Questions I like to ask my interviewer

There’s a lot of advice on the internet for job candidates on how to answer job interview questions, but not much on how to ask good questions, the importance of which scales with seniority.

2 qualities of good questions

1. They’re open-ended

When I worked as a journalist, I learned one important thing about interviewing folks: the longer they talked, the more revealing their answers were. Open-ended questions take more effort & time to answer, and will give you more signal.

2. They require concrete answers

If a manager gives you a great explanation for how their PDLC is designed to work in theory, you have to follow up with “walk me through how your most recent project went from idea to deployed code”. Don’t be afraid to ask “why” in response to their answer. I’ve even asked folks to screenshare or demo during interviews =)

Questions I like to ask

Can you walk me through the PDLC of your most recent project?

The quality of the answer generally comes down to how early engineers are involved. Follow-ups include “who had the idea for this project?” “what other ideas were considered?” Bad answers can tell me it’s a feature factory with disengaged engineers and clueless product managers.

Tell me about your favorite user?

If the interviewer doesn’t know a customer by name, run.

Who is the best engineer you’ve worked with here and what made them great?

This is a great indicator for A) how collaborative the environment is B) the quality of people you’d be working with. “They ship a lot of code” is a bad answer.

What’s your favorite feature you’ve shipped?

Everyone should have a favorite feature. Why it’s their favorite feature will tell you a lot. I’ve failed a lot of interviewers (and candidates, TBH) because answers to this question sucked, e.g. “I fixed our internal admin tool” or “I made an internal scoreboard for who did the most refactors”

How did you measure success?

This is typically a follow-up question. Good answers range from “The customer sent us a nice email” to “We Scrooge-McDucked into the money this feature made”

What’s the biggest failure your organization has had?

Every organization has failures. Mostly failures, in fact. If an interviewer struggles to answer this question, it may mean they don’t openly acknowledge failure or don’t know how to measure success, both of which are red flags.

What are the three most recent things you’ve said “no” to?

This is a really important question for managers, PMs, and staff ICs. Time is the most precious resource, and you can judge how folks spend it by how often they say no.