Stuff I’ve Messed Up While Interviewing

One of the things on my mind recently has been interviewing. We’re hiring for Product at Kickstarter, and I want to make sure I give people the best chance to succeed. (Interested? Please reach out on Twitter or via email!) I’ve also been talking with people who are trying to get their first job in Product. That culminated when I taught “How to Interview for PM” for Startup Institute last Monday.

As I’ve talked with people, I’ve found myself sharing a lot more “bad” interview moments than “good” ones.

It’s important to realize that one bad interview doesn’t mean you’ll never get a job. It might just mean you aren’t a good fit for that company, or that you didn’t prepare well enough.

I’ve had some terrible interview moments. These are the most embarrassing ones. I’m going to share a few specific interview questions for the sake of the stories, but that isn’t the point. My goal isn’t to “out” the questions that any company uses. You shouldn’t just try to memorize specific questions. I’m using these examples to show how to avoid making the same mistakes I did.

I also put a summary checklist of how to avoid these pitfalls at the bottom.

Fall 2005, Princeton – “Do you have any questions?”

I think this was the first interview I ever had. I’d jumped through all the paperwork hurdles and had an interview with a Princeton alum. No one had ever talked to me about proper interview technique.

We had an awkward conversation about Eating Clubs (I am a dork, didn’t care). We talked some about gender differences (Again, cared about robots, not gender). The interviewer and I were definitely different people.

That could have been fine.

The death knell was when we got to the end and she said “do you have any questions for me?” and I said “no.”

Nothing signals a lack of interest/research preparation more than not having any questions.

This is going to come up at the end of every single interview. Most interviewers even say “and I’ll leave five minutes at the end for questions” before you start. The questions you ask will be the interviewer’s last impression of you.

Have a list of well prepared questions before you go into interview. You should care about the answers. I’d recommend at least two per interviewer. If you don’t have any questions, the company might not be the right fit for you.

Some ideas to get you started:

  • Things about the interviewer’s role in the company (how long have they been there, best part, worst part, how it’s changed over time).
  • Things about products (what they’re most proud of shipping, which project was the most challenging & why).
  • Things about the industry.
  • Things about the team (what are you looking for next while you build your team? What skills are lacking?)
  • Things about the company as a whole (what are the next challenges)

Spring 2008, Microsoft – “Give me 10 ways to improve an elevator.”

People have been talking about this question for a long time (here’s the Quora discussion).

I don’t want to talk about the nature of “design” questions, though. There are lots of better resources to learn about that. Plus, my struggle wasn’t there. I’d already gone through all the typical pieces of the question that are covered in the thread.

The PM interviewing me was pushing me for more practical implementation details. At the time, I wasn’t great at practical things, and he could tell. He also thought I might not have follow through.

He was right. I got tired of the question and started saying things like “fine. let’s add luggage racks. and drinking fountains.” rather than thinking critically.

I screwed up by not being resilient.

The interviewer called me on it, and (verbatim) said “are you fucking with me?” I still haven’t met anyone else who got told to stop fucking around in an interview.

It seems stupid that I need to say this, but I messed it up. You should NEVER give up on a question mid-interview. Some questions are designed to test your endurance. Just keep working through them.

Fall 2009, Google – “Give me an example of real world iteration & recursion.”

This is the roughest interview I’ve ever had. I didn’t sleep the night before, but figured it wouldn’t matter much because it was only a half an hour phone screen. Usually those are softballs. This one wasn’t.

First, we talked about a Google product. I wanted to talk about Gmail (I used it daily) but the interviewer didn’t want to. Instead, we opted to talk about Google Docs. Unfortunately, the interviewer had been the Google Docs PM, and I’d only used it at a surface level. Every suggestion I made turned out to already be in the Product. Whoops.

If you’re going to talk about a Product, try to make sure you know it better than the interviewer does. For smaller companies, you should know the Product inside out. For bigger ones, try to know a few of their common & less common offerings inside out. Give yourself options for what to talk about.

Like I said, this was my roughest interview ever. After the Google Docs fiasco, we got to the single worst answer I’ve ever given.

The question was “Give me an example iteration & recursion in the real world.”

I know what iteration and recursion are in code. I had no idea how to translate that, on the spot, into real life examples. For what it’s worth, while writing, I found this cool academic article on it.

We stumbled around for awhile before I told the interviewer I just didn’t know. She tried to help, but it was beyond repair. It was awkward.

I’m not sure I ever would have gotten that particular question. It was my fault for not being more prepared. Google is known for having particularly technical PMs. I was expecting to coast on having an Electrical & Computer Engineering degree. Unfortunately, ECE definitely isn’t CS. I should have spent more time preparing for those types of technical questions.

Years later, I interviewed with a company that was known to be more business/revenue focused. The interviewer asked how I’d calculate Lifetime Value for a customer. I’d never had to do it before, and stumbled around with trying to figure it out. Similarly, I should have been prepared.

Figure out what the company you’re interviewing cares about. Know what disciplines the PM is expected to be familiar with it. Figure out how to answer interview questions for those disciplines, too.

(NB: When Google recruiters reach out to me now, they always say “we see you interviewed in 2009.” That forces me to reflect on the horribleness of the interview all over again. Some advice for Google recruiters: making me feel bad about myself doesn’t make me want to work for you.)

Winter 2011, – “How would you improve our product?”

In the Winter of 2011, I reached out to Kate Matsudaira for some unrelated career advice. We had a great talk over coffee, and she invited me to interview for a PM role at I was super excited about idea of working with Kate, and curious about being at a smaller company, so I jumped at the chance.

In my excitement, I neglected to notice that I hate comparison shopping. I’d much rather spend $20 more than spend an hour comparing. I also don’t put much stock in Product reviews. I’d rather just get one recommendation from a friend and go with that. I hate overanalyzing purchases. More often than not, I buy the first thing from the Amazon results. was a product that made it easier to do something that I never did.

I’d never prepared a lists of recommendations before an interview. Ideas for what I wanted to do with the Product always came naturally. Given I didn’t use products like Decide, I should have made a list. (I always make a list now, regardless of the company).

Because I didn’t do that, I struggled to come up with product recommendations during my first interview. It was uncomfortable.

That set me up on a bad path for the rest of the day. I was anxious, realized things weren’t going well, and had trouble focusing. When Kate asked me a neat interview question (which I’m not going to share!) I didn’t do as well as I would have liked – because I was so nervous from my previous experiences.

Do your preparation work for Product interviews – especially if you wouldn’t use the product.

Fall 2012, Kickstarter – “How do you feel about psychology?”

I wrote a bunch about interviewing for Kickstarter over here. The most stressful of the interviews was definitely when I talked to Perry, our CEO. I was more anxious than usual because I was getting to talk to Perry, and Perry is way cooler than I am.

Perry threw me curve ball questions. He wanted to talk about psychology. I kept trying to switch the topic to something I was comfortable with – design or organizational behavior. Perry kept us on the psychology conversation.

This didn’t end up going wrong, but it could have. If I’d had this interview a year earlier in my career, it would have messed up the entire rest of my day. I would have agonized over why he’d asked me that, if I had the right skills, etc. This luckily happened late enough in my interview process for me to just move on and hope it worked out.

Be ready to just have a conversation if that’s how the interview works out. Don’t overanalyze or let it throw you off.

Fall 2013, Spark Capital – “Have you made any friends?”

Late last year, a recruiter reached out to me about an Associate opportunity at Spark Capital. I’d never considered a career in VC, but it seemed intriguing. I went through the interview process, and I’m glad I did. I learned a lot about myself, and I’ll write more on that later.

The question that turned me into a babbling buffoon was “have you made any friends since moving to NYC?”

Product interviews are more removed – design this, how do you feel about X product. No one had ever asked me about myself in such an intrusive way during an interview. It didn’t help that I’m anxious about meeting people.

I should have realized that VC interviews might be different than Product interviews. I understood that the “content” would be different (I prepped to talk about different categories of products, business models, etc). I just didn’t get that there might be an entire extra dimension about “me” and not “my work.”

Don’t make assumptions about a new type of interview based off of what you’ve done before. Figure out what the standards are in your field.

So here’s my checklist for prepping for Product interviews:

  1. Know the expectations for the industry, if it isn’t what you’ve interviewed for before.
  2. Know the Product(s) inside out.
  3. Genuinely care about their product, and do extra prep if you don’t.
  4. Prepare Product recommendations.
  5. Know which way their PMs lean – do you need dev chops? Business? Design? Be ready to answer questions that are from the adjacent discipline.
  6. Stick with it. Never give up during the interview.
  7. Don’t let curve ball questions throw off later interviews.
  8. If something does throw you off, rebound.
  9. Have two different follow-up questions prepared for each interviewer.

ps – Update, March 2015. I’ve noticed a ton of you have found this today from Hackernews and I really like some of the advice/comments on the thread. Hello!