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Chris Arcand

Principal Engineer building Terraform at HashiCorp 👨‍💻 Formerly: Red Hat, NBC SportsEngine, RubyMN organizer. Once played the clarinet for a living, now making a living to play hockey. I make pointless connections to Minnesota as a Minnesotan does.

St. Paul, MN

Interview Your Interviewers

At this point in my career, I’ve taken a fair number of job interviews in the tech industry. I’ve interviewed at companies ranging from large enterprises to tiny consultancies and small, bootstrapped product teams to high-growth, VC-funded startups.

Interviewing is (regrettably) it’s own weird skillset, especially in software development. You’re not only expected to demonstrate that you’re technically proficient enough for the role (or can clearly learn the technical skills required) but also that your personality fits well with the culture of the team - all within a few hours, usually. To keep this unique skillset of selling yourself sharp, some people advocate taking at least one interview every year even if you have no intention of actually accepting a new role. While I acknowledge that taking interviews like this requires time and privilege that not everyone has, I think this is a good strategy overall and I’ve followed it for number of years now.

 I often get asked for advice on interviewing by colleagues, and there’s one thing in particular I always share first: Interview your interviewers. An interview is every bit as much an assessment of the interviewer as it is an evaluation of the interviewee.

Interviews are not a one-sided ordeal and you shouldn’t forget to evaluate your potential company as you sit on the candidate’s side of the desk or screen! Companies you want to work for will always offer to honestly answer any questions you have and make sure they reserve enough time in every interview to do so.

Interview your interviewers. An interview is every bit as much an assessment of the interviewer as it is an evaluation of the interviewee.

Treating an interview as a true evaluation of both parties has a ton of benefits:

  • You get more value out of the interview, getting a clearer picture of whether or not the role is a good fit.
    Job descriptions are more or less bullshit - or at least omit a lot of particulars - even at good companies. They are purposely generic and are never actually tailored to describe the actual details around a specific requisition (this is intentional - more on that later).

  • You shift the burden of answering questions and give yourself a break.
    Interviews are a lot of work, especially for anyone who tends to identify as more of an introvert. At many companies, candidates are evaluated by a panel of different people, each interview evaluating the candidate from a different angle. You might have interviews scheduled with plenty of time between them or you might get a few solid hours of interviews all in a row (hopefully not - but I’ve experienced this multiple times). Also consider that you might be interviewing at multiple companies at once!

    Regardless of the length of time, interviews can be socially taxing as you take interview after interview, trying to reintroduce yourself to yet another person for yet another hour. Asking good, open-ended questions actually shifts the burden over to the interviewer, allowing yourself to regain a little composure and mentally recover from constantly answering them.

  • You show more interest in the company and role to your interviewers.
    As someone who often sits on the interviewer side of the table as well, I’ve known people who saw a candidate not asking any questions at the end of an interview as a red flag. It supposedly signals that the candidate might not be all that interested in the company or role they are interviewing for. I don’t agree with this. Although it gives some small bit of insight in to a candidate (e.g. based on what they’re seeking clarification on, what do they seem to value?), blindly assuming the candidate isn’t excited about the role due to a lack of questions is a mistake. Nevertheless, it’s a common interviewer ‘tactic’ to be aware of.

  • You have a better chance of avoiding a bad situation. Just as you’re trying to sell yourself in a few hours time, you also only have a few hours one-on-one time with employees of a company to really deduce anything that you’d consider an absolute dealbreaker to accepting an offer from a company; things that don’t show up on paper in an offer letter but you might discover in some months’ time and realize the role or team really wasn’t a good fit for you. What sorts of things does the company value? Is there anything that makes you feel ethically uncomfortable that you might not have known about the company before? Do you have a clear picture of the expectations of the role and how your future team works together?

  • You might be creating the beginnings of a good work relationship with your future coworkers.
    By treating an interview as a two-way street, you’re really making it a conversation. Instead of a sequence of questions to answer and be done with, you might actually find yourself connecting with your future teammates. What better way for either side to evaluate if they’d be a good fit than by actually experiencing how you’d connect as colleagues to begin with?

So now that you know you should ask questions of your interviewers, what should you ask? I like to keep a personal checklist of potential questions to ask. If you don’t know where to start with your own list, Julia Evans has a solid list of questions to get you going in her post on the topic from 2013. Pick out ones that matter to you, add your own, and don’t be afraid to tweak them at any time.

In an actual interview I use a subset of questions depending on the particular concerns I might have for a specific company. The questions you ask can (and should!) vary between companies as each one is different. The company size, the role, and what stage the company is in (is it a privately owned startup? a publicly owned corporation?) will affect the priority of your set of questions.

Always ask a hiring manger why the team needs you in an interview. Job postings are almost universally bad at getting specific about the actual role in mind, even at good companies.

I’d specifically like to call out one question to make sure you ask your hiring manager. Always ask a hiring manger why the team needs you - or someone like you - in an interview. As I mentioned above, job postings are almost universally bad at getting specific about the actual role in mind, even at good companies. Part of that is because you haven’t signed an NDA yet, but another is that companies are usually pretty terrible at keeping job descriptions up to date and specific to a certain new role in mind. So don’t forget to have that question answered very specifically! An example: “What do you need the person in this role to do? If you hired me, what’s something specific that you hope I’ll bring to the company that will make you think ‘Oh wow I am so happy we hired him/her/them’ six months from now?”.

The Two Questions I Always Ask

There are two questions, however, that I always ask every single interviewer at the end of every interview - hiring manager, engineer, even the recruiter. If there are multiple interviewers in a single interview, I ask the questions in round, with each person answering the first and then reverse order for the second (as the person who answers the question last always has more time to think, so it’s more even this way).

They are:

  1. What do you absolutely love about <company name>? What makes you get to your desk every day and think ‘Oh yeah, this is exactly where I want to be, I’m really happy with where I’m at’?
  2. Conversely, what do you hate about <company name>? Put in a more positive light, what do you think <company name> isn’t so good at and could use some improvement?

I’ve found these questions to be - by far, in my experience - the most revealing things you can ask in an interview to gauge a company and what its employees think of it. You’ll find that these questions immediately set the interviewer at the same level, and the first few times you ask them you’ll be blown away by the bluntness and honesty that typically come with the answers.

  • Sometimes an answer to #2 will inform your question(s) for the next interview, so you can pry that subject open and see if you discover a major issue at the company that would make you feel uncomfortable. Sometimes the answer will be repeated by every single interviewer and immediately show a red flag that you’ll be happy to avoid by declining an offer (this has happened to me before!).
  • Other times the answer to #2 will be repeated and won’t be a red flag: every company has at least one problem, even good ones, and there’s always a tradeoff. So if it’s not a dealbreaker for you, you’re now just well informed as to what exactly you’re accepting (and will try to help improve) if you’re made an offer and choose to join the company.
  • The answers to #1 could cement your confidence that you’re making the right choice if you have the chance to accept an offer. What if you know exactly what’s most important to you and every one of your interviewers has the same idea? Answer: you might have just found your people.

Interview your interviewers and try to connect with people you’d hope to be able to connect with in the future anyway. It all sounds so obvious from afar, but sometimes hard to remember as you approach a set of interviews with that-one-company-you’ve-always-wanted-to-work-at. Ask lots of questions and don’t be afraid to really pry things open to be as confident as you can be that all of the effort you’re going through is worth it. Both the company - and you - are far better off for it.

Want to ask me these questions, and hear how confident I was joining my team at HashiCorp? (Spoiler: I was very confident) We’re hiring! Check out our open positions at

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