The key responsibilities of a VP Product are:

• Defining Product vision and strategy and implementing an execution plan to realize that vision
• Setting up infrastructure to allow the Product team to execute consistently and rapidly
• Aggregating and utilizing customer feedback for Product decisions
• Hiring and managing a team of individual contributors and managers
• Collaborating with management team to achieve company objectives

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Hiring

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How do they create a strong pipeline of candidates and maximize close rates?

• Ownership of the hiring pipeline from end to end, especially closing the candidate
• Good communication skills
• Some articulation of the specific techniques used to close candidates (e.g. team lunches, building empathy, connection with candidate etc.)

Have PMs followed them from company to company?

• How do they think about their time allocation?
• Should account for time allotted to hiring. Product orgs are small, but a leader should view hiring as a continuous, ongoing process and want to be involved.

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Management and Leadership

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What were the keys to working with the management team at their last company?

• As probably the most cross-functional exec in the company outside of the CEO, communication and collaboration are extraordinarily important. Should have a keen understanding of how best to work and build relationships with each functional leader at their last company.
• Communicating clear expectations for what the Product team can and cannot do. Providing clear trade-offs between different alternatives.

How do they communicate something to their team that they disagree with?

• Authenticity. Explanation of why this is important. Not undermining other leaders or departments with their team, but challenging things behind the scenes.

How do they manage up, and how does it compare to how they manage down?

• Looking for a balance between the two. Responsibility for the team they manage, but not friends. Understand the same relationship for their managers.

Can they give an example of a time they had a difficult conversation/issue with an employee and how they handled it?

• Clear communication and concrete milestones.
• Holding the person accountable for meeting those milestones and making the hard call in the case the employee doesn’t succeed.

How do they motivate a team? What have been their most successful strategies for retaining PMs and fostering a strong team culture?

• Looking for empathy
• Creating an environment where it’s safe to fail, and PMs feel supported, cared about, and like management is invested in their growth
• Articulating why their company’s technical, strategic, and business problems are unique and rewarding to solve
• Do they do anything specific or additional to reduce churn?

How have they mentored people in the past? How many mentees do they take on it one time? What do they look for in their mentees?

• 1-2 people at a time. It’s quite a bit of work. Some form of leading that person to water, helping them through the journey and motivating them along the way. Giving them challenges that are just out of their reach to motivate them. Introducing them to others who can help them.
• Have people that worked for them gone on to great things?
• Did they train anyone who went on to lead a Product org, or found a company?

Can they manage across geographies? Have you done so in the past?

• If this is or will be applicable for your role, ask for examples of managing different teams. Candid description of challenges and what they learned from them.

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Product
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What was the state of the product and company in their last role (and/or previous) when they joined? How did they prioritize assessing the company’s challenges and how successfully did they do so?

• Should be extremely easy for them to provide a detailed answer.
• How mature were the product and company? How many customers did they have, headcount, revenue, product lifecycle, etc.?
• They should have been able to impact things substantially, either in growing the business, getting better customer satisfaction, or providing a new direction/strategy. Pay close attention to how they’re qualifying success!
• Assess culture and how it impacted their ability to get problems solved.

Where does the Product role start and end in your mind? Are they more of a tactical operator, or more of a strategic visionary?

• Have they owned engineers, product marketers, roadmap, strategy, pricing, packaging, etc.?
• Have they focused on executing against someone else’s vision, or setting it themselves with others to support them, or some combination? Where do they fit on that spectrum?

What products are you most impressed by or excited about? Why?

• Mostly this is to get a feel for how they think about products. They should provide an insightful perspective on the product they’re dissecting.

Have they launched new products?

• Have them walk through the process from ideation to revenue. How long did it take? How did they get buy-in from leadership or where did the idea come from? How was it received by the market and what challenges did it face? What were its advantages versus the existing market?

Have they had to undergo a major strategic pivot? How did they decide where to pivot to, and how did they execute that?

• Particularly for struggling businesses or companies yet to find product-market fit, someone who has been through a shift like this and can talk through the process of implementing a new strategy will be disproportionately valuable, versus someone who has focused on iterating on an existing one.
• Should include how they gathered data on what was and wasn’t working, market demand, a clear understanding of the capabilities of their business, and details on how they executed the shift.

What’s the biggest product failure they’ve worked on so far? Biggest success?

• What went wrong? What would they have done differently? What did they learn? What would they have done differently, given the opportunity?
• Do they place blame on others or owning their shortcomings? Did it impact the way they did things in the future? How did they decide whether to abandon the product or iterate on it?
• Again, pay attention to how they quantify success.

How involved are they with customers and how does that affect product roadmap?

• A Product leader should always have significant exposure to customers.
• In an enterprise environment, are they meeting with top customers regularly? How does it impact their decisions? What other sources of feedback are significant for them?
• In a velocity or consumer environment, how do they gather feedback from their customers? What tools do they use to apply their learnings to their product roadmap or user experience?
• Who is the end user and the purchaser of their product? How does that impact their involvement or their strategy?
• Concrete examples of roadmap influenced by customer interaction. What strategies do they use to collect and disseminate customer data, and how has that changed their product?

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Cross-functional
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What are the biggest challenges they’ve had with other functions recently?

• Particularly useful when they will need to operate in a complicated or disjointed organization. Need to know specifically what functions they’ve had good and bad relationships with, and why.
• Useful cultural signal. Has lack of buy-in from other leaders led to frustration or their exit at previous companies?

How do they work with the engineering team?

• Valuable insight into their technical depth. Do they have the ability to get in the weeds on the code or architecture? Have they managed engineers themselves? How does this relate to what you need?
• How do you prioritize feature development with the engineering team?

How do they work with the GTM teams?

• Have they managed Product Marketing or pieces of it? Where should the demarcation be between PMs and PMMs?
• How closely are they used to working with the heads of Marketing, Sales, Customer Success and which do they see as the most important relationships? Why?
• What does the feedback loop look like between them, Marketing, Sales, and CS?

How do they work with their CFO?

• They should be working with the CFO or VP Finance on optimizing for the metrics the company is focusing on. Setting the right pricing and packaging depends on their goals, their customer segment, vertical, ACV, contract length, etc.