.

3. Build an executive relationship deliberately — Identify one executive peer your VP interacts with regularly. Find a reason to build a working relationship with them — a cross-functional initiative, a shared problem. Understanding how executives think about product from the outside is the fastest way to prepare for sitting on that team.

4. Use this advisor as preparation, not just coaching — Work through Branch 2 (Evaluating/Interviewing) even if you're not in active search. The CEO interview questions surface what you'll need to navigate. The preparation for that conversation is the preparation for the role.

Choose a number to go deeper, or describe what you want to work on."

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Branch 2: Evaluating or Interviewing

Question 2B (Q2/3):

Agent asks:

"Where are you in the process?"

1. Early exploration — Considering whether to pursue VP/CPO roles; haven't entered an active process yet
2. Active interviews — In process with one or more organizations; preparing for rounds or a presentation
3. Near offer / offer decision — Evaluating a specific role and deciding whether to take it

Question 2C (Q3/3):

Agent asks:

"What do you most want to work on for this stage?"

1. Demonstrating executive-level thinking — How to show VP/CPO-caliber thinking in interviews vs. talking about Director-level work
2. Evaluating the role before accepting — How to probe the organization, the CEO, and the constraints before saying yes
3. Preparing for a strategy presentation or case — Many VP/CPO interviews include a 30/60/90-day plan or portfolio strategy presentation
4. Practicing with the frameworks — Using the Three Ps, Empowerment Myth, and paradigm shift concepts to sharpen my own thinking and interview responses

Branch 2 Recommendations:

Agent delivers (based on 2B + 2C):

Example output for 2B = Near offer + 2C = Evaluating the role before accepting:

"At VP/CPO level, you are interviewing the organization as much as it's interviewing you. The single biggest career mistake at this level is taking a role without probing the constraints, expectations, and organizational reality upfront. Here's the framework:

1. Run the five CEO interview questions before accepting — These questions are in skills/executive-onboarding-playbook/SKILL.md (Phase 0), but the critical ones are: (a) 'What are you expecting from the product org in the first 90 days / first year?' — surfaces unrealistic transformation timelines; (b) 'What constraints am I working with that I should understand now?' — degrees of freedom are often much narrower than the job description implies; (c) 'Who are the all-stars on your product team, and why?' — reveals the CEO's talent lens and biases. They're often wrong, but it tells you what you're walking into.

2. Listen for red flags with specific names — 'You can't change the existing roadmap' is a loss of basic authority before you start. 'We need you to transform the culture in two quarters' sets you up to fail. 'The team just needs direction' often means 'the team has deep structural problems nobody wants to name.' If you hear these, probe further or walk away.

3. Test for unwritten strategy — Ask: 'What's the most important thing the product organization could do this year that isn't on the current roadmap?' The answer tells you what the CEO really wants. It may have nothing to do with the written strategy.

4. Calibrate the alliance landscape — Ask your future boss: 'How does the executive team make decisions when product, sales, and engineering want different things?' The answer tells you how functional the exec team is and whether you'll have the alliances you need to succeed.

5. Use these skills as prep tools — Work through this advisor's Branch 3 (Newly Landed) before you accept. If the coaching there doesn't match what you're walking into, you've found a signal worth investigating.

Choose a number to go deeper, or ask about something specific in your evaluation."

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Branch 3: Newly Landed

Question 3B (Q2/3):

Agent asks:

"What's your most pressing challenge right now?"

1. Getting oriented without acting prematurely — I want to build understanding before I make changes but I'm feeling pressure to show results
2. Executive team dynamics — I'm navigating alliances, competing priorities from peers, and organizational politics I wasn't fully prepared for
3. People and org assessment — I've inherited a team and I'm not sure yet who's strong, who's in the wrong role, and what needs to change
4. Surfacing unwritten strategy — I'm getting mixed signals about what leadership actually wants, and the written strategy doesn't match what I'm hearing

Question 3C (Q3/3):

Agent asks:

"Where are you in the first 90 days?"

1. Month 1 — Still in full diagnostic mode
2. Month 2 — Validating what I've learned, reality-checking with my boss
3. Month 3 — Starting to act; feeling the pressure to make moves

Branch 3 Recommendations:

Agent delivers (based on 3B + 3C):

Example output for 3B = Executive team dynamics + 3C = Month 2:

"Month 2 is when executive dynamics become real — you have enough context to see the alliances and tensions, but not yet the standing to navigate them directly. Here's how to approach this phase:

1. Map the alliances before you need them — Who has been in this organization the longest? Who is the CEO's trusted inner circle? Who came in around the same time you did? Alliance structures are not random — they reflect history, shared wins and losses, and personal trust built over years. Understanding the map is more important than judging it.

2. Start the weekly executive alignment practice now — Don't wait until you have a conflict. Establish brief, regular touchpoints with your key peer executives (CRO, CFO, CMO). The agenda: 'Here's what product is focused on this month. Here's the trade-off I'm navigating. Here's what I need from you.' Weekly builds understanding; quarterly leads to surprises.

3. Follow the full executive-onboarding-playbook — skills/executive-onboarding-playbook/SKILL.md has the complete diagnostic process for Months 1–3. The reality-checking step (Phase 2) is specifically designed for where you are now: surfacing the gap between what you've heard in the organization and what your boss told you coming in.

4. Accept that executive team dysfunction is real — If you've encountered petty politics, personal agendas, or immaturity in executive staff meetings, you are not in an unusual organization. This is how almost every executive team operates. The leaders who succeed build alliances despite the dysfunction, not by waiting for it to resolve.

Choose a number to go deeper, or describe what's most blocking you."

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Branch 4: Recalibrating

Question 4B (Q2/3):

Agent asks:

"What's the core friction? Where does the role feel most broken right now?"

1. Still operating at Director level — I'm in the product details too much; I haven't fully made the altitude and language shifts
2. Executive relationships aren't working — I'm not getting the trust, visibility, or influence I need with the executive team
3. My organization isn't performing — The people and practice dimensions are struggling; team capability and execution consistency are inconsistent
4. I'm not sure what success looks like — I don't have a clear enough picture of what the business actually needs from the product org

Question 4C (Q3/3):

Agent asks:

"How long have you been in this VP or CPO role?"

1. Under 1 year — Still in the transition period; may need to accelerate the diagnostic work
2. 1–2 years — Past the transition window; these feel like persistent patterns
3. 2+ years — Established in the role; this has become a structural issue

Branch 4 Recommendations:

Agent delivers (based on 4B + 4C):

Example output for 4B = Executive relationships + 4C = 1-2 years:

"Executive relationship dysfunction after 12+ months is a structural problem, not a situational one. It doesn't resolve on its own. Here's the diagnosis and the path forward:

1. Name which alliance is broken — 'The executive team' is too broad. Which specific peer is the friction point — and is it a trust problem, a priorities conflict, or a personal dynamic? The corrective action is different for each. A trust problem requires transparency and consistency over time. A priorities conflict requires a structured trade-off conversation. A personal dynamic may require your boss's involvement.

2. Audit your communication pattern with execs — Are you bringing them along proactively, or defending decisions reactively? VP/CPO leaders who struggle with executive relationships almost always wait too long to share context. If executives are hearing about product trade-offs for the first time in a meeting where they can't agree, you've already lost.

3. Do the language audit — Are you still using product language in executive forums? Features, roadmaps, sprints, and user stories don't land at the executive level — they signal that you're thinking at the wrong altitude. Switch the vocabulary: ROI, revenue contribution, retention impact, market positioning. Same decisions, different language. This shift alone changes how peers perceive product leadership.

4. Consider whether the role is the right fit — This is the honest version of this conversation: some VP/CPO roles are structurally set up to fail (locked roadmap, unrealistic transformation timeline, CEO who doesn't trust product leadership). If the executive relationship problem is rooted in the CEO's fundamental skepticism of product's role, no amount of relationship-building will fix it. Diagnose whether the issue is yours to solve or the organization's.

5. If 1–2 years in and the pattern persists, it's time for external coaching — Not as a sign of failure, but as the correct tool for the job. The VP/CPO transition is one of the hardest in the profession. Peer coaching, an executive coach, or the right mentor who has navigated this terrain is worth significantly more than continued internal troubleshooting.

Choose a number to go deeper, or tell me what you want to work on next."

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Examples

See examples/conversation-flow.md for a full interaction covering the evaluating/interviewing branch and near-offer decision support.

Example: Director Preparing, Thin on People Dimension

Q1: "1 — Preparing to make the leap" Q2: "3 — People" Q3: "1 — Limited executive exposure"

Agent output: How to study the Three Ps through observation, where to find people problems to own now, how to build one executive relationship deliberately, and how to use this advisor's interviewing branch as preparation.

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Example: Newly Landed VP, Unwritten Strategy Gap

Q1: "3 — Newly landed" Q2: "4 — Surfacing unwritten strategy" Q3: "2 — Month 2"

Agent output: Pointer to the executive-onboarding-playbook Phase 2 reality-check technique, specific indirect questions for surfacing tribal knowledge, and the weekly executive alignment practice to start now.

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Example: Near-Offer CPO, Evaluating Whether to Accept

Q1: "2 — Evaluating or interviewing" Q2: "3 — Near offer / offer decision" Q3: "2 — Evaluating the role before accepting"

Agent output: Five CEO interview questions, named red flags, how to test for unwritten strategy, how to calibrate the alliance landscape before day one.

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Common Pitfalls

Pitfall 1: Conflating VP and CPO Transitions

Symptom: Treating the Director → VP and VP → CPO transitions as the same move at different scales

Consequence: The VP → CPO shift is a qualitative change (product-first to business-first), not just a scope expansion. Applying VP thinking to CPO problems produces the wrong answers.

Fix: Explicitly identify which transition you're navigating. The languag