Just one more question
When next you’re hiring, don’t automatically resort to the same, old interview questions.

If you’ve ever interviewed for a job — and if you’re reading In Business, that’s highly likely — then you’ve probably encountered some … interesting interview questions.
Some of those may be of the bland, perfunctory variety: “Tell me about yourself.” “Where do you see yourself in 5 years?” “What are your greatest strengths/weaknesses?”
Others may be strange, or purposely intended to see how well you think on your toes: “If you were a pizza delivery person, how would you benefit from scissors?” “If you were a fruit, what kind of fruit would you be and why?” “Do you believe in Bigfoot?” “How honest are you?”
Still others could be downright illegal to ask: “Are you a United States citizen?” “Are you pregnant?” “What is your religion?” “Who are you voting for?”
Whatever the questions, interviewers ask them for a reason — not necessarily a good one — and candidates often dread having to come up with a new spin on an old question that everyone else may have already answered in a similar way. The reasons for asking a particular question may not even matter if the question itself is so complicated or off the wall that any answers given force the interviewer to try to parse whether the candidate is even being truthful or just saying what they think the interviewer wants to hear.
For hiring managers, getting the interview questions right can make all the difference in finding the best candidate for an open position — one who can not only perform the job itself at a high level but also fit well with the company culture. However, not all managers are experienced in interviewing and hiring. Someone has to be your first hire, or perhaps you just haven’t had a reason to do it very often because employees at your organization typically have a lot of longevity. Whatever the reason, not everyone is a seasoned HR professional, and an interview can be just as daunting for the interviewer as it can be for the applicant.
What follows is an examination of some of the most overrated and underrated questions an interviewer can ask, along with insight into why hiring managers should consider tossing or adding these questions to their next candidate search.
Tried and true?
Some interview questions have been around for a long time and interviewers may feel that they have to ask them. However, if the answers don’t give you insight into the candidate, do the questions really serve a purpose?
According to Renee Krueger, a human resources operations services manager at Vorteq Coil Finishers in Oconomowoc, “Personally, I won’t ask — and hate being asked — ‘Where do you see yourself in 5 years?’ If the pandemic and gig workers have taught us anything, it’s that you can’t answer that question with any certainty. A better way to ask is, ‘How do you want your career to grow as you take on this role?’”
Recruiter.com singled out additional questions that may be overrated in the interview process, noting, “Some of these questions are so threadbare from use they can no longer elicit a single authentic insight into a candidate’s personality or skill set, while others were never really all that useful in the first place.”
These questions include:
- What are your strengths and weaknesses? It might work for some people, but if you’re asking the right questions, you should be able to work out a candidate’s strengths and weaknesses yourself.
- Why do you want to work here? Most candidates will have a fluff answer prepared for this question, and it really doesn’t tell you much about the character or work ethic of the applicant. It’s almost a waste of everybody’s time and can be insulting to the interviewee. Instead, situation-based questions can uncover the candidate’s values and character traits to ascertain if they will be a good cultural fit.
- What is your biggest pet peeve in the office? This question only warrants negative answers that don’t lead the conversation anywhere or allow an interviewer to get an accurate read on a potential hire. This question is tantamount to asking, “What do you hate about others?” A better question to ask might be, “What qualities of an office do you think make it most productive?”
- Why should we hire you? The answer you’re going to get here is going to be strikingly similar across candidates — something like, “I believe I would be a great asset to the team. I’m highly motivated, work well in teams, and I’m an achiever.” Instead of this question, ask, “How could you apply your greatest strength to what you would be doing here?”
- Tell me about yourself. This question that’s not a question is supposed to be an icebreaker, but it’s less effective in terms of actually telling the interviewer about the candidate. Since this question has been so overused, the answers are usually scripted and not authentic, which beats the purpose of asking someone to tell us about themselves.
- How would you sell this pen/pencil/object? An old standby in a lot in sales interviews; selling today is based on a solution and is more consultative, which can be almost impossible to determine from answering that question.
Another question that’s not particularly helpful in evaluating a candidate: What would your last boss/colleagues say about you? This question doesn’t really have anything to do with the job being interviewed for, and in most cases, candidates likely don’t know what a former boss or colleague would say. About all you can expect from a question like this is a fluff answer about how they were a great team member and had a positive impact on the team.
Peter Yang, co-founder of ResumeGo and Mock Interview, notes there are four very good reasons why interviewers should stop asking generic questions:
- Generic questions force candidates to lie. “If job candidates are asked, ‘What are your biggest weaknesses?’ what other choice do they have but to lie and make something up?” posits Yang. “No candidate is actually going to reveal that they are terrible at working in groups or that they are so bad at math they need a calculator to do simple addition and subtraction. The underlying issue with many generic questions is that there really are ‘right’ and ‘wrong’ answers to them, or at the very least, a certain etiquette required to answer them that often clouds the truth. As a result, instead of learning more about what an interviewee really thinks, you’re really just learning how well they’re able to muster up a lie.”
- Generic questions are given prepared responses. “It’s no secret that job applicants prepare for their interviews. In fact, they’re supposed to, and the most basic form of their preparation involves getting acquainted with what the most common interview questions are as well as how to answer them. As a result, all you’re getting as a response are eloquent soliloquies that don’t tell you much about what candidates really think. You want to hear genuine responses, not artificial ones.”
- Generic questions don’t screen for top talent. “What’s the point of putting candidates through a tough interview where they’re forced to come up with responses on the fly? A huge part of it is to see if a candidate really has the critical thinking skills required to excel at the job position. Are they articulate, sharp, cunning, and logical? Unfortunately, most common interview questions never let you find out. From questions like, ‘Where do you see yourself in 5 years’ to ‘Why do you want this job,’ none of them gets at the heart of identifying who’s truly the more capable and talented candidate.”
- Generic questions are well-hated and awkward. “If you didn’t know this already, you do now. People hate being asked stereotypical interview questions. These questions force them to lie, to give artificial responses, and quite frankly, many of them are just awkward to answer. What’s someone supposed to say when they’re asked, ‘Why do you want this job?’ Let’s be real now. Pretty much everyone is doing this for the money, yet that’s not an answer anyone in their right minds is going to give.”
Overlooked, undervalued
Overlooked and undervalued may be why the candidate sitting in front of you is looking for a new job, although they’re not supposed to say that.
However, these are the types of questions interviewers themselves should consider asking because they’re more likely to gauge somebody’s abilities beyond the standard line of questioning.
Indeed.com explains these questions can reveal a lot, so the interview should be structured in such a way that you’ll learn as much as possible from them:
- What do you know about our company? Has the candidate done their homework? Do they care enough about the job to learn as much as they can prior to speaking to you? This one will help you quickly identify whether the answer is yes or no.
- Describe your career progression and the story it tells about you. This question focuses a spotlight on the reasons behind the different roles you might see on a resume and the guiding goals and interests behind them.
- Why do you want this job/think you can do this job? This is another question that probes whether the person you are interviewing took the time to learn about your business and genuinely believes they have something to offer. Do they want this job, or do they want any job?
- Describe past team dynamics that either inspired your best work or held you back (or both). This question gives you some insight into what kind of work environment the candidate thrives in and whether your
company culture can provide it. - Give an example of an unsuccessful project you’ve worked on. Personal growth and self-awareness are important qualities, not only for an employee but in people in general. The gist of this question is to identify whether the person you are interviewing is able to learn when things don’t turn out the way they might hope and if they possess that grit and accountability to better themselves and try again. If a candidate can’t name an example or points the finger elsewhere, that’s not a good sign.
Indeed further recommends knowing when to follow up on a candidate’s answer. If the applicant provided an answer that tickled your curiosity or raised more questions, ask them these follow-up questions:
- How did you do that? When talking about professional successes, the interviewee should be able to speak to everything that went into it — from planning, to innovation, to rounding up the necessary resources, to accomplishing it. Having an answer to this question speaks to the ownership they took, and if they included others in their victory, it also speaks to their integrity.
- What was the result? Does this person have the drive to see a project through and follow up on the impact it had? How invested in their own work is the candidate? How interested are they in learning from its success or failure to improve their work in the future? This will help you find out.
Nancy Perry is editor-in-chief of law enforcement publications Police1.com and Corrections1.com. She has interviewed numerous junior editors over a career spanning nearly 30 years, and says one question that continues to work for her is, “What are you looking to avoid in your next job?”
The question is a good one because it accomplishes two things: It allows the interviewer to see if the candidate automatically goes to a negative place, blaming others for their situation, and it also gives insight into possible red flags that could make the candidate a poor fit for the organization.
For instance, if an applicant says they hope to avoid working with difficult colleagues, that could be a problem if they’re applying for a management role where they’ll need to oversee people with disparate personalities that may sometimes clash. Similarly, a candidate who wants to avoid working evenings and weekends may not be right for a venue that hosts a lot of events on evenings and weekends.
However, if a candidate says they’re looking to avoid a workplace that clashes with their personal beliefs, and they’re applying for a job with a clean energy firm and coming from a mining company, that may be a clue that they’re seeking a position that more closely aligns with their passion for sustainability and not simply seeking a payday with a new employer.
On your best behavior
Behavior-based interview questions provide a way for interviewers to delve into how candidates handled past situations. That information can inform their ability to perform in a position. These types of questions often begin with the phrase, “Tell me about a time when you …”
According to the Entrepreneur’s Organization Wisconsin, behavioral interviewing is based on the premise that the best predictor of future performance is past performance and can:
- Save money: Hiring an employee is a significant investment, and a bad decision can cost your business a lot of money. It can also have a long-term effect on a company because below-average employees can lead to disappointed clients and drag down team productivity.
- Provide a better understanding of the candidate: The behavior interview format lets an interviewer gain a more in-depth picture of a candidate in ways that can help determine if they are a good fit for the organization. It’s a way to measure soft skills, personality, problem solving, and work ethic.
- Help predict the employees’ future behavior: Questions like “give me an example of” or “what will you do if” can help interviewers understand if the candidate would approach common situations in a given role in the way the company would want.
Behavioral interview questions can be very effective, but they need to be framed correctly. One important component is how the questions are phrased. The idea is that often typical behavioral interview questions give away the right answers, cueing candidates to share success stories and avoiding failure examples.
For example:
ORIGINAL: Tell me about a time when you adapted to a difficult situation and how you did it.
Expressing the question using this language makes it very clear to the candidate that they are supposed to share a success story about adapting, balancing, persuading, etc.
CORRECTED: Tell me about a time when you faced a difficult situation.
Rewording the question allows a candidate to share success stories that provide details, context, evidence of critical thinking, and much more.
Entrepreneur’s Organization Wisconsin recommends the following sample behavioral interview questions, but cautions that when using behavior-based interviewing, every candidate must be asked the same questions to assess them fairly:
- Tell me about a difficult work challenge you’ve had.
- Have you ever been in an ethically questionable business situation?
- Have you ever had a project that had to change drastically while it was in progress?
- Talk about a time when you’ve had to sell an idea to your colleagues.
- Tell me about a major setback you’ve had.
- Talk about a time where you had to make an important decision quickly.
- Have you ever had a deadline you were not able to meet?
- Talk about a time when you had to adapt to significant changes at work.
- Have you ever had to convince your team to do a job they were reluctant to do?
- How have you dealt with an angry or upset customer?
If a candidate’s answers are vague, ambiguous, evasive, or don’t fully address the question, interviewers should ask follow-up questions triggered by the response.
Don’t discriminate
The Wisconsin Department of Workforce Development notes that one of the purposes of the state’s fair employment law is to encourage employers to evaluate job applicants on the basis of their qualifications rather than on their membership in a particular class to which they may belong.
Under section 111.322(2) of the Wisconsin Statutes it is unlawful to print or circulate any statement, advertisement, or publication, or to use any form of application for employment, or to make any inquiry in connection with prospective employment which implies or expresses any limitation or discrimination based upon a person’s race, color, creed, ancestry, national origin, age, sex, disability, arrest or conviction record, marital status, sexual orientation, military service, or use or non-use of lawful products away from work.
The key to understanding what inquiries might be unlawful is to ask only questions that will provide information about the person’s ability to do the job, with or without a reasonable accommodation. Keep in mind that if it is unlawful to ask the applicant a question directly, it is also prohibited to ask the same question as part of the pre-offer reference checks.
It is reasonable to assume that all questions on an application form or in an interview are for a specific purpose and that decisions are made on the basis of the answers given. In deciding if a question is lawful, the employer should determine whether the information being sought is necessary. For example, why is it important to know a person’s age, or their ability to speak Spanish? If the answer does not provide job-related information or determine a person’s qualifications, it may be better not to ask. Questions which do not produce information that helps the employer choose the most qualified applicant tend to raise questions as to the employer’s motivation for asking the question.
It’s a remote possibility
Ever since the COVID-19 pandemic drove many organizations to a virtual work environment in March 2020, the rise of fully remote or hybrid work arrangements has accelerated. While some companies have called workers back to the office in the years since, many others have embraced remote work, and when surveyed, workers overwhelmingly respond in favor of maintaining at least a partially remote workplace.
When it comes to interviewing candidates for a remote job, ask, “In office, hybrid, or remote. What is your ideal model?” says Jason Willborn, president at SustainableHR PEO in Madison. “If the position offers a flexible work environment, it’s great to see their ideal model. I have found many employees like to come into the office one to two days a week to get the social interaction and fun the office environment brings.”
With that in mind, there are questions interviewers should ask candidates who will be working in a remote or hybrid setting to better ensure the candidate is truly a good fit for that specific type of work environment:
- Have you worked remotely in the past?
- What types of remote/distributed team tools and software have you used and how did you use them?
- What is your approach to maintaining effective communication and collaboration with a distributed team?
- How do you manage your time and stay organized?
- How do you keep yourself motivated and engaged when working from home?
- What’s the key to making sure a project is successful when working remotely?
- Tell me about a time when you had to adapt to change.
- Tell me about a time when you had a conflict with a co-worker.
- Tell me about a time when you weren’t sure how to do something. How did you go about seeking out information?