20 Product Manager Interview Questions from Product Leaders

Thanks to Lenny’s podcast, where the questions came from, and Eugene Segal for the inspiration for this post.

Here are tried and tested questions that some well known product leaders like to ask. If you’re prepping for interviews, make sure you have answers to these, and if you are hiring PMs then see if they work for you.

What did you ship most recently?

Laura Schaffer, VP Product Growth, Amplitude

I will ask about an initiative the candidate released, which was not cherry-picked by them. Everyone has a success story. I don’t want it. I want to learn about candidates’ frameworks and approaches, and less about the outcome.

Take me through your biggest product flop. What happened and what did you do about it?

Annie Pearl, CPO, Calendly

I want candidates to be brutally honest about how bad it was and why it failed. During the interview candidates try to tell you all the amazing things they did and their successes. And so, the rawer the answer regarding how bad it was and why, the better.

Tell me about a time you delivered something impactful

Lauryn Isford, Head of Product Growth, Notion

I’m looking for signals to help me understand how they define impact and what it means to them. A good answer for product people is an intrinsic motivation to impact the business.

How would you describe a database to a 3 year old?

Marily Nika, AI Product Lead, Meta

I love asking it because people think: “WTF did she just ask me?!” I believe it’s essential to be able to explain complex concepts in a simple manner using storytelling and explain technical topics to non-technical people.

Walk me through the story of you from college until now

Vijay Iyengar, Director of Product, Mixpanel

It’s an open ended question, and I want to learn where people spend most of their time talking and where they don’t. It’s also informative to see how they describe their journey to others.

Tell me about a product you love

Ravi Mehta, ex Meta, Tinder, Tripadvisor

I use the word “love” very deliberately and I want to see which products they gravitate to It helps me understand a lot about what the candidate values. Then I’ll ask a series of questions, like why they love it, why they think others love it, what they’d like to see in the future, a feature they’d like to build for that product, why they think it’s a good feature, and how they would measure the success of that feature. It’s a great way to understand a person’s product sense and get to know them better.

I ask behavioural questions, and then I ask the interviewee to imagine they are a coworker, and to describe the situation from their perspective.

John Cutler, Senior Product Director, Toast

This highlights self-awareness as people often answer the first part as the story’s hero. Challenging them to consider other persons perspective, shows how flexible they thinking can be about the situation.

What is something work-related that you’re trying to get better at?

Jules Walter, Product Leader, Youtube

I want to understand people’s self-awareness, growth mindset, honesty, and vulnerability. I find the most value in follow-up questions based on their answer.

At this stage in your career, what have you learned about yourself? How are you different from other people?

Ian McAllister, ex Uber, Airbnb, Amazon

These questions enable me to assess the interviewees self-awareness and ability to leverage their unique strengths for professional growth.

No specific question, but focusing on grit, endurance and drive

Sachin Monga, VP Product, Substack

I want to learn how diverse the candidate’s experiences might be for Substack. I look for people who can run through walls to accomplish big goals, and have grit, endurance and drive.

Fast forward three years, what is different about you then?

Ben Williams, ex Synk

I am looking for signals of humility and self awareness about areas of personal and professional growth.

Teach me something you don’t think I know

Adriel Frederick, ex Reddit, Meta, Lyft

This is an excellent test of empathy. This question helps me understand how well someone reads me, how much knowledge they have, and their ability to communicate and share knowledge.

What problems are you looking to solve and why did you come to this table?

Janna Bastow, Co-founder, MindTheProduct

Candidates must articulate their genuine motivation for joining, and show that they did their homework around problems that need to be solved and how they would resolve them.

What is a risk you regret not taking and why?

Jason Shah, ex Amazon

Through the “risks” question I aim to learn about candidates problem-solving and bets placing approaches. I want to identify candidates with a growth mindset who can reflect on their performance and voice self-criticism without unproductively being hard on themselves.

Teach me something new in one minute.

Ryan Salva, VP Product, Github

This is my icebreaker interview question, particularly for early to mid career product managers. I’ll pull out my phone and start the timer and then graded on three criteria: completeness, complexity and clarity. The most exciting thing someone taught me was about 18th century art and its connection to religious trends.

A group of scientists have invented a teleportation device. They’ve hired you to bring this to market. What do you do?

Shishir Mehrotra, Co-founder + CEO, Coda

All these different questions will come out, and at some point I’ll say, “Turns out the scientists hate talking to people and so they’ve decided that they will answer only two of your questions. And after that, they expect a plan. What two questions do you ask?”

And good people very quickly find what are the one or two eigenquestions on this topic. There’s no right answer, but one of my favorite ones is: “Is it safe enough for humans or not?”

What are your top 10 accomplishments?

Barbra Gago, ex Miro

People usually dislike this question because it’s challenging. I want to understand the level of quantitive versus qualitative accomplishments. Answers range from “I ran 100 miles” to “I have a great family”. It’s an insightful way to get to know someone and what they value.

Tell me about a time you crafted and implemented a product strategy.

Eugene Segal, Group PM, Miro

I want to step up from an initiative level and understand the candidates thinking about product strategy and how the strategy they crafted is connected to the company’s vision, mission, objectives, and growth levers. I also like to dive into execution by understanding the big bets, and those bets’ prioritization and metrics, and finally diving into the specific initiatives and those initiatives’ impact.

To do you attribute success? And you can’t say luck.

Eeke de Milliano, ex Stripe

I’m looking for self-awareness and curiosity, and I want to see if candidates have reflected on why they are where they are today.]

What have you done on your product since you applied to Y Combinator? What are specific things that you’ve accomplished since you applied?

Gustaf Alströmer, Parter, Y Combinator

This question allows me to see the progress and accomplishments the founders have made between applying and the interview. It’s important for me to see that they’ve been working on their product, and not just preparing for the interview.

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