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Getting Hired

12 Questions To Ask Your Future Employer

Ever start a new job and realize it wasn't everything you were promised? Avoid the post-hire let down by asking the right questions during the interview.

Job interview prep is often focused on nailing the questions your future employer will ask you, and delivering the best answer. Usually that means running through your answer to, “What’s your greatest weakness?” over and over in the mirror.

Less preparation, however, is given to the inverse (but just as important) scenario: asking your future employer the right questions to get to the heart of what you’ll do, and who you’ll support, at the job.

Finding the right culture fit and team match is even more crucial when the company you are applying to is in the early growth stage: these are the people you’re going to spend the next few years of your life with. You’ll need to be able to be honest, and strategic. Your success in navigating the job interview can affect how well you’ll fit in with your new colleagues. 

So how do you take it upon yourself, as the candidate, to find out everything you need to know about the job you’re about to take—and the company you’re (hopefully) about to become an integral part of? This is your chance to get to know the people behind the mission, find out what’s working, and cover critical ideas about what next steps you’ll take with the company. Your task is to dig in and compare the “dream vision” behind the glossy pictures and mission statements with the real facts.

Your task is to dig in and compare the “dream vision” behind the glossy pictures and mission statements with the real facts.

But people don’t always report their behaviors and ideas accurately. So how do you build a picture of what the company needs—and whether you’re a good fit for the role? And how do you make sure you don’t walk away thinking you’ll have a great job, only to hear silence for weeks later? Ask the right questions.

Know the Job and the Constraints:

Sometimes, especially with a startup, what the company is looking for isn’t too clear. Here are a few key questions to dig into what the company really needs—because your job description may be changing from day to day:

What’s the biggest thing you’re working on solving right now?

Not their mission or the larger company vision—what are the biggest blockers to the company reaching its goals? How are they going about solving this, and what is getting in the way? Ideally, they’re hiring you to solve a specific problem and/or take ownership over a process. How will you know that you’ve delivered? How can you get clarity around what the core functions of your job are? Another follow-up question:

How does this job currently get done?

Get to know what the company is doing to solve its specific problems that relate to your areas of expertise. You want to walk in the door ready to work and not be surprised that about how badly the company is organized.

What could I do immediately to make your job easier? What about my job will help alleviate your workload?

If you get a vague answer to “how does this job currently get done,” try the above follow-up questions. It gets at the same issue, but in a different way.

Know Your Future Peers:

In a study of casual social conversations amongst employees, Lynn Wu at the University of Pennsylvania’s Wharton School found that those who have greater connections with their team members were the least likely to get laid off during hard times.

Those who have greater connections with their team members were the least likely to get laid off during hard times.

Employees who used words like “lunch,” “baseball,” and “coffee” in email conversations and social communications was a greater predictor of longevity than purely objective performance measures. In other words, it pays to get to know your peers.

What’s your morning schedule, and what time do you wake up in the morning?

Getting to know someone’s morning routine will tell you a lot about how they prioritize, organize, and how you’ll work together during the day. Do they start early meetings and want to hit the ground running? How do they spend their free time?

If I could free up time for you to do anything, what would you do with that free time, personally OR professionally?

If you’re interested in accelerating your personal learning and career capital, the collection of skills that make you valuable (as Cal Newport suggests in So Good They Can’t Ignore You), you’ll want to find a company that energizes you and encourages learning, growth, and challenges. You could tire quickly of a job that keeps doing the same thing over and over again—instead, look for a company where people are engaged both in the office and off the job.

What else are you learning right now?

One sign of a healthy organization and team is when people have enough energy to have outside interests. “What are you learning about right now?” can yield answers from “I’m learning how to change my new kid’s diapers” to “I’m becoming a DJ on the side, mixing beats and sharing them on my Trello board.”

This also lets you connect with your team by learning about what motivates them. Get to know whether or not they are an open, supportive culture that encourages the growth of the whole team, or whether the culture is 100 percent company-focused, preferring not to let personal life get too involved.

Know the Organization’s Culture:

We’re not great at reporting our own behavior—so it’s better to ask questions that showcase behavior, rather than allowing your interviewer to paint a rosy picture of an imaginary work environment. Employers are going to want to tempt you with ideals of work-life balance, but asking “What time does everyone go home at night?” can seem like you’re uninterested in working hard.

“What would your last five hires say about the company?”

One of my favorite questions to ask a new employee is “What would your last five bosses say about you?” I got asked this by Mattan Griffel, CEO of One Month before I joined his team, and he explained to me that you can tell a lot about a candidate by whether or not they look uncomfortable about this question. Sometimes jobs end poorly; sometimes there’s miscommunication. In the best world, however, an employee leaves their previous organizations loved by their colleagues, and the boss has nothing but kind things to say—and the company wishes they could have kept them longer. As the interviewee, you can ask a similar question about the organization.

Who are your most recent hires, and have any hires not worked out? Why not?

What you’re looking for is whether they hire and fire quickly, and a deeper understanding of how well the company knows their hires. If things haven’t worked out, learn why—so that you’re more prepared to start the gig and you have more information about what didn’t work before.

How would you feel about me taking risks and experimenting with new processes, if the work results showed up and improved over time?   

Instead of asking if people show up late, stay late, or work from home—you can ask how it would be welcomed if you decided to try to mix things up. I spoke with a potential employer about how to balance my time, and I told him, “I work extremely hard, and sometimes I overwork myself and burn out. As a result, I’ve implemented yoga and meditation sessions, and I take a day to work from home each week. I’ve noticed that my output, performance, and happiness is at an all-time high, so I’d like to implement this at your company.”

By focusing on results and experimentation, you can find common ground to agree on: you’re both interested in trying to get results that haven’t been achieved before, so why not present experiments in how you work to maximize performance along the way? For sure, these things don’t happen the moment you start working, but explore if they’re even possible.

Know the Pain Points of the Hiring Process:

Sometimes a job interview is going great and it seems promising. Yet something still isn’t being said. If you’ve ever walked out of what felt like a great conversation and then been the recipient of silence, what gives? It doesn’t work to just show up with a pretty face and a good-looking suit and smile through the interview.

It doesn’t work to just show up with a pretty face and a good-looking suit and smile through the interview.

Your future company wants to know how you’re going to work, and whether or not you’re going to be a good fit. “I’m trying to find out whether they have self-awareness; whether they are able to be critical; and most importantly, whether they’re able to tell the truth—when it’s difficult,” explains David Reese in a Harvard Business Review article. And if he can’t get a handle on what makes you tick, “I leave the interview wondering: Who are you?”

Don’t let this happen to you. As the interviewee, dig in:

What’s the biggest obstacle you’re facing in fulfilling this position?

Begin to ask your interviewers about how they’ve approached fulfilling the position. The answers may surprise you. When you’re direct, they may respond with clarifying information about when or if you’ll be hired. If the company is waiting for funding—say, from the next round of investment or from improved sales—they might not be able to hire you for another six months, at best. Get a good picture of what they really mean when they say they want to hire someone “soon.”

If you’re being honest, what’s the biggest hesitancy about adding me to your team, and what could I do to alleviate this?

If the interview is going extremely well, this question can begin to take possibilities into realities. I learned this key interviewing tip from Willo O’Brien, a multiple startup co-founder and business owner. The key phrase “If I’m being honest,” can trigger people to peel back layers and reveal more of their inner workings. (It works great as a survey question for product reviews, too).

Know How To Walk Away With a Win:

At the end of conversations, I like to ask people about what would make them happy. I’m not joining a team just to tuck in and perform like a rat on a wheel—I’m here to help affect company culture, create a great work environment, and deliver amazing results. Along the way, I want to encourage people to grow and learn, to challenge themselves, and learn from failure. 

My favorite final interview question is:

What could I do to delight or surprise you?

Rather than make it all about “me,” however, I want to ask the company leaders and team members how I can make their life easier, how I can integrate into their team, and how I can take the work and make it even better. So ask them what would be delightful for them. I’ve asked it over and over again—whether as a consultant or as a corporate employee—and the results are always good.

As a consultant trying to win a gig or a get the upper hand on a proposal, this is a great strategy as well—you can ask your future clients not just what they think they need, but how working together could be surprising, delightful, and a joy for the months to come.


Ask lively, different, and interesting questions to get into the heart of the organization, and to connect with each person on a deeper level. If you can dig into meaty subjects during the interview, the chances are higher that you’ll keep the conversation going—when you join the company.

How about you?

What questions have you asked at a job interview that helped you get the gig?

Interviewers: what questions have left you impressed with a candidate?

Comments (46)
  • juan sanchez

    Very interesting article and full of true statements. Nice!

  • HenryM

    Great list of questions. Interviewers are always praising my questions. The two I usually ask are What is your biggest problem right now and What brought you here and what keeps you here?

    • Sean Blanda

      I really dig “What brought you here and what keeps you here”

  • Amy Blankenship

    Yeah sure people want to know you’ll tell the truth even when it’s difficult. Of course if you do that after being hired, in many places you’ll be fired as a bad fit.

    • Kim

      this is so true. People do not want the truth. I’ve been feeling alone in thinking this. Thanks for posting.

      • Sarah Kathleen Peck

        I think you both have a fair point. Honesty isn’t always easy, and you have to be careful about when and how to convey your points. But I think that if you hide everything (or you’re never honest), then there are also downfalls. How do you balance both?

  • Ross Fazel

    An interviewer recently asked me what trait I saw as my greatest weakness. I said honesty. He said he didn’t think that was a weakness. I said who the hell cares what you think….

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  • Spelunk

    The same questions could / should be asked by a service provider when asking to be hired by a customer. These are the basics – very well stated in this article – that every service should consider when crafting an ideal customer experience. Thank you, Sarah, for writing this piece so well!

  • Guest

    I like when future hires inquire about why I started my design studio… Similar to “what brought you here” but shows an interest in the backstory of the company (nut just its current mission) and lets me speak candidly about what I care about.

  • Gopika

    I like when future hires inquire about why I started my design studio… Similar to “what brought you here” but shows an interest in the backstory of the company (not just its current mission) and lets me speak candidly about what I care about.

    • Sarah Kathleen Peck

      Gopika, that’s an awesome question. It’s a great way to get to know the backstory of a company (and get to know the managing partners, CEO’s, or founders a little bit better).

  • sanjay

    Thanks for the great post.In an interview I was asked, why I have not stuck to one job for more than 3 years?

  • Tony

    Great questions! You may freely ask these questions in the US and may be some other part of the world but how do you justify it considering all cultures globally? I know in many countries, some of those questions wouldn’t be welcomed by employers at all.

    • Shannen Ellis

      Totally agree! Some employers might misconstrued it. But great questions though.

  • cjbaltzley

    Thanks. Some good questions here. I have a second interview this afternoon. I might owe you a drink if I get the job. 🙂

    • Sarah Kathleen Peck

      You’ll have to let us know how it turns out! Good luck!

  • Shannen Ellis

    Thank you for the great questions. Some questions cannot be applied though to other countries. Anyway, I found something helpful to boost confidence, it might help us too!

  • Web Outsourcing Gateway

    thanks for this question and definitely tips.

    the most useful and yet unfamiliar question, in my own point view, is “If you’re being honest, what’s the biggest hesitancy about adding me to your team, and what could I do to alleviate this?” this is precisely the biggest move an employee could ever make in front of an employer yet, it is so alleviating.

  • coxy

    I’m pretty sure that if anyone I’d interviewed over the years started asking these questions, I’d show them the door.

    • Sasha

      Interesting, why’s that?

      • James Walker

        Because most hiring managers don’t like to be questioned. It’s not the idealized world that HR writers think it is out there.

      • Sasha

        So you’re saying your ideal candidate has zero questions for you throughout the entire interview process?

      • James Walker

        I’m not Coxy but I’ve run into managers like him and I can tell you from experience that they could care less about your questions or a “culture fit” unless they want to use it as an excuse for why they didn’t hire you. That simple

      • Banana Ghost

        No. I believe he’s saying that some of those questions make a candidate seem a bit too forward or aggressive while being vetted for a position. It’s good that a candidate is thinking about things like these – but to come out and openly ask me what hesitancy I have in adding you to the team, would give me hesitancy in adding you to the team.

        Also, ‘what time do you wake up’ question? No. Don’t ever ask a hiring manager that during an interview. Ever.

      • Sasha

        Ahh, I see, I see. I both agree and disagree with this — but I think that all depends on both the team and the person being hired as well, and I’m entirely biased when it comes to that question (It’s worked for me personally every time!). In my mind, asking what might make a prospective employer hesitant about hiring you establishes that you’re open and honest, and their answer in turn will let you know a lot about how transparent and honest your working relationship can be as well. But there are a lot of assumptions or miscommunications that can be made when the only contact HR has had so far with them is one resume and, presumably, maybe this one interview, or two at most.

        I’ve used a version of that question in every interview I’ve ever had (my Dad recommended it to me as a teen), and I’ve never not been offered a job afterwards (all 7 I’ve had, anyways). Hard to say if it was all due to that question or not, but I was able to clear up one or two mistaken assumptions through it, which definitely helped.

      • Sarah Kathleen Peck

        These are really interesting observations. I think it depends on context and the person you’re chatting with. Don’t take all 12 of these questions and fire them one after the other — these are unexpected questions to sprinkle into the interview and it’s up to your discretion how to use them. Keep in mind that a lot of these questions are targeted towards small companies, so a hiring manager wouldn’t be in the picture.

      • Sonya Denyse

        We are in the flux between the industrial age and a world where work is being redesigned. Questions that empower you optimize your potential role in a company to help achieve its mission should be welcomed. Good question indicate vision. If the hiring managers goal is to find the best fit for the position, wouldn’t having someone who cares about where they work be welcomed?

      • James Walker

        Way over thinking it. It all becomes easier to understand once you realize the humanity has been removed from the process. You, the candidate, are a “resource” and resources are afforded only enough consideration to be consumed. That’s why they call it Human “Resources”

      • Sonya Denyse

        That is probably the difference between being a bean counter and a world changer… thinking 🙂

      • James Walker

        World changers don’t sit in interview chairs. Think Steve Jobs, Bill Gates and Richard Branson. Best to endeavor to not spend much time in them yourself.

    • Theodorah Manjo

      Yoh I agree Cox like you can’t be asking about their hiring and firing habits, you are nothing but a person taking up their time at this moment.
      Some of these questions would NEVER get you the job. Ever.

    • Szymon

      Of course, some of these questions may be too forward but not all – we cannot generalize. For me it’s look like you don’t want anyone asking you about anything while interviewing – Am I right?

  • Sarah Kathleen Peck

    Feeling like a team is an essential element for me — it’s one of the reasons why I left consulting to go back to a company gig. The team was too good to pass up!

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  • Rayan Umer

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  • 100smilesforeveryone

    I would also add these important questions:

    “What do you like best about working for this company?”
    “What would be the top priorities for the person who fills this position?”
    “What would be the main challenges for the person in this position?”
    “How would the person doing this job collaborate with his/her direct manager and other key employees?”

    Asking questions is definitely not one-sided anymore. Interviewees should flip the script and become the interviewers as well. It shows you’re an above-average candidate, and you also get valuable information about the company and position you wouldn’t get anywhere else.

  • mindofandre

    I think these are great questions for the smaller companies/startups (as Sarah mentioned in a recent comment). For the people that are working on hiring the right people rather than being told they need to straight up fill a position quickly and get back to the grind. And when I think about 99u, I think about individuals/companies trying to build a smart culture and do great things. So I think these are pretty appropriate in the right context as you feel things out during the interview. Perfect for some opportunities I’m entertaining – thanks Sarah!

    • Sarah Kathleen Peck

      Thanks Andre! And thanks for noticing the context — it’s definitely focused on smaller companies, startups, and organizations with smaller teams. These questions wouldn’t all work for every organization (or every person).

  • Nanci

    “Where is the last person who held this position?” If they got promoted, great, it means there’s growth opportunities. If they were fired/let go, it could go either way, maybe they were the problem or maybe the boss had unreasonable expectations. If they left for another company, not great, they probably had a reason why and I have to wonder if I’ll end up doing the same. In the case of he last two you may ask about the person before them. Asked ever since the first job I ended up with after college had a new hire every year because the hours and the boss tended to burn you out.

    • Sonya Denyse

      Great one. Speaks to the organizational history and the history of the role within the organization.

  • reno_gal

    Some interesting questions – would certainly need to be toned down for the UK market. Maybe better for the entrepreneurial arena or ‘front foot’ type roles.

    The comments show that interview style can select a corresponding applicant. Those hirers that want more direct employees will like and select those that ask them. Those that dont wont hire them – that works as a selection process. It depends on the level of job, type of company, industry, market at the time.
    I dont like interviewees that just nod and agree – I like to see knowledge and some positive go get ’em – i want to know i can show them the ropes and that they will get on with it without handholding. Interviews should be somewhat two way asking questions shows youre not desperate.

    But I would never ask or like to be asked personal questions like when do you get up – that would seem like an invasion into their home.
    I also wouldnt ask whats your biggest hesitancy – this is a very negative way; firstly that assumes they have one, or encourages them to think of the negatives – it would be better to swap it round and say something along the lines of – I am really interested this role and think i can bring a lot to it, how can I prove to you I am the right person?

    • Sarah Kathleen Peck

      I think you bring some great insight into cultural differences and ways to phrase the language to make it more effective for different opportunities. This is definitely focused on the entrepreneurial (and American) style of startup-business. Thanks for your additions and insights!

  • Sonya Denyse

    I often tell people to “interview the opportunity” so I LOVE this article. In terms of a team environment, I would ask ” what are 3 words you might use to describe your team?” you can swap out team with “work environment” or anything else appropriate. I might also ask what an ideal day is like in terms of productivity, creativity or whatever the overall goals are.

  • Pieterjan Spoelders

    While I do agree that there are some interesting questions in between I’m afraid asking most of these would really feel too forced..

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