Interview questions for early startup hires
Assess candidates quickly and with high accuracy
I've always seen interviews as a sort of optimization problem. You want to spend as little time as possible to assess a candidate with as much accuracy possible. Accuracy matters more the better a candidate is, so you should also spend more time to pinpoint the abilities of a great candidate vs a mediocre one.
Most interview questions are more indicative of interview prep than skill, they don’t let outstanding candidates shine, and they take too long to answer. So what questions should you ask if you care about fast and accurate assessment?
What's a complex project you've worked on that you're particularly proud of?
This is my favorite question to assess if someone is exceptional at their craft. After the initial answer, I like to go deep and ask lots of follow-up questions. The deeper I can go, the stronger the candidate.
Don't be afraid to really dig deep and ask Why an uncomfortable number of times. Exceptional candidates will understand the chosen topic so well that they’ll enjoy navigating the details with you. Also, try to understand the candidate's contribution vs. that of the team. If everything is framed as "we did x, y, z", and the candidate won't speak about their own substantive contributions that's a negative sign.
What's your perspective on work life balance?
I’m looking for people that have an optimistic relationship to their craft. People with genuine passion for a field have the most important advantage of all because all the time they spend honing their skills outside of work compounds in ways that it doesn’t for someone that has an adversarial relationship to work.
By asking the question in a neutral way you can usually tell if someone thinks about work and life as a strict tradeoff or if work and life are more complementary and mutually reinforcing. Also, passion is the most important pre-requisite for hard work, and this question tends to elicit it in a way that asking a question like “What’s the hardest you’ve ever worked?” does not.
What kind of culture do you want to be part of? Besides the things everyone wants like smart and kind coworkers, what uniquely matters to you?
You have to reject some super talented people if they are bad for your culture. I’m often asked about culture at the end of interviews and I’ve noticed it’s useful to try and ask the candidate first so that you get a less biased answer.
There are many flavors of great culture. Some prioritize speed at all costs. Others prioritize craft and nailing the details. Some are intense and top-down. Others are more creative and collaborative. There is no best culture. But there are cultural attributes that bring out the best and unlock the most potential in a person. If there is a cultural trait at your startup that makes you unique and that you want to cultivate, you should ask about it directly.
If you were to join us, how would you want the first days and weeks to go?
People that get things done tend to think about solutions in sooner and shorter time intervals. Today instead of tomorrow. Days instead of weeks. Weeks instead of months.
You can get a sense for someone’s views about speed by asking them how they think about onboarding. Do they want to jump on a sales call or put up a PR on the first day? Great sign. Do they expect to spend weeks in formal training? Not the right fit for a startup where learning happens through osmosis, failure, and getting your hands dirty.
The worst hire I’ve ever made wasn’t a good fit because all initiatives, no matters how mission-critical, would never be kicked off before next quarter. The person believed that as a startup we were constrained by the same bureaucratic process that stifles large companies. But the most amazing thing about startups is that you can have a brilliant idea in the morning and start executing it immediately.
Who are some people that you admire or look up to in your field?
Great people are intensely curious about the field they operate it and almost all genuinely curious people make an effort to find people they look up to — heroes, experts, mentors, etc. While easy to lie about curiosity when asked directly, I like this question because it surfaces curiosity in a way that lets really great candidates stand out.
What questions do you have for me?
Always leave sufficient time for candidates to ask questions. So many things you do at a startup come down to making sure you are asking the right questions, so being able to see if a candidate can figure out what the most important questions are for them to assess the role/startup will tell you a lot about how they tick.
This is also the part of the interview where a candidate can best showcase their curiosity, creativity, and generativeness. If an interview was okay until now but then they ask about a brilliant tactic I hadn’t considered, that’s the best way to win me back over.