Questions to ask in an interview

The questions you ask in a job interview are important.

They reveal your level of experience, ability to form complete sentences, how much you were actually listening, passion level, and how seriously you take committing to an organization. While the goal of an interview is to get an offer, deciding what to do with that offer requires you to proactively seek information.

Feel free to ask questions even if you get to the end of the interview and you’ve managed to:

  • pronounce C# as “C-tic-tac-toe-board”
  • use airquotes every time you said “database”
  • completely bomb the technical interview (“Sir once again – you use the other end of the whiteboard marker to write”)
  • made a joke so lame everyone just looked down in shame (“Well, I think I would fit here because I-BM’d this morning! Get it?“)

If the interview is going well the questions you ask will arm you with critical information to do the right things in your first months on the job, and if the interview is going badly insightful questions can still be valuable – every interview is an inside scoop on how a particular company operates, what they value, and a chance to meet new people who are good at what they do – don’t miss it.

How to ask hard questions

The real questions you want to ask are at times too direct; they are the equivalent of asking a first date overly-intimate questions (“So what does you mom look like – does she have that eyes-too-close- together-Will-Ferrell thing going on too?”). While figuring out what you can get away with is an art and not a science, I’ll offer these random bits from my own experience:

  • You’ll regret the question that you don’t ask. It will haunt your dreams and bring shame to your family
  • It’s much easier to read people 1-on-1. If an interview is six people each talking to you for 15 minutes you can pick and choose who to ask based on what you read off of people – who seems to like telling stories from the “good old days”, who is an engineer and therefore stereotypically honest, who is going to give you the brochure answer? [Side note – some of the best information can be gathered from asking good questions of multiple people and comparing notes]
  • If you get invited to a lunch interview it’s a much better situation than in an office; the bar is lowered and people are more honest with their answers.

In the end the basic information you are trying to pull out of the interview process:

  1. Is the work-life balance what I’m looking for?
  2. Is the risk/reward situation what I’m looking for?
  3. Will I fit in, learn, and thrive?
  4. What are they trying to do?
  5. What happens when things go wrong?

Is the work-life balance what I’m looking for?

First things first, I’ve seen the following three things crop up time and time again in my own personal experience as possible “two weeks later” deal-breakers that just aren’t always known upfront.

  • What percentage of travel is really expected? When is my first business trip? Is being on the road something that can affect how well I do here?
  • What is the real, honest, number of hours I’m expected to work? (The smaller the company the more important this question is)
  • “If Ricardo likes it then surely it is awesome so no further questions”. Research a company even if your friend works there. Sure you and your buddy worked great together at the last place, but little did you know he loves traveling, getting yelled at, and loud smelly office conditions and you don’t.

Will I fit in, learn, and thrive?

Is this a place where you see yourself being successful after 90 days? Do you see yourself liking or tolerating the people you’d work with and for? Will they help you to succeed?

  • Tell me about your mentoring and training strategies.
  • How many new hires have started in the last year?
  • What success rate are you seeing with new hires?
  • How has the company changed since you started working here?
  • Tell me a story that you are tired of hearing about this place.
  • What are you guys really bad at (i.e. what do you not value)?
  • Does anybody hang out together after work?
  • Has anybody here worked together elsewhere before?

Is the risk/reward situation what I’m looking for?

Before you leave you need to know how stable the company is and where it is on the risk/reward scale between a two person startup and the IRS. This is sometimes as simple as looking around and seeing how many people are in the building and how tired they look, but most of the time you need to dig deeper to confirm your gut feel:

  • How big is this industry?
  • Who are your competitors?
  • Give me a two minute company overview.
  • What are you current business challenges? (Dig deeper if the answers are: grow, become more profitable – how?)
  • When was the last time you had to perform layoffs?

What are they trying to do?

  • Why are you hiring?
  • Walk me through the architecture of your system(s).
  • What do you hate the most, and what’s the things you guys are most proud of?
  • What was the hardest part to get right?
  • What part of the system do you wish you could build?
  • What are you plans to fix your current problems? [Do people agree on the problems and solutions, or are they still up for debate?]
  • What sort of technical debt do you have?

What happens when things go wrong?

How a company acts when things go badly reveals who the company really is. In an interview they may paint the best possible picture, but asking about recent project delays is a great way to get passion and real information out of the interviewers.

  • Talk to me about the last time a project was late (or cancelled), and what actions were performed.
  • When you miss a milestone, do you start to track it more or less?
  • What has been your biggest project failure in the last year?
  • When a project is late, do you ever add people, and is it always the same group of people?
  • How does the client / industry react?
  • When things are behind do you expect more or less individual (vs. group) accountability?
  • Do you perform post mortems?

Speaking of post-mortems, make sure to be able to effectively close the interview by asking them if there is any additional information they need from you in order to make a hiring decision. Then hopefully in a few days you’ll be asked “When can you start?” and positioned with the knowledge mined in the interview you’ll be able to answer.