50 Questions To Ask the Interviewer

From time to time, I have people ask me for advice on how to nail their job interview.

One thing I never get asked is: “What questions should I ask the interviewer?”

In my experience, the questions you ask the interviewer are just as important, if not more so, than the ones they ask you.

The right questions can not only impress your interviewer and show them you’re serious about the job, but they can also get you the vital information you need to make the right decision. Remember: This is a two-way street, and the job interview is also a chance for you to get to know the role and determine if it’s the right fit.

When I was first looking for jobs, I used to ask just any old questions to make sure I was meeting this requirement in job interviews. But after working with a few bad seeds, I take those questions very seriously, because I never want to work for a bad boss or in a toxic work environment ever again.

You should follow my lead, because your boss and internal culture have a massive effect on your happiness, even when you’re not at work. Asking your interviewer the right questions will not only make you a stronger candidate, but will also help you weed out bad fits before you accept a job that isn’t right for you.

In this post, I share all the most pertinent questions to ask that will help you make sure the company and role you’re interviewing for is actually right for you.

Download the cheat sheet: 10 questions you should ask the interviewer during your next job interview

Before you start: Who is interviewing you?

Before you can decide what some good questions to ask an interviewer are, you need to be sure you have a good understanding of whom you’ll be speaking with during the interview. Hopefully, your interviewer will tell you ahead of time, but if not, you can politely ask to get more intel.

Once you know who will be in the room (or on the Zoom interview), you can tailor your questions. In general, there will be three types of people you might meet in an interview:

Your future manager. This is the most common scenario, and many of the questions on this list are relevant. But if you’re meeting with someone who may be your manager in the future, you know you can focus on things like your roles and responsibilities.

Your future colleagues. Sometimes jobs give you a chance to meet people who will be on your team or on the same level as you once you start. Good interview questions for these folks can be about their day-to-day jobs or company culture.

Leadership in the organization. Perhaps the CEO or other members of the company’s upper echelons will be in the interview. If so, ask questions about the company’s history and overall mission, and how you will fit into the big picture if you take the role.

Let’s break this down a bit more and get into some good questions to ask in an interview with each group.

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Good questions to ask in an interview with a manager

Can you tell me more about how your career path led you here?

This question sounds innocent enough, but it can give you a lot of juicy information about the potential job. For starters, you can figure out how long your manager has been at the company—if they’re a new hire themselves, that might be a bad sign that the company struggles with retention. (Though in some cases, it just may be a sign of fast growth.)

If you end working for this person, knowing their personal story and career goals will be a big boost to your working relationship. (It’s a big part of managing up.)

You can also learn more about the kind of work your boss does day to day with this question, and get any idea of what your working life might be like with them. Do they know a lot about the job you’re applying for, or are they less likely to be involved in the minutia of your daily work? Learning their backstory can help you figure out what a job working alongside your manager would be like.

FOLLOW-UP QUESTIONS:

What’s kept you here this long?
Is there anything about this role that’s different from what you expected when you started?

What’s the first thing you’d want me to focus on in my first 90 days?

This question does double duty. It shows the manager you’re already thinking past the interview and into the actual job, and it gives you a real answer instead of a vague “you’ll figure it out.”

If they have a clear, specific answer, that’s a great sign. It means there’s a plan for your ramp-up, and you won’t be left guessing what success looks like in those early weeks. Vague or generic answers might mean the role isn’t well-defined yet, or that onboarding isn’t a priority for them.

This is also a good moment to ask if there’s a formal 90-day plan or review process. Some companies treat the first three months as a probationary period with a real evaluation at the end, and you want to know that going in, not find out the week before.

FOLLOW-UP QUESTIONS:

Is there a formal 90-day plan, or will we figure it out as we go?
What does a successful first 90 days actually look like to you?

What is your team’s biggest challenge currently?

This is another good question to ask an interviewer to make sure there’s a level of awareness within the company. Every company has challenges, even if they are overall successful. A good manager should be able to identify what those are and the plans in place to overcome them. No business is perfect, so if you’re met with blank stares, it’s not a good sign.

Their answers will depend on:

The manager’s awareness of the problem.
The manager’s willingness to be honest.
The seriousness of the problems on the team.

It might be good to ask this question to coworkers, too, to see if there’s a disconnect—another sign of dysfunction.

FOLLOW-UP QUESTIONS:

How long has this been a challenge, and what’s already been tried?
Where would I fit into helping solve it?

How will my success be measured in this role?

This question gets at how much autonomy at work you’ll actually have. Listen for whether they hand you specific KPIs with no real explanation, or whether they’re open to you weighing in on what gets measured.

The best answer treats KPIs as a two-way conversation. You should have a say in the metrics you’re held to, and your manager should have a clear, honest reason for choosing them. If they can’t explain why a metric matters, be skeptical of it.

This is also where you can get a sense of how much trust you’ll be given. A manager who wants your input on your own goals is signaling they see you as capable, not just someone to be managed by a checklist.

FOLLOW-UP QUESTIONS:

How often will we revisit these metrics together?
What does exceeding expectations actually look like, versus just meeting them?

How will I get feedback about my performance?

Candid, respectful feedback accelerates your career, because it’s pushing your skills (hard or soft) to the next level. That’s why this is such a good question to ask in an interview—it will ensure they have a feedback structure in place.

When assessing their response to this question, you want to be sure that feedback comes regularly, not just in a single performance review at the end of the year. You also want to make sure that it’s scheduled—ad hoc feedback isn’t useful, especially when you’re new at your job.

Another good, more specific version of this question could be: Can you tell me about a time you helped someone improve their performance?

FOLLOW-UP QUESTIONS:

How is feedback documented, if at all?
Can you tell me about a time you helped someone on the team improve?

How are raises and pay increases decided here?

This is the direct money question, and you shouldn’t feel weird asking it. How you’re paid and how that pay grows over time should be just as clear to you as your job responsibilities.

The answer will depend a lot on company size and stage. At a startup, raises might be tied to hitting specific milestones, which means the faster you deliver, the faster you get paid more. At a more established company, raises are often baked into an annual review cycle instead.

Either way, you want clarity. A good manager should be able to tell you how raises get budgeted, roughly what past increases have looked like, and what it would take for you to get one. If they’re vague or seem caught off guard by the question, that’s a red flag.

FOLLOW-UP QUESTIONS:

How do you budget for raises?
What was last year’s median raise on your team (in percent)?
How much salary increase could I expect one year from now? Best case, worst case?

Good questions to ask in an interview with coworkers

Note: Customize these questions further based on the team you’ll be on and what the prospective role will be doing.

How do you decide what to work on each day?

This is a simple question that can give you a lot of information. In their answers, your potential colleagues will give you insights into the specific tasks they are working on, and how they prioritize their work.

This will also give you a glimpse into what the management style is like. Ideally, your colleagues will demonstrate that they have control over their workload and how they like to work. But listen carefully for hints that they’re being micromanaged.

FOLLOW-UP QUESTIONS:

Who decides if priorities change mid-week, you or someone above you?
How far in advance do you usually know what you’ll be working on?

What tools do you use regularly, including AI?

This answer will obviously be different for every industry, but it’s an important question to ask. You’ll be spending a massive amount of time in different software and apps to do your job, so make sure you actually enjoy using them (or are at least interested in learning).

If you have a tool preference, keep this in mind. Some teams build everything custom instead of using established software, and if you’re someone who needs reliable, polished tools to do your best work, that’s worth knowing before you accept an offer.

It’s also worth specifically asking how the team uses AI day-to-day. Some companies have fully integrated AI into their workflow, while others are still figuring it out or actively avoiding it. Neither answer is automatically good or bad, but it tells you a lot about how the role might evolve and what skills will actually matter most once you’re in the seat.

If they mention a tool you don’t recognize, look it up and ask a quick follow-up about how they like using it. A team’s toolbox says a lot about how much they know about their own industry, and how much leadership invests in setting people up to do good work.

FOLLOW-UP QUESTIONS:

Has the team adopted any new tools or AI in the last year?
Is there a tool you wish the team used but doesn’t?

How do you collaborate at work?

Everyone has their own preferred methods of communication. Some of us are die-hard email fans, while others prefer instant-messaging apps like Slack—and others just want to chat face to face.

Though you may be willing to compromise on how you communicate and collaborate with your employees, asking this question will not only tell you what channels you’ll be using, but also what some of the expectations are around working hours.

In particular, I like to know if they have specific hours they typically work and what times they’re required to be online and available.

Are you expected to respond to messages in a certain amount of time? How late is too late?

FOLLOW-UP QUESTIONS:

How would you describe the work environment here?
Is the work typically collaborative or more independent?

What do you like about working here?

A long silent pause is a bad response here.

So is…

“It pays the bills.”
“It’s easy.”
“There isn’t a lot of pressure to deliver.”

Instead, you want to hear answers like…

“I enjoy what I do.”
“I have fun at work.”
“I love working with smart, driven, open-minded people.”
“The company values [your department/what you do].”

Every team member doesn’t need to gush over the company, but you definitely want more good answers than bad.

Side note: Glassdoor could also help demystify this question for you as well.

FOLLOW-UP QUESTIONS:

What’s something that took getting used to when you started?
Is there anything you’d change about working here if you could?

How do you measure your progress in this job?

To be successful in your role, you’ll need to have clear benchmarks from day one. This question will help you figure out what those are, so you can gauge whether they’re realistic or not.

If no one on the team is measuring their progress, they’re not improving, which will mean you won’t be improving either. Or if they don’t seem to place value on measuring stuff in the first place, it’s usually a sign of laziness or ineptitude, both of which are negative. It’s pretty hard to change cultures like this, in my experience at least.

On the opposite end of the spectrum, if the interviewer has a good answer to this question, it’s a great sign that they’re a high-caliber team.

A good follow-up question is: “Why are you measuring X?”

If the answer is bloated and vague, be leery. They should have a good reason for why they’re measuring what they are, and if they don’t, you might be in for a rude awakening when it comes time to start work.

Metrics should always yield actionable insights.

FOLLOW-UP QUESTIONS:

What is the overarching success metric for the entire company?
What is your source of truth? (i.e., Google Analytics, Facebook, Intercom, etc.)

What teams do you collaborate with the most?

The bigger the company, the more cross-collaboration.

If you haven’t worked at a big company before, then you’ll likely be weirded out by how many people must buy into what you want to do, even when those people aren’t experts in what you do.

For example, as a marketer, I often work with the product team, the engineering team, and the design team, to name a few.

In the answers to this question, make sure that the responses make sense. In your experience, did they list the teams you would expect to be working with? Or does it sound more like teams are siloed, and collaboration is stifled?

FOLLOW-UP QUESTIONS:

Which team/leader has the most influence on decisions usually?
Which team do you like working with the best? Why?
Which team do you work with the least often? Why?

Questions for leadership

What’s the five-year plan for the company?

This question gets you a lot more than it seems to on the surface. You’re not just asking about ambition, you’re finding out whether there’s an actual strategy behind it, and whether that strategy sounds realistic.

Listen for how they talk about growth. Are they focused on building something sustainable, or is the plan to chase the next funding round and hope it all works out? There’s not one right answer, but you want to know what you’re signing up for.

This is also a natural opening to ask about profitability without making it weird. If the company isn’t profitable yet, a healthy follow-up is asking what the path to profitability looks like, or whether they’re banking on a future acquisition or IPO instead. Company culture tends to take a hit as money gets tight, so this is as much a read on stability as it is on ambition.

If you’re interviewing at a SaaS company, you can also ask about their churn rate as a follow-up. A high churn rate (people canceling their subscriptions) often points to deeper problems with the product itself.

FOLLOW-UP QUESTIONS:

What’s the biggest risk to that plan actually happening?
How has the plan changed in the last year or two?

How would you describe the company culture?

You’re looking for answers that tell you how the company operates and what it values most.

It might be helpful to get the coworker interviewers to answer this question as well, to see if there are any discrepancies.

Sometimes leadership is out of touch with how things work for their employees. Or they just talk the talk and don’t walk the walk, so pay attention to very different answers from employees and leadership here.

Side note: A lot of companies have culture decks today. Google “[company name] culture deck” or “[company name] internal culture.” Or just visit their “about” page, or scroll to the footer and look for pages like “mission,” “values,” or “culture.”

The company values should not only match your own, but they should also be in the same order of importance, only if you want to steer clear of conflicts, of course.

FOLLOW-UP QUESTIONS:

What’s something the company says it values that doesn’t always show up in practice?
How does the culture change as the company grows?

Why did you start/join this company?

You’re listening for two things here: whether there’s a real mission behind the company, and whether this person actually believes in it.

A strong answer connects back to a specific problem they care about solving, and you can usually feel the energy behind it. They light up a little. They get specific instead of generic. A weak answer falls back on the product, the funding, or the market opportunity, with nothing about why it actually matters to them.

If you get the chance to ask this question to a few different people, do it. Compare what a leader says to what a manager or coworker says. If the mission and energy line up across the board, that’s a good sign the company’s “why” is real, not just one person’s pitch.

FOLLOW-UP QUESTIONS:

Has your reason for staying changed since you joined?
What would make you leave?

Tell me about your reporting structure

It would be ideal to see an org chart here if you haven’t already, but if not, you can at least get an idea of the company structure by asking this question.

First, if you haven’t met your manager directly by this point, you may want to ask if you’ll have a chance to meet with them before deciding on the role.

Beyond that, listen carefully for signs of micromanaging in their answer. Is everyone expected to report directly to the CEO? If so, the boss may have control issues and cause major bottlenecks that will be a huge pain when you start working.

FOLLOW-UP QUESTIONS:

How many people report directly to my manager?
How often do decisions get made without input from the people they affect

Interviews are a two-way street

By now you’ve got more than enough questions to walk into any interview prepared. But the more important thing to remember is what these questions are actually for.

This interview isn’t just about convincing them to hire you. You’re also figuring out if this is a company and a role you want to say yes to.

Asking good questions shows the interviewer you’re serious and engaged, and it gets you the information you actually need to make a real decision. Use what you learn here, along with what you already know about your own values and what you want out of a job, to decide if this is the right move for you.

If you’re looking for a role where you can learn, grow and work with great people, request an interview at Vector.

Want more advice on applying for jobs and acing the interview? Here are a few more resources to check out: