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As we kick off 2025, many companies are laser-focused on building their 2025 product roadmap and hiring Product Managers to help them achieve their goals.
To help candidates navigate the interview process and stand out, we teamed up with The Product Recruiter to uncover; what today’s product leaders are asking in interviews—and what they’re looking for in a great answer.
Whether you’re a seasoned PM or just starting your product management journey, these questions offer a blueprint for preparation and self-reflection. Here’s what top product leaders had to say:
1. What is the fundamental role of Product Management in an organization?
This might seem elementary, but you’d be surprised how often people have wildly different points of view here. I’m looking for a response that focuses on ensuring the organization is delivering that magical intersection of customer value and business value, with examples of the key practices and mindsets to achieve that, especially deep customer understanding.— Cameron Moore, VP of Product at Dialogue (Formerly: OpenCare & Kijiji)
2. How would you improve a product you use every day?
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 lead to more natural product functional questions and start to unravel the key riddle: Is this a good personality fit?— Mike Leibovitz, Senior Research Director at Gartner (Formerly: Pivotree & Extreme Network)
3. 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.
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 they learned from, with little defensiveness.— Alex Weinstein, Chief Digital Officer at Hungryroot (Formerly: GrubHub & eBay)
4. What’s your biggest screw-up and what did you learn from it?
I look for the following attributes:
— Eric Carrasquilla, EVP & Division President at CSG (Formerly: Conga & [24]7)
5. What effect did COVID have on your Product Management lifecycle?
I’m looking for an understanding and awareness of mitigation planning.— Sunit Mohindroo, CPO, CityLitics
6. How do you scale yourself effectively through a team of PMs?
For management roles, I have always focused on a three-pronged assessment: Skill, Scale, and Speed. As a PM lead, they should be a good individual contributor, then be able to scale through a team by setting the vision, creating an ownership-based org, and effectively delegating responsibilities. Finally, they need to unblock the team through fast decision-making and facilitation of systems/processes for smooth cross-functional agility.— Manish Sharma, Investor (Formerly: Symphony & Facebook)
7. What is your approach to finding, growing, and retaining top-tier performers? Can you give me an example of where you did this well and not so well?
Being able to find, grow, and retain top-tier performers is one of the best signals of a great product leader. This question lets me dive into a candidate’s real-world experiences of doing this successfully and what they learned from doing this poorly.— Justin Dilley, Senior Director of Product Management at Axon (Formerly: Loopio & Amazon)
8. 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.
So much of being a good PM is prioritizing, and if you can’t do that regularly, it’s tough to lead.— Michael Cohen, CPO, Achievers (Formerly: LoyaltyOne)
9. Given diversity and inclusion are 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?
This is a really important attribute I look for and ask of any senior leader in technical roles, including product.— Seema Lakhani, CPO, Wattpad (Formerly: Torstar Digital)
10. Do you like people?
No further explanation needed.
— Marco Di Giacomo, EVP & CMO at Amagi Corporation (Formerly: Verizon & Evernote)
These questions are designed to reveal not just your skills but also your mindset, adaptability, and leadership qualities. Preparing thoughtful, introspective answers can help you make a strong impression in your next interview.
Looking to stand out even more? Check out our top 5 interview preparation tips to elevate your responses and land your dream PM role
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As we kick off 2025, many companies are laser-focused on building their 2025 product roadmap and hiring Product Managers to help them achieve their goals.
To help candidates navigate the interview process and stand out, we teamed up with The Product Recruiter to uncover; what today’s product leaders are asking in interviews—and what they’re looking for in a great answer.
Whether you’re a seasoned PM or just starting your product management journey, these questions offer a blueprint for preparation and self-reflection. Here’s what top product leaders had to say:
1. What is the fundamental role of Product Management in an organization?
This might seem elementary, but you’d be surprised how often people have wildly different points of view here. I’m looking for a response that focuses on ensuring the organization is delivering that magical intersection of customer value and business value, with examples of the key practices and mindsets to achieve that, especially deep customer understanding.— Cameron Moore, VP of Product at Dialogue (Formerly: OpenCare & Kijiji)
2. How would you improve a product you use every day?
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 lead to more natural product functional questions and start to unravel the key riddle: Is this a good personality fit?— Mike Leibovitz, Senior Research Director at Gartner (Formerly: Pivotree & Extreme Network)
3. 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.
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 they learned from, with little defensiveness.— Alex Weinstein, Chief Digital Officer at Hungryroot (Formerly: GrubHub & eBay)
4. What’s your biggest screw-up and what did you learn from it?
I look for the following attributes:
— Eric Carrasquilla, EVP & Division President at CSG (Formerly: Conga & [24]7)
5. What effect did COVID have on your Product Management lifecycle?
I’m looking for an understanding and awareness of mitigation planning.— Sunit Mohindroo, CPO, CityLitics
6. How do you scale yourself effectively through a team of PMs?
For management roles, I have always focused on a three-pronged assessment: Skill, Scale, and Speed. As a PM lead, they should be a good individual contributor, then be able to scale through a team by setting the vision, creating an ownership-based org, and effectively delegating responsibilities. Finally, they need to unblock the team through fast decision-making and facilitation of systems/processes for smooth cross-functional agility.— Manish Sharma, Investor (Formerly: Symphony & Facebook)
7. What is your approach to finding, growing, and retaining top-tier performers? Can you give me an example of where you did this well and not so well?
Being able to find, grow, and retain top-tier performers is one of the best signals of a great product leader. This question lets me dive into a candidate’s real-world experiences of doing this successfully and what they learned from doing this poorly.— Justin Dilley, Senior Director of Product Management at Axon (Formerly: Loopio & Amazon)
8. 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.
So much of being a good PM is prioritizing, and if you can’t do that regularly, it’s tough to lead.— Michael Cohen, CPO, Achievers (Formerly: LoyaltyOne)
9. Given diversity and inclusion are 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?
This is a really important attribute I look for and ask of any senior leader in technical roles, including product.— Seema Lakhani, CPO, Wattpad (Formerly: Torstar Digital)
10. Do you like people?
No further explanation needed.
— Marco Di Giacomo, EVP & CMO at Amagi Corporation (Formerly: Verizon & Evernote)
These questions are designed to reveal not just your skills but also your mindset, adaptability, and leadership qualities. Preparing thoughtful, introspective answers can help you make a strong impression in your next interview.
Looking to stand out even more? Check out our top 5 interview preparation tips to elevate your responses and land your dream PM role
Toronto Product Management Association (TPMA) is a community focused on development, growth and networking of Product professionals in the Greater Toronto Area.
