Hiring a VP of Product? Here are the questions to ask
By: Jen Swanson
Tags: Product Design, Product Management, Digital Transformation, Job Interview, Executive Search

So you’ve decided it’s time to hire a product leader: congratulations! If this is a new role, you may not have a true sense of what qualities, experience, or skills are needed to hire successfully for this critical position. Even if this is a backfill hire, the state of executive talent in the product space has been evolving quickly, and the person you’re hiring now is coming from a very different talent pool than existed even 18–24 months ago. Here are some things to think about and ask a candidate during your interview process.

What you’re looking for

Let’s start with your mindset as the hiring leader. You’ve got a lot of boxes to check here, and it’s important to get your head on straight before you start looking at resumes. Yes, you want to make sure the candidate has the requisite technical and leadership experiences — that’s the easy part to discern from a good resume. Their presence — how they interact with others — is far more critical to the long term success of your product organization.

The Product Leader can (and often does) take the role of contrarian and devil’s advocate on a leadership team. It’s their job to ensure that the work is in service to both the customer needs and the business bottom line. And we all know that executives, founders, and other legacy leaders have their shiny object sticking points that are often based on an “n of 1” (that 1 being themselves or their investor friend that offered up a feature suggestion over cocktails last week)

As the product executive, this new hire’s job will be to maximize opportunities for growth and profit by delivering customer value in the product experience. By definition, this means saying no to building features and products that don’t move the needle in the right direction. This means you’re hiring someone that has to say NO more than they say YES.

Do your best during the interview process to understand how they will fit in with the culture, tone, and tenor of your executive and board teams, as well as that of the broader organization. How will they deliver and manage news that might frustrate, upset, or challenge the status quo? Do they have the right personality to manage those tough conversations with trust, grace, and optimism? Or are they the proverbial “bull in the china shop”? You might need the latter in a turnaround or pivot context, but the former is going to have more staying power in a legacy or high-growth organization.

The interview questions below are designed to help you uncover these harder answers, so make sure you create an interview schedule that allows you and your team to get to know candidates at a deeper level.

Start with Strategy

A successful VP of Product has to not only help the product team execute against strategy, but they also have to manage out, down and up through influence and collaboration. They need to ensure priorities are aligned across engineering, sales and marketing (and finance and operations…..), so focus some questions on their experience and approach to managing in matrixed contexts.

Tell me about a time when you had to lead a strategic shift within the product organization, and how you aligned other teams outside of your direct reporting relationships.

What is your approach to creating alignment and excitement about product strategy within an organization?

How do you help your organization get past the fear of talking to customers? What systems and tools do you think need to be in place to be customer-centric?

How would you describe your product articulation process (product definition, strategy, roadmap, etc)?

Focus on People & Culture

Throughout the interview process, do your best to root out whether or not your candidates truly fit with the stated versus the unspoken culture and dynamic of your organization. Are they really a match for your team size and stage of your company? Don’t rely only on their resume to tell you this — — dig in to see if that enterprise experience was a good fit and if they’re looking to repeat it, or if they learned something about themselves that suggests they are better suited for a smaller growth-stage organization.

Tell me about your management style — for direct reports, as well as those accountable through a matrixed organization.

If you were building a product organization from scratch (which may be the case here), what is your ideal size and composition of the team?

Based on your experience, where do you think product management is optimally situated in the organization? Why? (No deduction of points if the candidate suggests an organizational structure different than yours!)

Tell me about your relationship with sales, customer support, and engineering at your last company.

What have you learned about your leadership style — strengths or weaknesses — and how do you plan to use that insight in your next role?

Can you teach someone to be a good product manager? How?

How do you teach someone to say “no” effectively?

End with Blue Sky

At the end of the day, a VP of product development has to draw on everything they know — industry trends, customer needs, team dynamics, market demands, and whether or not Venus and Mars are in alignment — to set an ambitious yet attainable strategy for the product and the company. Knowing how comfortable and skilled your product leader is in the grey areas of innovation versus the concrete world of agile development will be critical to ensuring your new hire matches expectations for the role across the organization.

Tell me about a time where you’ve had to propose a radical shift in the product strategy (or create one from scratch.) What did you draw on to develop it? Who did you partner with to get buy-in? What ultimately happened with it?

What role do you think storytelling plays in the role of a successful product leader?

How do you stay informed and connected on market trends, new platforms, the evolution of product teams, etc.?

How do you balance insights that come from data against those that come from intuition?

Parting Thoughts

A successful search for an executive role as critical as the VP of Product can often start weeks before you receive your first resume. Taking stock of what your executive team thinks a product leader does or how they function can illuminate gaps in knowledge or expectations that can make or break a new hire’s success in the long term.

As product management becomes more ubiquitous in organizations of all shapes and sizes, the talent pool of senior leaders will grow — but not all Product Managers are suited to ascend to Director and VP roles. Resist the temptation to pluck a productive product-doer and elevate them to leadership roles, as the skillset of building a product and selling a strategic product strategy inside a company are related but very distinct. By focusing on the candidates fit with your executive team’s expectations and the demands of your larger strategy as a company, you’ll increase the likelihood of a successful hire right off the bat.