We Asked, They Answered - What Top Product Leaders Ask Candidates During Interviews

We asked 10 Product leaders across North America, what questions do they ask when interviewing candidates for a leadership role. The answers might just surprise you.


Question: What is the fundamental role of Product Management in an organization? 

Reasoning: This might seem elementary, but you’d be surprised how often I find that people have wildly different points of view here. I’m looking for a response that focuses on ensuring that the org is delivering that magical intersection of customer value and business value, and some examples of the key practices and mindsets to achieve that, especially deep customer understanding.

Head of Product, Design and Engineering
OpenCare (Formerly: Kijiji)

Question: Tell me about a time when you were wrong.  An experience that you look back on and recognize that you were way-off in your assumption or opinion. 

Reasoning: This helps me see if a person is actually open to learning and if they're defensive or not. Ideal candidates proudly speak about their past mistakes as something that they learned from, with little defensiveness.

Senior VP Growth
GrubHub (Formerly: eBay)

Question: How would you improve a product you use everyday?

Reasoning: I ask this question to start the conversation as it has enough abstract to elicit mindset without crossing the product domain boundary. Interesting answers to this question leads to more natural product functional questions, and starts to unravel the key most riddle: Is this a good personality fit?

VP of Product Management
Pivotree (Formerly: Extreme Network)

Question: What effect did COVID have on your Product Management lifecycle?

Reasoning: I'm looking for an understanding and awareness of mitigation planning.

CityLitics (Formerly: WatrHub)

Question: How do you scale yourself effectively through a team of PMs? 

Reasoning: For leadership roles, I have always focused on three-pronged assessment: Skill, Scale, and Speed. To explain, as a PM lead (Director and above), they should be a good individual contributor PM then be able to scale through a team of PMs by setting the vision for the team, creating an ownership-based org and effectively delegate responsibilities and tasks. Finally, they need to be able to unblock the team through a fast decision-making framework and facilitation of systems/processes for smooth cross-functional agility. 

VP Product and Engineering
Symphony.com (Formlery: Facebook)

Question: Tell me about a time while you were in a leadership position that you had to give a no or strategically reject an idea to someone more senior than you. 

Reasoning: So much of being a good Product leader is prioritizing and if you can’t do that on a regular basis, it’s tough to lead.

Achievers (Formerly: LoyaltyOne)

Question: Given diversity and inclusion is critical to the long term success of any business and technology roles, including product, are often dominated by men and other privileged groups; what concrete actions have you taken in your previous leadership positions to address these issues and build a more inclusive team, particularly for marginalized communities in tech?

Reasoning: This is a really important attribute I look for and ask of any senior leader in technical roles, including product. 

Wattpad (Formerly: Torstar Digital)

Question: What is your approach to find, grow and retain top-tier performers?  Can you give me an example of where you did this well and not so well?  

Reasoning: I believe that being able to find, grow and retain top-tier performers is one of the best signals of a great product leader. This question let's me dive into a candidate's real world experiences doing this successfully and what they learned from doing this poorly.

SVP of Product and Design
Loopio (Formerly: Amazon)

Question: What's your biggest screw-up and what did you learn from it?

Reasoning: Looking for the following attributes, confidence (takes guts to admit you were wrong), risk taker (someone not comfortable with just "honing the stone" on areas that are safe and that they're already familiar with), resilience (having the inner fire to not overly dwell on the mistake, but pick themselves up and move on) and introspection (being able to look deeply within themselves for their role in this and what they could have done differently.)

SVP Product
Conga (Formerly: [24]7)

Question: Do you like people?

Reasoning: No further explanation needed.

Corporate VP Consumer Products AI Platforms & Growth
Verizon (Formerly: Evernote)