10 Awesome Interview Questions to Really Get to Know Job Candidates

Question MarksThe last few weeks I’ve been focused on hiring a new team member. Although time-consuming and laborious, it’s one of the most important things I do and is one responsibility a leader can’t delegate.

I have two main goals when conducting an interview: 1) Assess the candidate’s skills and abilities to do the job, and 2) gauge the candidate’s personality, attitude, values, and beliefs to determine if she will be a culture fit. (And not necessarily in that priority order. I would rather hire someone who is a good culture fit that has the aptitude to learn the job, than hire someone with great technical skills who is a bad culture fit. The culture will chew them up and spit them out every time, meanwhile, your life will be miserable managing the person and the fallout created.)

I try to accomplish the first goal through behavioral interviewing. Over the years, my leadership team and I have honed in on a list of behavioral interview statements/questions that align with the key competencies of the position for which we’re hiring. We look for specific accomplishments from the candidate that demonstrate she has the relevant transferable skills that will likely make her a success on our team.

For the second goal—to determine if the candidate will be a culture fit—I ask questions designed to get below the surface. I want to move beyond the standard, interview response clichés, and get to know the candidate on a more personal level. I want to learn about her motivators, demotivators, personality, and instinctive responses to the highs and lows of the job. In order to do that, we’ve come up with some slightly off-beat questions. Granted, you can only learn so much about a person in an interview, but we’ve found these questions to be pretty insightful. Feel free to use them at your own risk!

  1. Tell me your story. This is probably the most generic of the questions we ask, but it’s helpful to get to know the candidate on a personal level. Asking the question in this way leaves the candidate wide latitude in what she shares, which I find telling in regards to her level of vulnerability. Does she talk about her family or just herself? Does she include any personal information or does she keep it focused on her career?
  2. Let’s play a word association game! This is actually multiple questions wrapped up in one. We have chosen several key words that relate to different aspects of our culture, organization, and the job itself. We ask the candidate to share her first response upon hearing the key word, and then we ask her to expand on her answer. The rapid fire nature of this question and answer exchange helps us assess the candidate’s instinctive response and thoughts to the word/situation at hand.
  3. What is the biggest misconception people have about you? This question is designed to probe the candidate’s level of self-awareness and her willingness to be honest and vulnerable. The first impression we have of someone can often be a misconception, and I’m interested in knowing if the candidate has enough self-awareness to understand and manage the way she is perceived by others.
  4. What do you not want to be doing in five years? Rather than asking the standard “What are your goals over the next five years?” question, we flip it around and ask what the candidate doesn’t want to be doing. It gives insight into the type of work or environment that will be demotivating to the individual.
  5. What are three words your coworkers would use to describe you? Whether we realize it or not, each of us has a brand image at work. I’m interested in knowing if the candidate is aware of her brand image, as perceived by others, and if it’s a positive one.
  6. What are your biggest pet peeves at work? It’s amazing how revealing people will be when you ask this question. Their eyes will light up and they’ll rattle off several things that get under their skin. If those irritants are common in your workplace, you’ve just received a heads-up that this particular candidate may experience extreme frustration in the job.
  7. Who are your biggest role models in life? This question gives me insight into the candidate’s upbringing and values system. Does the candidate have positive role models? Does she credit other people with helping her along the way or is she self-focused? This question can open many doors of conversation in the interview that allow you to learn more about the candidate.
  8. Why should we not hire you? I want to see if the candidate has a realistic view of their skills and abilities in relation to the job requirements. Seldom is there a perfect job candidate and I want to see if she is authentic enough to admit she still has some areas of growth.
  9. What would your biggest critic say about you? We’ve all received negative feedback from time to time. This question probes the candidate’s level of self-awareness to see if she is vulnerable and authentic enough to admit it and to help me understand how she has dealt with it.
  10. What is your biggest regret? If you couldn’t tell already, I’m really interested in getting to know the candidate deeper than surface level niceties. A genuine, heartfelt response to this question often tells me more about the candidate’s character and maturity than any other question we ask.

There you go, ten awesome interview questions to help you really get to know your job candidates. Feel free to leave a comment and share your own awesome interview questions.

29 Comments on “10 Awesome Interview Questions to Really Get to Know Job Candidates

  1. Pingback: 10 Awesome Interview Questions to Really Get to Know Job Candidates | « The Corporate Sensemaker

  2. Randy, great list – I don’t think ‘awesome’ is an overstatement at all!

    Thanks for sharing

    • Hi Brigitte! Ultimately I don’t know if a candidate is telling the truth regarding the biggest misconception people have about him/her. However, I have found most people to be genuine and honest and what they share helps me understand the kind of first impression they give to others. For example, I’ve had people say things like…
      + People notice my reserved nature and think I’m stand-offish
      + My bubbly personality often gets mistaken for not being professional and serious
      + Since I look younger than I am, people often assume I’m inexperienced

      Those kinds of responses give me a feel for how the candidate may come across in his/her interactions with clients, which is quite important to me. In the end I think the usefulness of that question depends on the circumstances and needs of the position.

      Take care,


      • Hi Randy, thanks again. I really thought about this question quite hard and all I could do concerning myself is guess work, therefore nothing I’d want to say in an interview. Just for the records: I like reserved personalities because they are often challanging and there is nothing wrong to look younger that what your passport says 😉 Have a wonderful week.

  3. What about biggest regret? That is a very personal question. How do you answer that question andremain professional?

    • Hi Mary. You’re right, asking someone about their biggest regret is highly personal. The way the candidate responds speaks to their level of authenticity and willingness to be vulnerable.


  4. Hi Randy,
    Did you run these questions by your organizations HR department? I recently attended a HR seminar and was told to keep all interview questions about business. So, question 1 was a no-no because a candidate can provide information (personal information) that should not be considered.

    Always trying to protect the company,

    • Hi Mary. You bring up an important issue. It’s important to make sure you abide by the proper legalities when conducting interviews. To the best of my knowledge, there is nothing illegal/improper about these questions. “Tell me your story” is a statement/question similar to “Tell me what you like to do outside of work” or “Help me get to know you as a person.” You aren’t asking the person to tell you their age, religion, sexual orientation, marital status, or any of the other protected areas of employment. If a candidate voluntarily offers that information, that is their choice.


  5. Great set of questions. Very useful. I think over the last few years, understanding the attitude and behaviour is as important/even more than doing technical competency checks.

  6. Its good.. Different way of understanding the candidate in few minutes..
    Helps to assess one’s self if not done already..

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  8. Hi Randy, thank you for the nice article! It is all that one can’t get from school / college. “Tell me your story..” type of questions has really helped me short list most appropriate candidate. Thanks!

  9. I understand what your trying to accomplish but I think your some of your questions have underlying assumptions of what you believe they will show. In a interview setting how are you to judge say a candidate’s response to why we should not hire you. Are you going to make a statement like well I know the skills of applicant 6 and they weren’t realistic or applicant 5 was overly harsh about his skills when they are quit good. So why guess, spend the time to interview candidates (ie more than a single 30 minute interview) well

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  11. Reblogged this on Management Matters and commented:
    Here’s a terrific post from Randy Conley with interview questions you may want to consider using, especially for your management candidates. I recommend you choose two or three to start–using all of them in one interview could mean a conversation lasting hours!

    • Thanks Pat! To your point about using all of these questions in one interview….I’ve done that, and you’re right, it does take a lot of time! (But the conversation and the learning are fascintating!)


  12. I had an interview today, and it was called a “getting to know you meeting”. It was about 10 people around a table in a conference room at a healthcare provider for a position as Desktop Support Specialist.

    The participants were CIO, IT Manager, Service Desk Supervisor, several techs, a Clinical Manager and a couple other I forget their roles but not too consequential, I think. Everyone had two questions, but I’ll just list a few. I’ve never been asked questions like this before.

    The questions were as such:

    If you were a hot dog, would you eat yourself?
    (I answered of course with mustard and relish which evidently was something Will Farrell said and he wanted to know if I was familiar with it, I guess, but I wasn’t, I just happen to say what came to me naturally)

    When you go shopping do you make a list and check off items as you get them, and when or if you do, do you feel better when you check items off?
    (OK, so I said I always recommend a list, but my wife says she knows what to get and doesn’t need one, and I mostly just do what she says, but I like a list so we ensure we get everything we need. As far as feel better, no checking things off is procedural, not emotional)

    If you were a Microsoft Office program, which would you be and why?
    (I answered Microsoft Access that way I could build relationships, but later I thought of PowerPoint because I like to make a great presentation. – geek humor huh? lol)

    If you could get rid of a state, which would it be and why?
    (I answered New York because I don’t think soda should be taxed. I want less tax and more capitalism. Now this answer is problematic because it somewhat exposes my political perspective, and that could easily be viewed as a negative. I honestly was at a loss to answer this question so that’s what i went with, and it was an honest answer. All my answers were true and honest. You want to get to know me, well, here you go.)

    Are some rules made to be broken or there could be a reason someone wouldn’t follow a law or rule?
    (I said sure there can be mitigating circumstances that it would be reasonable to break a rule or law such as driving above the speed limit to get a loved one to medical care in an emergency.)

    OK, so you get the point. It was rather abstract in nature, and I think people were just asked to provide a couple questions that they thought would help get to know someone. I laughed and made it a fun and friendly atmosphere. I’m not shy, so I speak up in a deliberate, but hopefully easy going manner. I think that answers one of your great questions above about self perception.

    This was my second interview, so we will see how it goes!
    (BTW, I have no job, so I had plenty of free time to write this 🙂

  13. Effective approach to get a comprehensive idea of a good candidate but time consuming.

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