Leadership Questions
This is a collection of prompts typically asked of product leaders. You will see 9 categories of questions.
Behavioral
(~10% of questions)
Tell me about yourself.
Teach me something you don’t think I know
What are your superpowers? And their shadows?
Fast forward three years, what is different about you then?
When I go ask people you’ve worked with about you, what will I hear?
During your career, what has been your greatest achievement and why?
Among the people you’ve worked with, who do you admire most and why?
At this stage in your career, what have you learned about yourself? How are you different from other people?
For the last few companies you've been at, take me through: (i) When you left, why did you leave? (ii) When you joined the next one, why did you choose it?
Who is the person whom you’ve had the most difficulty working with? Why was it difficult, and how did you work through it? What would they say about you today?
Team Management
(~13% of questions)
What’s your managerial style?
When’s the last time you fired someone?
Who’s the best hire you’ve ever made and why?
How do you help your team to learn and develop?
How do you earn trust and respect from your team?
How do you say no to the CEO? When’s the last time you did?
How do you approach diversity and inclusion within your team?
How have you dealt with negative or static mindsets within your teams?
Give an example of a time when you had to deliver bad news to your team.
What’s the most negative feedback you’ve received from someone on your team?
Tell me about a time when you coached or mentored someone in your team. What was the effect on their career?
What's one part of your previous company’s culture that you hope to bring to your next one? What one part do you hope to not find?
Tell me about a time when your team didn’t gel. What was the issue, and how did you deal with it? Has this happened on other teams you’ve been on?
Who is the best person you’ve ever hired, and why?
Product Basics
(~10% of questions)
Tell me about a time when you identified a hidden or unaddressed user need. How did you discover it and how did it influence your product strategy?
Can you discuss a product decision you made that went against prevailing trends or industry wisdom? What was the rationale and the result?
What’s the most important or impactful product you shipped? What made it so important or impactful?
Take me through your biggest product flop. What happened and what did you do about it?
How do you think PMs should interact with engineers and designers? What’s the role of a PM?
How do you balance insights that come from data against those that come from intuition?
Describe a time when you had to pivot your product strategy based on market changes.
What’s your favorite product and why? How would you improve it?
What launch in the last year are you most proud of and why?
Give me an example of a time your product failed and why.
Product-Specific
(~10% of questions)
Given our current product, if you had unlimited resources but also a tight deadline to achieve a significant impact, what bold steps would you take?
Analyze a major failure or setback our product had in the past. With hindsight, how would you have approached it differently?
Based on what you know now, what would be your strategy for our product?
How much have you used our product? What research have you done on it?
How would you assess the current market positioning of our product?
What user personas do you think we are not fully targeting enough?
What key features do you think are missing from our product?
How would you force-rank our customer segments?
What should we do with AI in our product?
How big should our product team be?
Product Leadership
(~18% of questions)
Discuss a time when you had to make a tough prioritization call that impacted your product roadmap significantly. What was at stake and how did you decide?
Share an experience where you had to champion a product vision that was not immediately embraced by your team or stakeholders. How did you gain buy-in?
Share an experience where you turned around a disengaged or underperforming product team. What specific actions did you take and what was the result?
Describe a scenario where you had to balance strong leadership with team empowerment, especially in a high-stakes product decision.
Based on your experience, where do you think product management is optimally situated in the organization? Why?
How do you stay informed and connected on market trends, new platforms, the evolution of product teams, etc.?
How do you handle budgeting and resource allocation for product development?
What’s the biggest one-way-door product decision you’ve ever had to make?
Walk me through the most complex design issue you faced in your last job.
What metric goals did you have in your last role, and did you meet them?
How do you build and maintain a high-performance product team?
What types of product rituals do you establish on your teams?
Can you teach someone to be a good product manager? How?
How do you teach someone to say “no” effectively?
Describe an experience handling a product crisis.
What’s your point of view on Product Ops?
How do you structure your product teams?
How do you decide what to work on?
Non-Product Collaboration & Impact
(~7% of questions)
How have you leveraged insights from customer support or user feedback loops to redefine product strategy? Provide a specific example.
How do you enhance the relationship between go-to-market, design, and engineering?
What’s been the worst relationship with engineering you’ve had in your career?
What's your approach to handling conflicts between product and sales teams?
Describe a time when you had to negotiate resources from other departments.
How have you worked with Sales/ Marketing/ Customer Support in the past?
How did you work with the Senior Leadership Team in your last role?
Product Design
(~8% of questions)
What innovative design elements would you add to a ride-sharing app?
How would you approach designing an educational app for children?
How would you improve product X (eg, Google Maps)?
Design product X for Y (eg, fitness app for kids)
What is a product you think is poorly designed?
Why did product X fail? (eg, Google Domains)
Redesign the city public park experience.
What makes a product well-designed?
Product Strategy
(~14% of questions)
Should X buy Y?
Why did Microsoft buy Activision?
Should X partner with Y?
Why did Netflix partner with the WWE?
Should X go into Z market?
Should Amazon compete with ChatGPT?
What should X build in the next 5 years?
You’re the CEO of X. What do you build next?
You’re the CEO of our biggest competitor. What do you do?
How would you assess and act upon potential international expansion for a product?
Describe a strategic pivot you had to execute. What drove this change, and how did it align with the overall business strategy?
Can you talk about a time when you had to make a long-term strategic sacrifice for a short-term gain, or vice versa? What was the situation and outcome?
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?
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?
Craft & Execution
(~8% of questions)
Share a time when you had to rapidly iterate on a product feature due to initial poor performance. How did you manage the process and measure success?
Discuss a complex technical challenge you faced during product execution. How did you navigate it, and what was the impact on the final product?
Pick a project you’re proud of that took 3-9 months. Walk me through it from beginning to end. I’ll ask questions along the way.
How would you address a significant drop in user engagement for a key feature?
Describe your process for prioritizing bug fixes and feature requests.
How would you measure success for Facebook Events?
What’s the worst tech debt you’ve had to deal with?
How do you decide when to build vs buy?
Resources
1. ProductHQ
2. aakashg.com
4. Reddit
