This is a big collection of questions I've gathered over the years that have proven useful when interviewing. Remember, in any interview you're trying to get to know the company and the people you might be working with as much as they're trying to get to know you. Maybe more.
You wouldn't ask anyone all of these questions. Some of them are simple mechanics. Some of them are only appropriate for certain types of companies. Some of them help you most when you've already got a whiff of org smells. They're all handy to have in your pocket, though. Usually, after you've read the role description and had a phone screen you should have a pretty good idea of which questions to highlight.
I've broken them out by subject matter, with some notes on things to look for and avoid.
And if you'd like more questions for director-and-above positions, Jacobian has a great list.
What's the onboarding process like? Do they have one? How well-defined is it? Do they have a "buddy system" or other mechanisms to help you get ramped up, or do they just let you sink or swim?
In the first 60 to 90 days of employment, what would be my most urgent priorities? Helpful for getting past the position description to the real expectations of the work. Plus the first 90 days are critical.
What is the one thing I absolutely must get right the first year? Similar to the above question, this helps you get a sense of what your success criteria would be as well as how well the employer has defined the role. This one can also help get a better sense of the real priorities, which may differ from what the role description indicated. If they don't have clear answers to either of these questions, the role is probably poorly defined and not set up for success.
What does success look like for your customers for someone in this role? A great question to help get a sense of how user-focused the organization is.
What are the key accomplishments you’d like to see in this role over the next year? This one's pretty much the inverse of the prior, but can be useful to compare and contrast responses.
What type of people are successful here? What type of people are not? Pay close attention to this one. You can potentially pick up a lot of red flags for homogenous, non-inclusive, bro-type cultures. The phrase "culture fit" could be a warning sign.
How do you determine if someone is a poor fit for the company? Same as above, they may tell you more than they mean to about what they value (and what they don't).
If an employee does something harmful that isn't a fireable offense, how do you handle that? What steps do you take to create a culture of accountability? They absolutely should have a plan for this. If they don't, any number of toxic-but-not-fireable behaviors are not being addressed.
Is there any sort of institutionalized way of dealing with plateauing or preventing burnout? You should hear something about rotation of duties or location, sabbaticals, etc. In other words, a real plan for avoiding burnout, not empty platitudes.
How does internal communication work? How does the company communicate with itself, and is that effective This can be a really telling question. Are company communications scattered? Leaked out? Top down? How does it work? Does it work?
Is it easy to move to other divisions or offices? Warning: the interviewer could infer that you are a difficult teammate and like to jump around.
Are there catered suppers? This sounds good. It's not. In any properly functioning organization, you should be home for supper.
How many hours a week does senior management work? Do they put in 80-hour weeks? If so, run away.
What is the company’s policy on work/life balance? How does that work out in practice?
How much vacation do people get? If there's "unlimited" vacation, how much vacation do people normally take?
What holidays are observed? Some companies do not observe federal and state holidays. For parents, this can be a real problem since schools usually do. If so, you may have to use a vacation day for your child's holiday.
Do people work on the weekend?
Do people check in when they're on vacation?
What is your remote work policy? Why is that your remote work policy?
Does this position require travel? How often?
Is it possible to take sabbaticals or unpaid vacation?
How many hours do people work in an average week? Because seriously, if the job can't be done in 40 hours, something is probably wrong.
What is the rhythm to the work? Is there a time that's “all hands on deck” and everyone pulls all-nighters, or is it pretty consistent throughout the year?
What is the policy on alternate work schedules? Is variablity okay, or is everyone expected to be on the same schedule? In modern orgs, especially distributed orgs, asking everyone to punch the clock at the same time is backwards, at best.
What time do people normally leave work? What time do they normally start?
Would I need to be on call? How often?
How often are there emergencies or times when people have to work extra hours? Should be near zero. If not, it's probably a sign of either faulty DevOps or faulty management.
What is your turnover rate? How many people were hired last year and how many left? Over the past 2-3 years? What is the average time people stay? What are you doing to improve retention?
Are the company’s managers inclined to call employees at home with questions or comments? If so, that's bad. Doubly so if they'll call at night or weekends?
How many layers of company managers or executives does one have to go through to get approval for a new idea?
How are disagreements solved? What happens when personalities clash? You're looking for a real, equitable and fair plan here, not a handwave-y answer.
Given everything you like about the company culture, what failure modes do you think that it creates? Are those potential failure modes or have you seen them happen? How do you try to guard against them? Cultural choices can have downsides, too. If the person who's answering you has been in the company for a while and can't give you a good answer, either they're unwilling to give you bad news about the company, or they're not very thoughtful about the culture and its failure modes.who
Tell me about a situation where someone raised a concern about DE&I or ethics? How was it handled? If not, have there really not been any? Is management listening?
Tell me about the organization demographics, particularly leadership. Bad orgs don’t know or get defensive; good orgs are open and transparent; great orgs share what they’re doing to improve.
Tell me about your effort to attract a diverse pool of candidates.
Tell me about your efforts to retain a diverse group of employees. This one is particular useful when paired with the previous.
Tell me about a time when a challenge or suggestion from a person of color was acted on in their favor? How long ago was that?
What happened the last time an employee who wasn't a white cisgender male critiqued something your organization had done?
What metrics are you currently using to track DE&I?
What specifically are you doing to drive greater diversity in management?
What benefits do you expect from increasing diversity among leadership?
What benefits do you expect from increasing diversity across the org? The workplace may be challenging, but it should never be threatening. A manager who intentionally fosters a sense of acceptance and respect can be the reason you love your job.
How transparent is your salary and compensation data? Outside of government the answer will almost always be "not at all" but good orgs will at least have a sense that's problematic and talk about how they deal with it.
Am I The Only One [in the demographic or under-represented group I identify as a member of]? If so, how do you plan to do to ensure that I am welcome, included and equal? Follow-up: where do you anticipate challenges? Incorrect answers include blinking in confusion, saying "everything's fine and we don't see why we'd have to do anything in particular", and "you're not the only one; we have a [person] in a $other_role!"
Do you have a standard insurance package that covers trans health care? Even if you yourself might not use the insurance package, this still gives you good insight into their commitment to inclusion.
Do you offer paternity leave, or just maternity leave? If they only offer maternity leave it can say a lot about the roles they expect women to play.
Most/all of my interviewers were men. Can I speak to someone else on the team to hear more about their own experience? Does the team lacks diverse perspectives?
How are your teams structured? What is the management structure like? How do the two usually interact?
What’s the biggest challenge the team has gone through in the last year? Does the team currently feel optimistic about what's next? Useful for getting a sense of team morale and working conditions.
Is this a new role? If so, follow up with more questions about how the company plans to get buy-in for this new role and support the people in it. If not, see if you can learn more about why the person left. Best case is they were promoted up, meaning this role can lead to similar opportunities for you. This can be useful to understand how well-defined the position is and if it's a position set up for success.
How does the organization reward employees? Is it a star system / team-oriented / equity-based / bonus-based / golf-clap-based? Does it reward individual performance? Team performance? Is the reward tangible and real? How does the company demonstrate to an employee that they are an asset to the company?
What has you most worried? What keeps you up at night? A competitor? Something else?
What’s one thing that’s key to this company’s success that somebody from outside the company wouldn’t know about?
What do you wish you had known when you joined this company?
What would you say are the company’s strengths? Alternately, what would you say are the company’s weaknesses? It can be illuminating to flip these traditional interview questions back on the company.
What is the company’s current strategy for generating new business? What is the company’s strategy for maintaining existing business? This speaks to the viability of the business model and is particularly useful for startups.
Are you profitable? if not, how does this affect what you can do? What's your planned timeline for becoming profitable? Again, particularly useful for startups. Don't ask a publicly traded company this. It will just show you didn't do any research on readily available information.
How do you make money? Again, mostly for startups, but can they explain the business model in a way that makes sense?
Are company financials transparent throughout the company? What about salaries? (see the DE&I section). This is another question that you probably don't want to ask a publicly traded company, because the financials should be public record. If you're curious, you should probably have already checked.
How much are you planning to hire in the next year? If it's a large number, ask the follow-up: How do you plan to hire and onboard that many people?
How does the company usually solve problems: through committee, group meetings, individual meetings or management only? Helps get a sense of where they're at on the consensus-driven to top-down continuum.
How are important decisions made and communicated? Are they dictated top down? Are ideas from anyone welcomed? If so, in what scope/context?
How does sales / operations / technology / marketing / finance work around here? Groups other than the one you’re interviewing for -- the interviewer should have familiarity with those groups, and should (hopefully) speak well of them.
Do managers regularly hold 1:1s? What about skip levels? What sort of topics are discussed?
Who would I directly report to? Honestly, In some cases, this question can help you get a better sense of the org chart and where you'd be on it. It can also be a clue on whether the org is hiring you for a specific team, or just putting you in a pool of new hires to be farmed out as needed.
What’s your (or my future boss’) leadership style?
How do you know if people are comfortable giving you candid feedback? How do you fix it if they’re not? Does your future manager value feedback and want to know what's not working? Hopefully, this is something they've thought about.
How do you nurture psychological safety in your team?
How does work get assigned?
How often do inexperienced people get to work directly with more experienced people? And how so? Pairing, or something else? How does it work?
How do you balance support and feature development?
Tell me about your cross-functional teams Do they have dedicated designers? Product owners? QA? Technical writer? Dev manager? How cross-functional teams are built tells you a lot about what the company values enough to put on the team.
How often do you have meetings? Are there scheduled/standing meetings? How much time should I expect to be in meetings Remember, though, that for some positions (especially senior positions) meetings are a core component of the job.
When something goes wrong, how do you handle it?
What kind of tools are provided by management to help an me do my job? (machinery, computers, office supplies, etc.)? How often is this equipment updated?
Are employees encouraged to go speak at conferences? Do you cover travel to conferences?
Does your company support continuing education? If so, how (and how much?)
In what other ways do you support career development?
Does the company routinely provide training, either internal or external, for new technologies such as software updates or best practices?
Does the company allow employees to pursue their own training path To what extent?
When was the last time you promoted someone on your team? How did it happen? How are they likely to handle it when you want a promotion?
Tell me about a time you supported a direct report leaving your team or company for the benefit of their own growth? A supportive manager cares about your goals, not gluing you to your seat. The very best managers realize when it's time to move you up, even if that means moving you out.
Can you tell me about how the interview process is structured? How many interviews are there?
What’s the timeline for making a decision on this position? When should I get back in touch with you?
How is performance evaluated? What criteria does the company use for performance reviews? Are these criteria documented? If not, how do you ensure fair and equitable performance reviews?
How often can I expect job performance to be reviewed by management?
Are raises based solely on job performance reviews? If not, what else is a factor?
Do you stack-rank employees? If yes, run away. Only trash companies stack rank employees. When they said "we only hire the best" they neglected to say "and then we'll treat at least half of them like dirt, by design."
Can you tell me about a time when you've had to let someone go?
If this is an exempt (salaried) position how much overtime do you assume I would put in without compensation?
If this is an exempt (salaried) position, am I required to track all my time? If so, how? And if it's not hourly, why?
What is the salary you expect to pay for this position?
Is there a company/employee bonus structure and if so, how does it work?
How often do you offer above asking? Can you speak with someone who got such an offer?
What information is shared with the employees (revenues, costs, operating metrics)? Is this an “open book” shop, or do you play it closer to the vest? How is information shared? How do I get access to the information I need to be successful in this job?
Who are the heroes at your company? What characteristics do the people who are most celebrated have in common with each other? Conversely, what are the characteristics that are common to the promising people you hired, but who then flamed out and failed or left?
How many people are directly or indirectly involved in creative decisions?
What kinds of tasks are routinely demanded of by management beyond the original job description?
Does the company require a prospective employee to sign a non-complete contract? If so, in a few words please explain how restrictive it is. Is this non-compete contract negotiable?
How is the office space physically organized?
Is it clean? Well kept?
Are employees expected to pay for basics (like coffee)?
What version control system do you use? How do you track issues? If the answer to either is "we don't", that's very bad.
What's the process for code review? Bonus points if they can point to documented guidelines for behavior in code reviews.
How do you make sure that all code is understood by more than one person?
How do you find bugs in your team's code? Testing? Something else?
What happens when you find a serious bug in production code? If they say this doesn't happen, that's a warning sign.
Who is responsible for doing deployment? How often do you deploy?
How do you think about code correctness?
Is there a written roadmap all developers can see? How far into the future does it extend? How closely is it followed?
How/when do developers talk to non-developers? Is it easy to talk to the people who will be using your product?
Can I see some code the team I'm interviewing for has written? From an open-source project, for example.
What's your approach to technical debt?
Do you contribute to open source projects? Which projects? Which teams work on open source? Do you work mostly in the community or do you have a private fork?
With many thanks to all who have contributed to this list