Thoughts on Startups

Best Product Management Interview Questions I’ve Been Asked

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If I’m counting correctly, I’ve interviewed in the ball park of 30-35 different companies for different roles, often times doing multiple rounds of interviews. Of these, around 26 of them have been for product manager roles in varying capacities, from typical product manager roles to director or principle product positions. I’ve been asked some god awful questions (such as stupid challenge/trick questions) to exceptionally great and hard questions. I’ve done extremely well in some and felt great about the outcome, others I’ve felt like shit and totally bombed.

Over the years, these are the questions that have stood out to me the most as great questions to ask at each of the different interview stages. Note that this isn’t meant to be a full comprehensive list, just the ones I personally felt to be the right questions to be asking.

Phone Screening/1st Round

Why our company? What caught your eye? I like this questions specifically because it shows why a candidate is interviewing there in the first place. Are they here for a paycheck or do they actually have some passion about the problem space?

What do you see as a challenge in this industry? Even if the candidate doesn’t have a great grasp on the industry just yet, what you’re looking for here is if they have opinions about what may be hard. For example, a candidate might say that data collection for a certain vertical is hard and follow up with why they believe that. This shows that they did some research, can hold an opinion, and are genuinely curious about the problem space.


Describe to me a product you love and how you would improve it. For me, the best results of this have been when the candidate whiteboards this out. I find this question interesting because you get to see how they generate solutions on the fly to things they see problematic.

Let’s say you have a Kindle. You buy a book and then read it. Draw what that process looks like. There are no right answers to this question but very wrong ones. This is best captured on a whiteboard. As an interviewer, the best results is to sit back for 5-7 minutes and just let the candidate go at it without any help from you. Be silent. This questions helps show how a candidate views problems, maps them out, and works through different scenarios.

For example, to answer part of the question the candidate would probably think about things such as handling authentication, book delivery, book recommendations, email confirmation, etc. The candidate then may question how exactly do you deliver that book. Where does the book come from? When we deliver it to the Kindle, what other information are we passing down? Where does that information come from? It’s an exercise that shows how someone goes about problem solving, what their logic process is, and where they are strong/weak at.

What do you do in your spare time? What sort of personal projects are you working on? It’s good to know whether or not a candidate has outside interests and if they have a drive to continually learn.

What books are you reading right now? What do you enjoy reading about? More of a personality question but, much like the previous question, this is a good way to understand who the candidate really is. What interests them? Do they like to learn? What areas of personal growth are they focusing on?

Second/Final Rounds

We have this problem in our company. How would you solve it? One of my favorite things to do is whiteboard with people. I enjoy problem solving and find this question to be great for both parties to get a feel for how each other work.

As a candidate, I want to see what you’re like when I challenge your opinions, suggest new ideas, and how we would work together to solve problems. As an interview, I receive the same benefits but also get to see how you problem solve on your feet.

What do you want to be when you grow up? Where do you think you want to end up? Lots of companies look for ambitious product managers who want to learn, grow, and progress their career.

Take a walk with the candidate. This isn’t really a question but more of a personality filter. Get them out of the office, have them relax a little bit, and see what they’re all about. If you’re going to be spending a lot of time with someone, make sure it’s someone who you can be comfortable with.

There isn’t one way to interview candidates and every company or person has their own flavor for figuring out whether or not they fit. Some require presenting a roadmap, others weigh personal history and background.

What questions were you asked that you felt to be the “right ones?”


How to Handle Failure

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I’m fairly qualified to talk about this subject. I’ve failed at many things. Lots of things. In many different subjects. I’ve failed at businesses (4), failed at client projects (3), failed at school tests (5), failed at relationships (10+), failed at jobs (2), failed at delivering features (1), failed at winning (100s+),  failed at interviews (2), failed at being a friend (5), and have failed on countless other areas. Both big and small.

I don’t like losing and I especially don’t like failing. I find it incredibly painful, take it very personally, and very seriously. I’ve been a competitor my whole life and failing is something that I’ve never gotten used to, and never want to get used to.

Failure sucks but it is inevitable and crucial for learning. While there are different ways of failing or handling “graceful degradation”, I’ll only explain how I know how to handle failure.

Failure Means That it’s Already Here.

I used to beat myself significantly to the point where I’d be depressed. I hated it. However, I’ve changed my thought process to realizing that if I’ve hit the point of failing, that I cannot change the failure in that moment. The moment is already here and it’s going to suck. I’ve changed my thought process to accepting that the failure is here versus a continuous blame, sadness, and depression. Instead of running from it, I face it. By doing this, it doesn’t prolong the failure and gets you back into a state of problem solving faster. You start saying “I’ve failed. What’s next? Where can I go from here?” instead of drowning in anxiety and clouded thoughts.

Handling Failure Starts with Saying “It’s Ok”

I always felt like everything I touched or did had to be successful. I still feel that way. When things don’t go the way I expect it I now shift my thoughts towards acceptance. If a failure has happened and I’ve accepted that I can’t change the past, then I accept that it’s ok that the failure happened. Accepting it helps bring in the realization that you cannot change the past.

Focus on What’s Next

Being positive helps in any situation – especially in failures. There’s no point in dwelling in the past, especially if it’s in a business setting. If speed is of the essence, then you need to refocus and course correct. I start thinking about where the options are, what are the different possibilities with different outcomes, which outcome do I think is most favorable, and how can we get to a better resolution faster. I find it helps incredibly to constantly think about what’s next in a positive format because the options will present themselves much more clearly than if I hold in anxiety and think about the now.


Once the worst has past, I take some personal time away from the situation (personal or professional) to think about what led up to the problem. The best way to approach this is by playing the blame game but approaching the problems from a pragmatic approach. This includes yourself. I’ve found many times that I can trace back actions that I’ve made as major contributors to failures which helps inform me of future improvements.

This Too Shall Pass

Remember, we’re on a pale blue dot in the vast cosmic sea. Failures may feel painful while in the present but always feel less painful afterwards. All failures will pass as long as you let them pass. It’s critical that you don’t hold on to them as it will hurt you, cloud your thoughts, and make it challenging to find the next steps. In the scheme of life, the failure is small and insignificant.


7 Things I’ve Learned Recently

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Life is pretty interesting with the direction that it will take you, who it will introduce you to, and the lessons it will teach you in weird ways. I recently had some pretty impactful changes and figured it would be good to share my recent learnings.

You can never be to cognizant of your business health

In the past few months it has become apparent that when you run a company, no matter the size or growth you’re experiencing, you can never be too close to the core fundamental business metrics. It’s important to keep an eye on critical areas of revenue, profits, growth, retention, and reduction of complexity. Having a core vision that you have conviction around is paramount for bringing people together as well as providing a lighthouse, dictating what metrics matter the most.

Be open to meeting with unique people

I’ve recently started saying “fuck it, let’s meet” more to random strangers who reach out. I’ve done the same as well by randomly reaching out to people in different industries to learn about their work, their successes, and their failures. I’m not sure what has recently triggered this but it has been incredibly enlightening.

For example, I went to a bioinformatics MeetUp recently and learned a lot about what challenges bioinformaticians face with their day to day work and what matters most to them. Turns out, having open data within the science community is really important. Who knew! Apart from that, I’ve met some individuals recently who have challenged my frame of thought and helped me develop a different framework for thinking about problems.

My take away lesson was to put yourself out there and talk to people you wouldn’t have otherwise – especially in different industries. I’ve found that understanding how they solved their own industry problems can translate into solving your own industry problems.

Be confident about what you’re worth

Pretty simple learning here: don’t devalue what you believe you can offer to others. They may not see the same type of value which can either tell you a lot about the person or provide a conduit within a conversation to explain how valuable you are. This isn’t to say that you should be cocky, but I’m finding that it’s important to have confidence in yourself, believe that you’re worth what you think you’re worth, be persistent and consistent in that confidence, and implore that on others who may not see the same way.

Life is pretty short

I know everyone says this but seriously, god damn does it feel short. I know this is a typical thing for someone to say and dumb to reiterate at my young age but… it really feels short. I think about where I was two years ago and it is shocking how fast things can change. However, I was reminded that life is also long, depending on your perspective, goals, and ambitions at that current time. What’s short now may seem long in the future. But for me, right now, I can’t seem to get enough time on my side.

Graphs are probably the future of computer to computer interaction

I had a great conversation recently with a colleague who is exploring different types of graphs as a method of computer to computer communication. In essence, individual components have their own operating rules and jurisdictions that they behave by. However, when interacting with other components, they have contracts that can be extended in order to have a meaningful “conversation”. This is critically important when working in increasingly complex situations like supply chain management, ERP, and other enterprise business functions.

Furthermore, with the internet of things coming into force, this complex graph of “things” will need to have a concrete way of sharing data with each other. You don’t want to have a situation where a street light isn’t talking to a car giving it instructions only to find out that the car isn’t talking the same language. That will end up bad.

The core principle is that components can have many data ingestion points to make decisions but have binary outputs that interact with other components that make binary decisions based on lots of data points, and so on. The method for this is called Intelligent Agents and is a subset of development methodologies underneath machine learning. I’ll probably write an expansion on this topic soon.

Every bad or tough situation has massive opportunities

Being put randomly into these situations sucks because it’s pushing you into the unknown. I hate the unknown. I’m always trying to be 100 steps ahead and super calculated. But alas, shit happens and what matters is being able to react in a flexible manner. Instead of victimizing yourself, I’ve found it better to look at the situation as “Now that I’m here, what are the good things about this situation? What unique opportunities do I have that I didn’t have before?”. Always look for the positive, even when shit really, really sucks. I’ve found that things typically course correct themselves and opportunities start opening up usually in less than a week. This all comes back to networking and being confident. Trust yourself in finding a way out of the shitty situation, even if the way out is completely unclear.

Saying no to features is hard. Finding features that are game changing is harder.

Both are difficult tasks of a product manager. You have lots of competing priorities and objectives and your job is to act as a shit umbrella and a filter. You have to have extremely firm but loosely held opinions about the world. It’s hard to say no to features that don’t align with your long term vision. If you cave in to those feature requests, they’re going to come back and bite you in the ass.

Even more hard is finding the features that are really game changing for customers. This is what makes a good product manager valuable. Often times the answer isn’t clear and the customer doesn’t know exactly what they want. It’s a 50/50 balance of solving their pain points now but also showing them the future. I advocate solving customer problems but really think that doing this constantly doesn’t progress you as fast as it could. If I constantly solve for a 10% gain, then I’m competing with the market (you need to do this because it’s the bread and butter). However, if I’m able to give a 10x solution to a problem, I’ve leapfrogged the market significantly. Often times, solving for 10x is incredibly unclear.

These are probably pretty obvious, hippie-millennial talking point and learnings but they’ve recently been really reinforced in the past couple months for me. Things are often not as bad as they seem initially.