I reached out to scholars, business leaders, entrepreneurs and hiring managers to find out what are their favorite and most interesting question they like to ask interviewees.  Not only that but they have also provided the reasoning and thought behind the questions.  Situational, behavioral and even lines of disruptive questioning are all included. As this article contains a great depth of knowledge, please use the table of contents below to jump to a question that interests you. The downloadable pdf is here.

Great Interview Questions To Ask Interviewees:

  1. When is it okay to bend the rules?
  2. What would you do in a difficult work situation?
  3. If you’re falling behind and a client or employee needs you to help them with something, how would you respond?
  4. How would you deal with a difficult co-worker?
  5. Tell me about a time that you took the lead on a project and had to influence others to work with you?
  6. Tell me about yourself?
  7. How would your previous employer rate you from 1-10?
  8. What kind of sound do you think describes you?
  9. Can you teach us something in 5 minutes?
  10. What do you value in your work relationships?
  11. How would you explain your career to your mom?
  12. What is your ideal culture to work in?
  13. What would you change is you could go back?
  14. What isn’t on your resumé that you feel is important for me to know?
  15. What’s the worst fight you’ve managed between two subordinates?
  16. How you like to run meetings. Have you changed how you’ve run meetings in recent years?
  17. Why did you leave your last position?
  18. What are you passionate about?
  19. What was the color of the receptionist shirt?
  20. Please describe how to make a paper plane with just words?
  21. If you could write your own job description, what would it say?
  22. Tell me about the time you failed to reach your goal?
  23. When did you make a bad decision?
  24. A disruptive line of questioning
  25. Outside of work, what’s a new skill or habit you’re currently working on to improve yourself?
  26. What cause are you passionate about and how do you take action on it?
  27. What is your dream job?
  28. If you were given a million dollars to start up a company what would you do?
  29. What fictional character do you feel best represents you and why?
  30. Tell me about growing up, what was family life like?
  31. Everyone has a vision, what’s yours?
  32. In our business, we need to be perceptive and read people. How do you read me?

When is it okay to bend the rules?

For example, when I ask, “When is it okay to bend the rules?” The answer should be never. If someone says they would make an exception for a reason, I would go ahead and say to myself, This is probably not someone I should hire. If they say, “Only if the leader allows this,” that would be the only other reason I would consider that applicant. I like to ask situational questions pertaining to a person’s character because I don’t want people coming into the job thinking it is acceptable to bend the rules or be unethical. I want someone that is loyal and trustworthy to my company. This answer is very important because it can directly reveal if they will be honest.

What would you do in a difficult work situation?

For my second question, “What would you do in a difficult work situation?”; From the answer, I would expect to learn whether or not they will have patience, wisdom, and leadership skills in handling difficult questions.. Some people answer nervously on the spot or might not be able to think of an answer, in which case, I can ask them to give me an example of where this might have happened, so they will be able to answer easier. I can then use that example as substance for making my final decision. Character is so important.

A lot of people can be trained on certain positions at your workplace, so if their degree doesn’t necessarily match what you’re hiring for, that shouldn’t be as big of a deal, depending on how intricate the job is. When hiring, finding someone with good character is like finding gold. Of course, you obviously want to factor in intelligence, as well. However, everything else, as far as job training, usually can fall into place with someone with good character and moral standards.

If you’re falling behind and a client or employee needs you to help them with something, how would you respond?

Lastly, for my third question, “If you’re falling behind and client or employee needs you to help them with something, how would you respond?”; I would expect to learn how the potential new hire will handle working under pressure, but most importantly, their willingness to put others before themselves. I would hope for them to say they will help someone out no matter what kind of pressure they are under.

I would have to say that these are my three favorite questions to ask. Finding out certain characteristics of the potential new hire beforehand is not always something that is done. However, it’s probably one of the most determining factors for me because it gives me some foresight on what kind of worker they will be.

Aside from being the founder of the calendar productivity tool Calendar, John Rampton is an entrepreneur, investor, and startup enthusiast. 


How would you deal with a difficult co-worker?

Looking at the big picture, behavioral questions look for examples of things you’ve experienced in the past, while situational questions are seeking examples of how you would do something given a specific scenario.

How would you deal with a difficult co-worker?  In this situational question, the interviewer is attempting to find out if you have the ability to diffuse and prevent potential drama among team members. A good answer would be – “I would refrain from engaging in harmful activities such as gossip and negativity and remain positive in all dealings with that individual. If the situation became difficult to manage personally, I would seek advice from my supervisor on what to do specifically.”

Tell me about a time that you took the lead on a project and had to influence others to work with you?

In this behavioral question, the hiring manager wants to know how collaborative you are and how you influence people to work with you to accomplish common goals. Give examples of what you’ve done and how you were able to get others to go along with your leadership. If you’ve never been a lead on a project, discuss specific team activities or examples from leaders you’ve followed that you would emulate given the chance to lead a team.

Tom McGee Tom McGee, GM/VP Sales & Marketing Division for executive search firm Lucas Group

Start an interview with open questions, then move to more specific questions.
Start an interview with open questions, then move to more specific questions.

Tell me about yourself?

As a former hiring manager at two different ‘Fortune’ ranked companies before entering academia and eventually becoming a tenured management professor, I regularly used open-ended questions of this sort at the beginning of an interview. And since there’s really no right answer, it’s generally a low-stress way to relax applicants and get them talking.

But while there may not be any right answers, there are definitely subjects that wise candidates would avoid during an initial interview. For example, if an applicant is recently divorced and is now the primary caregiver for an elderly parent with Alzheimer’s disease or has two pre-school toddlers at home, those would generally be topics to avoid during that first interview. So given that caveat, what is a potential employer really looking for? In a single phrase, hiring managers are searching for organizational fit.

As a general proposition, organizations seek people who can help them grow stronger. Thus, they want folks who will solve problems, not create them.

So as much as possible, I looked for applicants who discussed the relevant transferable skills and related work experience that they could bring to a particular job, a work team, and the overall organization. Further, answering while weaving in the notion of enjoying challenging work and the sense of accomplishment gained for a job well done also earned high marks during my evaluations.

But, on the other hand, I always expected the whole truth: folks who over-embellished important facts were routinely discovered down the line since my organizations (like most, these days) did thorough reference checks and background investigations!

Timothy G. Wiedman, D.B.A., PHR Emeritus Associate Prof. of Management & Human Resources (retired), Doane University


How would your previous employer rate you from 1-10?

Our favorite line of questioning is the following:

  1. Will your previous supervisor or boss provide you a reference?
  2. If yes, what would they say about you and your work performance?
  3. How would they rate you on a scale of 1-10?
  4. What, if anything, would they say you could have done to get to a _____ (next highest number)?

This line of questioning has several uses. One, can they even get a reference? If yes, great. If no, why? No usually indicates an issue and definitely something I want to know about before considering hiring someone. I don’t care how many HR policies are in place to prevent me from learning something of substance about this candidate, if they were a rock star, their previous supervisor would want me to know. Bosses like helping their former superstar employees succeed and do well, so there’s really no reason the answer to this question should ever be a no if the candidate is worthy of a second look.

Secondly, probing about what the supervisor would say about their work performance and how they might improve digs into the candidate’s emotional intelligence and ability to take another person’s perspective, which usually translates well on the job in any interpersonal situation. It also challenges them to consider their weaknesses in front of an interviewer whom they’ve typically been trained to only speak of their successes and accomplishments.

This is a tough spot but brings up the chance to learn about the candidate’s values, sense of humility and how realistic or practical they might be.

It’s really one big question and can elicit a lot of information about their experience, their achievements, and about who and how they are as a person all at once.

Founder and CEO of The Hire Talent, Fletcher Wimbush, has interviewed over 8,000 applicants.


What kind of sound do you think describes you?

Our favorite personality question by far is “what kind of sound do you think describes you?” The question immediately stumps most applicants at first and it’s one where you can’t throw out a canned or rehearsed answer. It’s open-ended enough for applicants to show their personality (words can count as sounds too! One applicant just said “driven”.) but also a strange enough question where people really need to think about their answer.

Can you teach us something in 5 minutes?

A more technical interview question we ask is “teach us something in 5 minutes”. It allows the applicant to demonstrate how quickly they can think on their feet while also giving us some insight into their knowledge base and what’s “at the forefront” so to speak. We find it’s a much better gauge of professional and personal interest – lots of applicants have taught us some really cool things such as origami or a quick rundown of Gaussian distribution.

Michael Sheen, Hiring Manager: inteliKINECT 


What do you value in your work relationships?

No one comes into an interview saying they’re a terrible team player.  This question gets people thinking and talking.  I’m looking to see what relationships they choose to talk about as well – managers, peers, clients, etc.  The answer draws out true insight into how they play well with others.

How would you explain your career to your mom (or someone that is totally unrelated to this industry)?

There are two things I’m looking for in this answer:

  1. The ability to take something complex and make it simple.  This is a good measure of their ability to communicate clearly with others.
  2. An understanding of what they view as the core of their work and whether it aligns with the core of the role I’m recruiting for.

Lisa Barrow is the founder of Kada Recruiting, a digital and creative recruitment agency. Also former Director of Client Adoption at Monster.com


What is your ideal culture to work in?

I frequently ask interviewees what their ideal culture to work in is. What I expect to learn from this answer is to see if the potential employee would be an ideal fit within the company.

What would you change is you could go back?

I also like to ask candidates about a particular action they took in the past that he or she would change if they could go back. The reason I ask this question is because I am interested in finding out a person’s experiences. While a resume will often boast the candidate’s achievements, I prefer to discover the potential employee’s grit in overcoming diversity and challenges.

Steven Azizi Business Owner – Miracle Mile Law Group 


What isn’t on your resumé that you feel is important for me to know?

My favorite question for interviewees: What isn’t on your resumé that you feel is important for me to know?

The goal here is to find any synergies that might be overlooked if a candidate has tailored their resumé to the position. For a smaller company, this can be incredibly helpful because you might need generalists to help the company grow at first. I asked this during our most recent round of hiring and it provided extraordinarily helpful information on two occasions.

One candidate pointed out that they had a passion for video editing, and had been practicing on their own for the past several months. While this wasn’t directly related to the position, the management team had recently expressed interest in expanding our video marketing capabilities and that skill could be very valuable to the team. Another candidate prefaced their response with I know this is going to sound cliché, but… and described that they were a hard worker. They were right – it did sound cliché at first, but after considering the tone of our interview up to that point (and the fact that they were the only candidate that made that claim) it left a lasting positive impression.

Tony Mastri – Hiring Manager, MARION GroupTwitter


What’s the worst fight you’ve managed between two subordinates? How did you have them resolve their conflict?

A great candidate will actively work to manage through conflict on their teams. If they’re able to find a way to mitigate negative feelings or behaviors, they do, and if they can’t, they assist team members in coping to the best of their ability. The right candidate isn’t afraid to enlist the help of their boss in monitoring and improving team dynamics and can provide thoughtful input to help resolve the situation.

Dealing With Conflict Questions Help You Understand A Candidates Charachter
Dealing With Conflict Questions Help You Understand A Candidates Character: kabaldesch0 / Pixabay

Describe how you like to run meetings. Have you changed how you’ve run meetings in recent years?

A great candidate will have a basket of tools and tricks that they have developed over time to help accomplish the work at hand. No one tool is right for every purpose or need, so the candidate should show that they are open to experiment over time and seek to learn from others what works best to achieve desired outcomes.

Marc Cenedella, CEO at Ladders, a leading job search site. 


Why did you leave your last position?

One question I’ve really enjoyed asking over the years is less skills/experience focused and more critical thinking related.

One mean question I liked asking was “Why did you leave your last position?”. I like to ask that as the last question. Then I ask if they can provide me a list of references.

What I expect to learn is whether they were being truthful with their original answers. Usually, I can tell this just by reading facial signals and body language.

A lot of people have a tough time being truthful about how they left their last job. Personally, whether they were fired or quit isn’t that important, what is important is that they are truthful while applying with me.

If they lied about how they left their last job it will usually be detectable when you ask for references. If the applicant happens to lie and also has a good poker face, the truth usually comes out when references are provided late or incomplete, which would indicate an attempt to hide something.

Rudeth Shaughnessy, Retired HR Professional & Volunteer Director at Copy My Resume


What are you passionate about?

My favorite interview question to ask a candidate is, Other than your family, what are you passionate about? Whether it’s their Sunday night bowling league or their sons Boy Scout group, they need to be passionate about something. If the candidate is not passionate about anything, he/she will not be passionate about working for my company.

Gene Caballero Co-Founder – YourGreenPal.comTwitter


What was the color of the receptionist shirt?

As simple as this question may seem, over 60% of candidates fail this question. The main aim of the question is to test a candidate’s attention to detail. In the nervousness leading to an interview, candidates tend to be surprisingly oblivious to their surroundings.

As any Candidate selected by my firm would very likely handle delicate engineering apparatuses, it is pertinent that they are able to pay attention to minute details.

Please describe how to make a paper plane with just words?

Though not technically a question, this instruction reveals how well a
candidate can describe just about anything to either a fellow professional or a layman. This is a skill that also comes in handy for sales executives and installers of our products.

When answering this question a candidate must display the ability to explain complex procedures using simple sentences.

Joe Flanagan is the Lead Project Engineer and hiring manager at Tacuna Systems


If you could write your own job description, what would it say?

After 6 years of recruiting, I’ve realized that the best interview questions are not the initial question posed, but the follow-up questions after you receive an initial response from the interviewee. Why you may ask? The follow-up questions allow me to peel the layers back and see the person’s true colors. This is where you’re able to genuinely identify the interviewee’s skill alignment and culture alignment.

One of my favorite questions is “If you could write your own job description, what would it
say?”

As the interviewee responds, I make sure to follow up and ask:

  • Why does that matter to you?
  • Tell me more about your interest in contributing in those functions?
  • What makes you feel confident that you would be an asset in the way you just outlined your ideal job?

I have found that these questions get the interviewee out of ‘interview mode’ and lend them to honestly reflect on their skills and desires. It is important to consider what their responses mean about them as an individual: work ethic, core motivating factors, where they get their satisfaction, natural leadership tendencies, and many more hard skills and soft skills.

Ashley Irvin is the Growth Talent Manager of Remedy Review 


Tell me about the time you failed to reach your goal?

I like to ask questions that uncover people with high potential which is very important for our line of work.

What this question does is shows whether the candidate is working from a victim mentality (which most people tend to do) or whether they will do whatever needs to be done to keep going, even when things seem incredibly challenging.

Some examples of poor answers:

  • It wasn’t my fault
  • I had to quit because family/life/job got in the way.
  • I couldn’t do it because of xyz….

All of these answers to me say that given enough obstacles, the person will quit before even attempting to find a new path.

Good answers are:

  • Although I hit the wall, I still kept trying to find a solution
  • Everyone told me it couldn’t be done, but I kept on going
  • I don’t give up easily and I am certain I will find a solution one day

What I’m really looking for when I ask this question is to see if the person is visibly uncomfortable but they never resort to blaming other elements for the failure. This is a great indicator of high potential. These individuals also frequently never admit defeat, but rather see the ‘failure’ as a temporary obstacle that will be resolved at some point in the future.

When did you make a bad decision?

Tell me about the time when you had to make an independent decision which ended up being the wrong one getting you in hot water with the boss?

This question tells me a lot about the candidate’s ego and whether they take responsibility for their actions or if they become really defensive.

Poor answers to this question include vague situations like: 

Oh yes I made independent decisions all the time and some were right, some were wrong but I can’t remember exact details right this moment > Candidate has clearly never made any independent decisions. 

I made a decision to start working with a new client but I made a mistake and didn’t sign Terms and Conditions before accepting the work which caused a lot of problems. I had a stern talk down from the manager and since then I insist that I am made aware of when I’m doing something wrong – because I don’t know it otherwise > This particular answer simply shifts the blame onto someone else rather than taking responsibility for own actions.

Good answers: 

I once had to take over the department while my manager was dealing with a personal issue. I was dealing with a lot of responsibility and made a huge accounting mistake. I realized the mistake and owned up to it. When the boss returned, I accepted the harsh criticism because it was my mistake after all. But since then I’ve made sure to triple check everything to ensure the mistake never happens again.

The boss wanted me to create a brand new website for the company. While I was working on it, I decided to get a new web hosting service but I didn’t communicate this to the rest of the IT department to create a backup of the old site just in case. This resulted in the old website being taken offline so we were left without a web presence for a whole month. I got a lot of criticism and blame for this but it was my responsibility to inform everyone which I didn’t do. Since then I implemented a workflow software into the company that avoids these sort of mistakes happening even when people are not around to have a chat –
they get a notification about the task and everyone is aware of what’s happening. >Both of these answers speak to the person’s lack of ego and willingness to admit their mistake and implement changes to prevent issues from happening in the future.

Deeyana Angelo, Managing Director of Blahtech and Market Stalkers


A disruptive line of questioning

  • How much is eight times nine?
  • Can you write cursive?
  • How long can you go without checking your cell phone?
  • Name a state you have never visited?
  • Name three cities located in that state?

As a behavioral and marketing psychologist, my approach is totally different from the ‘same old – same old ones from HR. Plus many hiring managers have never been formally trained to interview qualified applicants.

Do the above questions and tasks appear easy? They aren’t. Try them yourself. Ask a coworker, one of your best employees, your spouse, even a neighbor, etc., to imagine they are a job applicant for any position of their choice. Administer the questions above to see how well they fare. The results may surprise you.

Would you hire a person who checks their cell phone every 12 minutes? Not me!

Give the applicant a pen and pad with the following directions, “Using a
minimum of five sentences. Yes, you may use more than five, Why do you want
this job?”

I want to see how the applicant organizes his/her thoughts, uses grammar and punctuation, etc. as he/she is going to be communicating with clients/customers.

Dr. Elliott B. Jaffa 


Outside of work, what’s a new skill or habit you’re currently working on to improve yourself?

In my experience, people who are self-motivated, proactive and productive are always doing things to improve their lives. Go-getters are not stagnant and satisfied with the status quo – they are active and enjoy challenging themselves to learn new things, to develop beneficial habits and achieve goals.

Robin Salter, Owner of two businesses, seasoned freelance writer and CMO of a tech startup called KWIPPED


What cause are you passionate about and how do you take action on it?

We want to understand if the candidate is not only a role fit but if they’re a culture fit. As a social enterprise, we’re for profit, for purpose, therefore if they aren’t actively passionate about a specific cause, then they will lack the motivation of our bottom line. You can have the strongest salesperson, or the most detail orientated operations manager, but if you don’t find the right culture fit, then we know that they won’t be interested in going the extra mile.

Lauren Ott, Chief Kits Officer: Kits for a Cause


What is your dream job?

I personally find that this question has the ability to show what their goals are and what is important to them. Asking this question also has the ability to see if their passions align with the company and the company’s future goals.

If you were given a million dollars to start up a company what would you do, who would you hire and how would you make your company different from the competition?

This question allows the interviewee to showcase their abilities for strategic thinking and pushes the interviewee to think on their toes.

Gina Curtis, SHRM-CP, aPHR, Executive Recruiting Manager, JMJ Phillip Group 


What fictional character do you feel best represents you and why?

When new hires answer this question they are demonstrating quick and analytical thinking, creativity, and the ability to have a little fun. Their answer also provides insight into how they see themselves and their personality.

Claire Shaner manages the HR Software Blog at BestCompany.com


Tell me about growing up, what was family life like?

I like to ask the candidate’s a few questions that they likely haven’t prepared for—it helps me to see how well they can think on their feet.

For the question “Tell me about growing up, what was family life like?”, I’m looking to see how well they tell a story.

Everyone has a vision, what’s yours?

This helps me determine how they see themselves: Do they have goals? What passions will they pursue?

In our business, we need to be perceptive and read people, usually over the phone. How do you read me?

This question helps me understand how well they deal with being ‘put on the spot,’ and how perceptive are they. Do they take risks with their answer “you look like you could be demanding and impatient etc”, or are they obsequious “you’re really successful and smart”?

Martyn Basset, CEO and Founder of Martyn Bassett Associates a Recruitment Firm


Great Interview Questions Summary

Well, I hope that was useful, if you liked this article or if you have any great questions of your own you would like to share, please leave a comment below.

Lastly, a huge thank you to all of the esteemed contributors to this article.

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Barry's 25 years of experience with Silicon Valley Corporations such as IBM, Compaq, Hewlett Packard, Hewlett Packard Enterprise & DXC Technology enables him to share his knowledge of succeeding in today's professional corporate environments and develop a great work life for yourself.

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