The Worst Product Manager Interview Question I Was Asked

I share this story as a form of catharsis and in the hopes that others will find solace in my lessons. Someday, you could be the person being asked a really shitty interview question, and I want you to know: it’s OK. You too could hear something, be entirely flummoxed, and then realize, nope — I am about to lose out on a job because the person interviewing me just asked me a question that makes no flipping sense. It’s not your fault. It’s the company’s fault for being terrible at building a culture that values good hiring practices. Blame them, not yourself.

My “worst question ever” came this past May, when I landed an interview for a Product Manager position at one of Silicon Valley’s current darlings — a hyper-growth unicorn that was quickly building out its product manager practice. I would have been hired as one of the more experienced members of the team and by all accounts, I had seriously impressed everyone. I was feeling comfortable, relaxed, and confident by the time the final interview rolled around.

My first conversation went really well. We did a lot of whiteboarding and product ideation, which is something squarely in my wheelhouse. All the product strategy questions and discussions were fun and conversational.

Then comes interview number 2. Now, I usually don’t mind interviews. One of my specialties is user research, so I’m pretty comfortable at establishing rapport with people even in awkward situations. But, it was clear from the get go that this guy viewed our interview much less like a conversation and more like a battle. He was in charge of testing me, and I was there to submit to his challenges. Hint: it’s difficult to establish rapport with a candidate when you treat them like an adversary, however “chummily” you’re doing so.

Blerg, so there was bravado involved, which was going to make this conversation much less fun and much more annoying. But, I could deal with bravado by answering all his questions intelligently and with as much logical ownage as possible. Challenge accepted.

After the customary bragging about our backgrounds, he started with his first scenario, which is apparently a hackathon. OK, I could dig that.

“So, you’re on a team of 4 or so people. You’re the product person, and you’ve decided you want to build a product to beat Uber.”

Me: “Cool. Sounds like a challenge!”

“So, what tech stack would you use to beat Uber?”


“Can you repeat the question?”

“What tech stack would you use to beat Uber?”


Tech stack…what the fuck does that have to do with beating Uber? What am I missing?

“Can you give me a little time to think about it?”


I quickly go through the possibilities in my head. Is this some sort of trick question? Is he testing my ability to say no? What does a tech stack have to do with competing with one of the most successful and well-funded companies on the planet? More importantly: why am I being asked this question in a product manager interview?

While a product manager absolutely should have enough technical chops to communicate fluently with his or her engineering collaborators, his or her job is not choose the technology driving these products. A product manager’s job is to understand the strategic and tactical landscape, so that the right product gets made to achieve your goals. You will likely deal with technical requirements at some point (e.g., “System needs to have an uptime of 99%”), but you should be agnostic about how they are implemented. A product manager should care about the ends, not the means.

Which is why the question, “What tech stack would you use to beat Uber?” made no sense to me. I wouldn’t even think about a tech stack when hacking together a product — I would think about markets and user experience and people’s goals…because that’s how you build things that people want to actually use.

So, I took issue with the premise, because I like shooting myself in the foot. My answer went something along the lines of:

“Well, I don’t think Uber was successful because of their tech stack. It was their user experience, not their technology that made them successful. Also, I think they were successful because of their launch strategy in a niche market in San Francisco, which had a very broken taxi system. ”

Him: “But it was their app that drove their success. That’s technology.”

Me: “Actually, I’d argue that it’s because they integrated the ability to call a car and pay seamlessly, which was a significant improvement compared to the status quo of needing cash or swiping a card. You could do that a bunch of different ways and still have it be successful. You could concierge it, actually. The tech stack is pretty irrelevant. That’s user experience.”

Him: “So how would you beat them?”

Me: “Well, they don’t have the best PR. I refuse to use them because I think they are a terrible company and know a bunch of people who share that sentiment. But, I think their biggest weakness is likely in their legal issues with contractors (Side note: So fucking vindicated). Internationally, this is especially going to be a huge issue. So maybe I’d go international and do something grassroots — work with governments, rather than against them. Especially in places that need to beef up their public transportation infrastructure. Also, WhatsApp had a lot of success using data instead of SMS because of the cost of text plans internationally. I’d probably look into how user incentives might take advantage of SMS credits or go into markets where smartphones aren’t as prevelant since people tend to forget about them. Maybe you could call a car with SMS or somesuch.”

Him: “Sounds like you’re really onto something there. So for this idea, what tech would you use?”

Me: (Internally) LOUDLY SCREAMS.

To be fair, I believe I actually answered the question with something about how international markets are primarily Android, so I’d probably go Android first, so there’d obviously be Java and beyond that I didn’t care, but would work with the team to figure out what made the most sense depending on the requirements.

Suffice it to say, the rest of the interview wasn’t ideal — I took issue with the premise of a number of the scenarios presented to me because I honestly wanted to do the right thing, rather than just say what I think he wanted to hear. But, I came out feeling fantastic about my answers — I felt they were all representative of great product manager thinking.

I’m sure there are a few of you reading this who are going to try to give my interviewer the benefit of the doubt. I’ve discussed this interview a number of times now and the most common defense is that he was likely trying to test my “technical abilities.” If that was the case, there are SO many better ways he could have done that, not the least of which would have been asking me about them. I have a Computer Science degree and would have been more than happy to chat about any number of topics that could have given him a glimpse into how I collaborate with engineers or think about technology. Instead, he asked about my abilities in a bizarre way that left lots of room for misinterpretation. You’re trying to get a clear understanding of how another person thinks: make it easy for them to talk to you!

I didn’t get an offer from this company, and I actually think I dodged a huge, cannonball-sized bullet. I have inside information that I lost the job pretty much entirely based on the interview described above, despite stellar recommendations from everyone else.

Sadly, this isn’t the only serious fuckup the aforementioned unnamed startup made during my interview process nor are they the only company to make interviewing a huge headache. I could do a series of blog posts about all the things that companies did to make my life as a candidate miserable, but I’m pretty sure I’d fall into a deep depression before I finished it. As someone with a background in user experience I can tell you this: I’m not sure there was a single company who had hiring practices that allowed them to accurately determine if I was a good fit for their company.

Basic Truths I Uncovered While Being a Product Manager Candidate

  1. People in the startup world have no fucking clue how to interview or hire. I hypothesize this is because people don’t make it a priority to actually train or learn basic interviewing skills. And yes, learning how to evaluate candidates’ abilities is just as difficult and as important as any engineering or UX skill you can name. This means critiquing each others’ interviewing skills and learning as a team about how to improve the hiring process. Ask yourself this — when is the last time when you were an interviewer and you were asked about what questions you asked the candidate, your own biases, and how you could have improved? If you answered anything other than “never”, give yourself a prize because I suspect you are an actual shiny silver unicorn.
  2. We still haven’t converged on a definition for Product Manager. This means some product managers are actually project managers or program managers or scrum masters or some bizarre amalgamation of 10 different things. You can have MBA-type product managers who are super finance-focused. There are others who are very much focused on user research and building the right features. But, since no one can agree, you have no idea which of these a hiring manager is looking for before you go into an interview. Most often, even they don’t know what they’re looking for and don’t know how to find it. This is really annoying as a candidate, since 75% of the time you’re not the person they’re looking for, but they don’t know it yet.
  3. Culture fit questions are very dangerous. You don’t want people who just think and act like your current team. Being a Product Manager requires challenging the status quo, which means you should probably be trying to hire people who actively push your boundaries and do things differently. The Product Manager role is often thought of as “nice to have”, but not critical, so the person hired often is not someone who is outside of the box in any way. Stop having “a box”. You think it’s too early to hire a product manager who specializes in user research? False. It’s never too early for user research. What about actively looking for a minority candidate? And I don’t mean just saying you’re excited about diversity. I mean actively combing your network, going to events, and finding that awesome black woman to lead your product manager team instead of using that easy referral for a white dude from Facebook.

Learn from my experiences. Hiring a product manager isn’t easy, but we can all get a lot better, very easily. And please, please, please: don’t ever ask what tech stack you would use to beat Uber. There’s just no excuse for that.