The Best Interview Questions to Ask a Prospective Hire

Interviewing a new employee is sort of like a first date. Everyone tries to put their best foot forward and it can take weeks or months to discover what that person is really like or if they are a good fit. So, to make it easier to find out what a potential new hire is really like before you make that commitment, I have reached out the CarolRoth.com contributor network of business owners, advisors and entrepreneurs to find out their best interview questions. Their answers are presented below in no particular order.

You may notice some similar ideas listed, but I kept them separate, as something in the way one is framed may resonate differently with you.

1. What is Your Passion?

I wish that the questions that were asked to me over the past twenty or so years in the corporate world would be something more than how many words I could type per minute or do you know how to file? If corporations would just take a bit more time to find out about their potential employees, job retention would increase. The simple question of what is your passion would clear everything up immediately!

Thanks to: Warren Bobrow of Cocktail Whisperer.

2. Show Me Your Thinking!

What are the 2 or 3 key improvements that you think we should make to our website?

If they are not fully familiar with our website prior to the interview, they will not be able to answer this question appropriately and this will show lack of preparation and research on their part. If they are, the depth of their thinking, reasoning, creativity and marketing insights will become apparent.

Thanks to: Steven Howard of Howard Marketing Services.

3. The One Question You Must Ask!

The one question is an open ended question that reveals the potential new hires' level of preparedness.
"If hired, how would you make an immediate impact on our business?"

Thanks to: Doug Hecker of 2 Excel Now, LLC.

4. The "Trap"

I have used this many times and it is a really effective "screener" that separates the posers from the real deal. It's a 2 step process:
1. Ask them what they consider themselves expert at and let them really pour it on about how great they are on this or that.
2. Then, ask a hypothetical question that relates to your business about that subject to see if they can apply their expertise to your situation.

Watch their body language - the posers get nervous and twitchy.

Thanks to: William Loeber.

5. Will They Make You Better?

"How could you improve our business in 15 minutes?" It ensures that they've researched your company, and that they'll also be bringing new ideas to the table. Anyone can tell you your company's mission statement. It's the star employees that can tell you what you should be doing better.

Thanks to: Flynn Zaiger of Online Optimism.

6. Why Do You Want to Work Here?

Prospective employees often start asking about salary, time off, vacation and don't ask what the job is all about. I always ask people the "why" question. Why do you want to work here? It's simple, direct and provides a business owner with a wealth of information in the hiring process. It's also amazing that not many people ask this all important question. I'm looking for a creative answer that puts a candidate above others. The answer to this question is part of the key in hiring a new person!

Thanks to: Mark Alyn of Mark Alyn Communications, Inc.

7. The Question That Gets Us

This question is inspired by one Jay Abraham shared with me recently. Whether dealing with a prospective employee, or a potential client, vendor or business partner, ask "What question didn't I ask that I should have?"

The results can give amazing insight. The question that they share reflects their level of confidence, fear, expertise, self-centeredness and so much more! And their answer to the question yields that last bit of information that may sway your decision.

Thanks to: Tara Alemany of Aleweb Social Marketing.

8. Give Yourself an Award

If you were hired here, what award would we all want to give you at the end of a year?

Thanks to: Sally Franz of Sallyfranz.com.

9. What Do They LOVE to Do?

As employers, it should be obvious that the closer in nature the job is to the activities that the employee loves to do, the easier is it to train the new person and have them be self-motivated. After developing a little rapport with the person you're interviewing, simply ask them, "So, what would you spend your time doing if you didn't have to work?" The answers may surprise you, but will give you deep insights into the type of person you have in front of you and what they'll be good at naturally.

Thanks to: Elisabeth Donati of Creative Wealth International.

10. What Would You Do as CEO?

It's one question that will often reveal a great deal about a person's vision and goals for themselves and their potential employer. This question also helps the interviewer to assess if this person sees themselves as more of leader or a follower. With just this one question and the responses that you may receive, you can get a clearer perspective on who this person is in front of you, how they feel about themselves and what they may want to aspire to become and do for your company.

Thanks to: Myles Miller of SuccessHQ.

11. Why Not to Work Here?

We always know why someone wants to work here. They come with polished, often scripted answers - but no job is perfect and every opportunity has potential negatives. This is the candidate's opportunity to show that they have a great understanding for the business, but also that they recognize that no opportunity is perfect - but that they have solutions for coping with those obstacles.

Thanks to: James Hills of James Hills.

12. Get a Writing Sample!

Because writing is a significant part of online marketing and PR (emails, social media updates, pitches to reporters), we require applicants to submit writing samples in the 2nd round of interviews.

We prompt them with some scenarios - such as an email from a reporter, or a tweet from an upset customer - and ask them to write up a response. This teaches us a lot about the candidate's writing and communication skills and gives us info that oral interviews can't.

Thanks to: Kari DePhillips of The Content Factory.

13. Why Do You Want to Work Here?

Why do you want to work here and what contribution can you make to our success?

Thanks to: Jane Blume of Desert Sky Communications.

14. What Would You Do If...?

What would you do if/when a "job specific" scenario happens? Early on in my career, I was interviewing for an administrative assistant position and was asked what I would do if 3 people gave me different "need now" tasks. The answer was ask my boss. The interviewer was thrilled with that response and offered me the job on the spot. Point being- ask something that is real world to the job being discussed.

Thanks to: Heidi McCarthy of Customers First!.

15. Hornet or Honey Bee?

How people get along and resolve interpersonal difficulties is always of great interest to me. This would be my question:

What has been your most difficult or challenging career relationship and what was the result of it?

There can be many layers of skill revealed in the response, ranging from simple problem solving to the way career politics is viewed and worked around.

No matter what the job title is, people skills are always important.

Thanks to: Sheila Van Houten of New Light Consulting Corporation.

16. Fore Warned is Fore Armed

I have all of your strengths; what is your greatest weakness?

Thanks to: Jim Camp of Camp Negotiation Institute.

17. Responding to Overwhelm

The Question: Your alarm didn't go off and the line at the Starbucks is 15 people deep. You have a meeting at 9 am, but you're not sure that you'll make it. You have 20 new emails in your inbox, 2 project deadlines today and three missed calls on your cell. How do you handle a morning like this?

I ask this question because I want to know how people respond when there is "too much to do". I ask the question quickly and expect them to make a fast decision about how to prioritize. It's very telling!

Thanks to: Jessica Oman of Write Ahead.

18. Catching Liars in Your Hires

At the end of the interview, if you're close to hiring the person ask, "What’s the question that I haven’t yet asked you that would tell me what I don’t know about you but should know about you?"

Also, if you think “truth!” before each question you ask, either they will tell the truth even if it’s not in their best interest or it will be obvious when they are lying.

These tools are developed by Gary Douglas of Access Consciousness.

Thanks to: Dr. Kacie Crisp of Dr. Kacie Crisp Coaching.

19. Improvise to Win the Job!

How good are you at improvising and thinking on your feet?
Give me an example of how you have done this in the past?

Thanks to: April Jaffe of Raize your game.

20. Making Them Sweat = Truth

Look for behavior, not knowledge. Asking a management candidate how they would handle conflict between two subordinates will get you the 6 steps to conflict resolution that they learned in school- NOT what they actually would do. Instead ask: Tell me about the time that you handled a conflict, what you did and why you chose that approach? They will pause, think and now give you insight into who they really are! Lies will be exposed. This is critical for high level positions.

Thanks to: Harlan Goerger of H. Goerger &Assoc dba AskHG.

21. Historical Re-Boot

If you had the power to go back and change the outcome of a single event in the entire history of mankind, what would it be and why?

Thanks to: Christina Hamlett of Media Magnetism.

22. Seeing in the Dark

I like to ask, "In a moment of darkness - when a comment taken out of context has been passed around or a project didn't perform as expected or a colleague makes known that they don't approve of your working style....how do you stay in the game and rebound from a failure?"

I am looking for an interviewee who isn't trying to impress me with tackling the problem as much as showing how they keep their head in the game. The key is staying focused and to keep striving.

Thanks to: Leah Goold-Haws of LGH Marketing/Strategy.

23. How's Life?

I do not want "victims" working for me and representing my business. When I ask "how's life?", if the person goes on to complain about their - fill in the blank - and all of the reasons that others have held them back I'm done. If on the other hand, the person is an "owner" of life, excited about whatever new thing they are doing and the opportunity at hand, someone living in the moment, I know that they deserve more of my time and at the very least, my consideration.

Thanks to: Jim Josselyn of Academy of Music and Drama.

24. What's Your Passion?

Passion through service and charity can be a telling question. I would frame it like this:

"Service and charity are both important to our organization; tell me/us about what your philanthropic passion is, where do you give your time through service or other resources through charitable giving outside of religious organizations. What is your passion for doing good in the world?"

This question gives a totally different perspective of the candidate.

Thanks to: Donna Price of Compass Rose Consulting.

25. Interview Question

If you were me, interviewing you for this position, what questions would you ask?

Thanks to: Soul Dancer of Souldancer Network, Inc.

26. Do We Need to Adjust?

Herb Kelleher, founder of Southwest Airlines, advises "hiring for attitude, training for skill." If we were to hire you, what attitude would you bring to our company? What skills would we need to train you on, so you could maximize your contribution to our company?

Thanks to: Marlene Caroselli of Freelance Author.

27. Next Question?

What question would you like me to ask?

Thanks to: Syd Hoffman of All-Day Energy.

28. Fess Up!

Tell me about a time when you really dropped the ball/screwed something up. This is a great question because it gets to their ability to take responsibility vs. shifting blame, willingness to talk about their not so shining moments, what their role was, how they fixed it and how they ensured that it would never happen again. You can not only HEAR the story but watch HOW they talk about it- then, you can evaluate if all fits in your environment/culture.

Thanks to: Julie Bauke of The Bauke Group.

29. Why Here?

I think it's really important to know why a candidate chose your place to work at. So many people apply for jobs and know nothing about the company; I want to know what makes them think that this is where they want to be and I want to know that they've done their homework. You'd be surprised how many people have no knowledge of your company - it was a job - and they applied. So, I always ask: "What can you tell me about our company?" and "What made you think you'd like to work here?"

Thanks to: Kellie Auld of Simply Communicating.

30. The Best Interview Question

If you want a person who is always learning and applying what they have learned/experienced, ask:

Tell me about the last project you worked on, what was your role, and if you had the chance to do it over again, what would you change and why?

Thanks to: Andrea Herran of Focus HR.

31. How Can You Help My Business?

You need to research the company and find a niche you can fill. This goes beyond "Why should I hire you?" An obvious place to learn is the company website, but you also should try to find current or former employees through networking that can tell you about current or anticipated company challenges. You may also be able to find company information on EDGAR filings. In short, the better you answer the question of how you can help their business, the more successful you'll become.

Thanks to: Gregory Gottsacker of North Star Business Systems, Inc.

32. Go for the Goal

Small businesses run on the ability to consistently set and achieve goals. So, one of the best interview questions is this one: Would you please share with me your most recently achieved personal and professional goals, along with the process of how you achieved those goals? This question also gives the small business owner insight as to the thought process and critical thinking skills of the potential employee.

Thanks to: Leanne Hoagland-Smith of ADVANCED SYSTEMS.

33. Your Proudest Accomplishment?

This open ended question gets them talking about the first thing that comes to mind. If they ask if it should be personal or business related say, “Whatever you are proud of,” then listen. There is no correct answer. They will tell you their passions and successes. How does their answer match up with the goals, passions and values of your business? One candidate told me how he took apart his motorcycle and rebuilt it. We were looking for a problem solving engineer and he was a perfect match.

Thanks to: Timothy Lorang of Image Media Partners.

34. Best Interview Questions

What's your "Unique Ability?" Let them brag a little.
"What would the person who likes you least say about you?"

They'll pause as they search for a trait that won’t present them in a bad light. A good answer highlights something that seems negative, but focused properly is a good attribute. An example? Patience—or lack of it. It could be bad in a workplace. But focusing on finishing the job can build your career - someone's got to take charge.

Thanks to: Matthew Hudgins of Mosaic Wealth Management, LLC.

35. Hire for Passion!

I tell my clients that they need to be able to answer this question: "What makes you the absolute best choice for the role?" However, the absolute BEST question for any hiring manager to ask is "What makes you passionate about this job?" If the job inspires them, they will find a way to do great work. If they're passionate, it means that their values are getting honored and the job will provide fulfillment. Hire for passion every time!

Thanks to: Elene Cafasso of Enerpace Executive Coaching.

36. Why You?

What will you bring to the table that sets you apart from the other candidates that are equally qualified?

Thanks to: Harris Glasser of Serving The People Press.

37. The Revealing Question

Whenever I interview candidates, which I do frequently, I always ask them, "Tell me 5 words that a colleague would use to describe you and then, tell me 5 words that you would use to describe yourself."

Thanks to: Dima Elissa of Visual Media.

38. What Kind of Team Player?

It's best to ask "What kind of team player are you?" (Everyone says that they are a team player, but there are vastly different approaches that are engraved in our individual character.)

Thanks to: David Leonhardt of The Happy Guy Marketing.

39. Best Interview Question

What would you do the first week that you are hired?

This question tells me whether this person has the skills to do the job, not just if they talk a good line. It's a question no one else asks.

Thanks to: Ian Dainty of B2B Business Coach.

40. Attitude of Gratitude!

"If I were to offer you this job right now, what would you say?" If the candidate starts to negotiate for money or says that they need to think about it, that is not the employee that I want. If the candidate says YES with no hesitation or shows some other type of enthusiastic response, that is the person I am looking for. I find an "attitude of gratitude" is the most valuable attribute in an employee.
Those who are grateful will always happily give 110%.

Thanks to: Aimee Elizabeth of Author of "Poverty Sucks!".

41. Waiting for Instructions?

I give the interviewee paper, an assortment of pens, and then, ask them to help me design a house. I tell them I can't draw, so they are welcome to make a list, write, etc, instead.
Some people will immediately draw a box. But, I want them to hesitate and then ask me detail seeking questions.
Normally, I have them design a house for 40' tall, blind giraffes. It shows problem solving skills, creativity and that they understand when they need more information, typically before they start writing.

Thanks to: Erica Cosminsky of The Invisible Office.

42. Go for the Jugular

The best interview question for Sales Rep job applicants is: How many President's Club and other over quota awards have you received?

The best interview question for executive and manager job applicants is: What are the three basic elements of effective leadership? Answer: Vision, Employee Interaction and Motivation (Making them feel strong and empowered), and Political Acumen (Getting most employees on your side.)

Thanks to: Leonard Scott of Leonard Scott & Company.

43. Learning Over Earning Any Day

Ask them "What's the next important thing you want to learn?" People who know what they want to learn next are generally self-starters, more focused, and easier to work with (my opinion). Younger employees who value learning over earning have the acumen to do great things for your business!

Thanks to: Mike Wittenstein of Storyminers.

44. Blame Game

It is interesting to ask future job candidates how they:
1. Respond to criticism or, 2. Respond to being blamed for something (a late report, saying the wrong thing, etc.)

These questions create a scenario that tells you how the potential candidate deals with adverse personal relationships in the workplace. Do they support themselves calmly with facts, or do you detect poor self esteem and poor coping skills? It is the soft skills and interpersonal relationships that are key.

Thanks to: Lorraine Justice.

45. Proactive/Reactive Hire

Tell me about an innovation that you initiated, something that you came up with, like an idea implemented or a suggestion to improve something.

Thanks to: Tracey Fieber of Tracey Fieber Business Solutions.

46. Try This!

Work sample testing rocks! When I managed call centers - where you live or die on problem-solving aptitude - the resume and the interview usually told you absolutely *nothing* about how successful they would be. Putting them in front of a computer and saying "Here, try a demo of our product," with a few well-placed questions, quickly and accurately told us who would really succeed.

Thanks to: Rich Gallagher of Point of Contact Group.

47. New Hire Question #1

When interviewing a candidate, I always include this question- how it's answered tells me a lot about the person: What are you NOT good at- where could you improve?

Everyone has things that they aren't good at. Being aware of what those things are, and being willing to admit it to a potential employer, is not easy. When a candidate can admit their shortcomings, and provide a plan for getting better, it speaks volumes about them.

Thanks to: Stephanie Hackney of Branding Masters.

48. Have They Done Their Research?

"What is it that you like about our company?"

Thanks to: Chase Fleming of Communication Studies.

49. Is Your Kitchen Kept Clean?

The very first question I heard at my very first interview was: Do I keep my bedroom clean? I was applying to be a cook at a local restaurant which was a big interview considering the fact that I had no cooking experience. The question I would ask a perspective employee would be: Do you keep a clean and organized kitchen? Believe it or not, a clean kitchen shows a persons' preparedness for responding to situations at work, situations that could make or break a company in seconds.

Thanks to: Dean J Kropp of DJK Productions.

50. Handling Challenging People

One of the most telling indicators of how a person will perform in their new job is to ask them to describe past performance. I like to ask candidates about a challenging situation they've encountered with a customer or fellow employee. Whether they choose an example of dealing with a customer service issue or settling a difficulty with a team-mate, the nature of the example, and how they resolved it, can tell a lot about their character, ethics and ability to deal with stress or uncertainty.

Thanks to: Stephen Smith of Work.Life.Creativity.

51. Start Your Engines!

Incepture’s Staffing Operations Director, Kathy Young, suggests the following question - "How would you build a carburetor?" It may seem off-the-wall and irrelevant (unless you’re hiring a mechanic of course!), but it will reveal the candidate’s honesty, creativity, teamwork and their ability to respond under pressure.

Thanks to: Libby Kelly of Incepture.

52. Through the Looking Glass

“If you were me, what question would you ask yourself? … and then answer it.” This question gets at a few things that you might not get otherwise: 1/ How the candidate thinks and more specifically, how they deal with complexity; 2/ How well they understand the company’s needs; and 3/ It also can yield things that you never thought about. I almost always ask this question when helping an organization with a hire.

Thanks to: Sam Alibrando of APC, Inc.

53. Tell Me Why You Work?

I had a hard time picking one question. There are two that are a mainstay of our process. The first is, “Why do you work?” With this one, we like to find out what a person wants out of life, what motivates them and how we can help them meet those goals; they can be personal or professional. The second question, “How will you meet the success factors outlined in the job description?” gives us a good understanding of critical thinking and how a new team member would approach tasks and goals.

Thanks to: Al Wynant of EventInterface.com.

54. This One Gets You Hired!

Ask the Employer, "What would you like to see me accomplish in a year in order to qualify for a raise or bonus?" This question demonstrates that you're a performance base thinker and assumes that you have the position too - it's a winner! The employer will open up and tell you more about the position, allowing you to further demonstrate your skills and build rapport.

Thanks to: Bert Martinez of Hire and Grow Rich.

55. What's Your Favorite Song?

Everybody has their favorite song that they like to sing out loud to. Music is a universal language and can immediately put an applicant at ease. Talking about music puts most people in a comfortable place and makes it easier for them to answer questions truthfully. The whole idea of interviewing is uncomfortable enough. I'm not there to trip people up; I want to find out who they really are and talking about music lets me do that.

Thanks to: Angel Tuccy of Experience Pros Radio Show.

56. Ask an Open-Ended Question

Our business is based on Customer Service. We don't sell a product, we Deliver a Service! To find out what a new hire might do, I ask, "If your client is upset with you and starts yelling and using profanity, what do you say to them?"

What he tells me he would say or what he says he would do with an irate customer tells me how well or how poorly he would do as our representative. If he handles it well, it will get him a lot closer to his coming to work for us!

Thanks to: Gary Christensen of Christensen's Delivery Service.

57. THE Best Interview Question

Give the applicant a current problem to solve from the job s/he is applying for. Ask for steps s/he would take and how s/he would evaluate success. By providing a real-life situation, you get an opportunity to determine if the prospective hire understands your business and/or has been actively listening to how you have framed the position during the interview. Giving them a current problem to solve also allows you to evaluate their values and how they relate to company values.

Thanks to: Aubrey Daniels of Aubrey Daniels International.

58. Indispensible!

Best Question: What makes you indispensible?
The idea that a worker is best-suited for a job means that he/she isn't easily replaceable since he/she is THAT good. An answer to this question can be a barometer to a candidate's drive, intelligence, innovativeness, quick thinking, problem solving, long term vision and possible future with the company. HOW he/she answers this question with demeanor, body language, humor (or lack thereof) etc. also gives the interviewer added meaningful insight.

Thanks to: John McAdam of Pioneer Business Ventures.

59. What Would Your Mentor Say?

Are you fortunate enough to have or have had a mentor? If I tracked that person down, what would he or she say that you need to focus on for continued personal and professional development?

Thanks to: Charley Polachi of Polachi.

60. WORK?? Really...

I always love to ask potential employees or contractors what is the one job or task that they would do without pay or financial incentive. The answer to this question tells you about their priorities, morals, passion and interests.

Thanks to: S Capri Edwards of AGC Transport & Services LLC.

61. One Question? Thousand Answers

"Why do you want this job?" This question has been around since Adam and Eve interviewed for a gardener. However, the answer often provides more information than both the resume and the rest of the interview combined. If the response focuses on what the job will do for the candidate, the job performance will be reflective of that same attitude. If the response focuses on what the candidate can bring to the organization, both now and in the future, that's the candidate to consider.

Thanks to: Jeanne Rodriguez of Pennico Press.

62. King for a Day

When I read this question for the first time, I knew that the person to ask was Chuck Gordon, our CEO and co-founder. When I approached him with it, he said that there was one specific question that he used to always ask potential new hires and that was "What would you do if you were king/queen for a day with unlimited resources?", but he also said that he hasn't used it in awhile. "I need to start asking it again though" he said, "because the answer says a lot [about that person]", and I have to agree.

Thanks to: Matt Schexnayder of SpareFoot.

63. Surprise Interview Question

An excellent question for an interviewer to ask is, "What have I not asked you that I should have?" Talk about open-ended! This question gives the one being interviewed a chance to highlight something he or she believes is important and relevant to the job and to the organization. The question also demonstrates the interviewer's openness, as well as his or her ability to empower others by unleashing their talents and ideas, both of which are vital to the health and success of a company.

Thanks to: Kimberly Gleason of Kimberly Gleason Coaching.

64. What Did You Actually Do?

The best question to ask is, when you arrived at your current or last job, what did you actually do? No, I do not want your job title or job description. I want to know what you actually did. Walk me through it. Many follow-up questions will give a good comprehensive understanding of the applicant.

Thanks to: Mitch Carnell of SPWC.

Do you have a great interview question that wasn’t included? If you do, please share it below. And as always, many thanks to everyone that contributed to this article!

And if you would like to become a part of the CarolRoth.com contributor network and find out about opportunities to contribute to future articles, sign up here: http://www.carolroth.com/carolroth-com-blog-contributor-sign-up/