Top 25 Worst Interview Questions - Don't Waste Your Time

Some interview questions are awkward. Others are downright illegal. Some of the worst interview questions come from well meaning people who may not realize their questions are ineffective or possibly in violation of anti-discrimination laws.

Protect yourself during the hiring process by knowing which questions to ask and which to avoid. See what these business owners and career experts found to be the 25 worst and even illegal interview questions to avoid asking.

If you’re still hiring, consider using Indeed to find job candidates. You can get $50 in job ads to boost your free postings with Indeed, our recommended job board for small business owners.

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1. Tell me about yourself.

Colin T. McLetchie, PCC, BCPP, President, Five Ways Forward

Here you are in a room with someone you’ve known for 10 seconds, you have their resume and have likely Googled them or looked at their LinkedIn, and the best you can do is, “Tell me about yourself”?

This question is awful for two reasons: It demonstrates a lack of interest, skill or preparation on the part of the interviewer, which doesn’t leave a good impression on the candidate; interviewees are already nervous and this question is so open ended no one knows where to begin. It almost always leaves the interviewee needing to ask a follow-up question like, “Where would you like me to begin”?

Fit Small Business HR Insight: A far better question to ask during your recruitment process is, “Your education and experience caught our attention. That’s why we wanted to meet you. Tell me something about your background that you feel we should know as we consider you for this position.” Then just listen.

2. What would you tell me about yourself growing up?

Mr. Asa Leveaux, Chief Strategy & Revenue Officer, Leveaux Group, Inc

I’ve been asked this question and would never ask this because it doesn’t speak to the results that someone can provide or what personality traits they have developed as an adult that would impact their job.

Fit Small Business HR Insight: This question risks being seen as discriminatory if the candidate should disclose any childhood challenges, disabilities, religious background or even the location of where they grew up. Better to ask, “tell me about why you chose this career path?”

3. I’m interviewing 6 other people this week for this job; why should I hire you?

Vicki L. Myoda, Senior Consultant, PI Midlantic

You’re asking the candidate to compare themselves to other people about whom they know nothing; how can they answer that? Instead, ask: “Based on our discussion of this position and what you’ve learned about our organization, tell me how your experience/education/personality can help us.”

Fit Small Business HR Insight: Focus on the latter part of the question only. Why should we hire you? Or how do you see yourself adding value to the company in the first 90 days? But no comparisons please.

4. Out of the three of us (interviewers), who would you rather work with?

Rhys Jenkins, Social Media Manager, Bowen Eldridge Recruitment

First impressions count… “Out of the three of us… who would you rather work with?” Putting a candidate in this position is unfair and just cruel. Another example is “What size shoe are you?” Apparently it was meant to be a joke around being the right fit, but the candidate was just weirded out.

Fit Small Business HR Insight: Putting a job candidate on the spot has one possible outcome: they will exit the interview and realize you’re not nice people, and the company is not a great place to work. It’s a lose-lose.

5. What is your biggest weakness?

Ellen Jovin, Principal, Syntaxis

I despise this question. Why would anyone tell you their worst flaw at an interview for a job? For one thing, their biggest weakness may well be really embarrassing. Maybe they eat with their toes or compulsively steal beef jerky from gas station convenience stores or have 53 cats.

Asking a question that will almost surely elicit a lie sets a bad precedent: it encourages dishonesty between interviewer and job candidate.

Fit Small Business HR Insight: Yep, what she said.

6. What were you earning at your last position?

Steve Silberberg, Fitpacking Fat Loss Backpacking Adventures

Why in the world is that pertinent? The only reason people ask this is to lowball you. Or if your answer is too high, they’ll eliminate you from consideration because they’re not going to offer that much. It is a horrible, undignified, irrelevant eliminator question.

Fit Small Business HR Insight: Yikes! Asking about compensation history may soon be illegal. Never ask about prior salary. When negotiating compensation at the time of hire, a candidate is free to tell you what they hope to be paid or even offer their salary history as an example, but asking about it is a big no no. Paying an employee based on prior salary rather than paying for what the job is worth has contributed to wage gaps for women and minorities.

7. If you were a song, what kind of song would you be?

Sonja Hastings, Sales Recruiter, Optimal Sales Search

It’s creative, sure. But what is inferred from the answers has little to do with on-the-job performance. Clever answers have their charms but are often not worth trading for highly skilled employees who lacked the ability to be quick on their toes with sharp answers that day to an irrelevant interview question.

Fit Small Business HR Insight: This kind of question may have its place at a fun corporate outing or team building event, where questions like these make people laugh as they get to know each other. But we agree with Sonja that it adds no value in a job interview other than to make the candidate squirm.

8. If I give you this job, how much money are you going to make me?

Rob Weatherhead, Ad Agency Consultant, RobWeatherhead

Not only is this nearly impossible to answer with any accuracy, it completely turned me off the interviewer and the company. It gave the impression I would be a profit generating commodity and that the interviewer was purely self interested.

Fit Small Business HR Insight: Interviewers should try to be more professional and ask instead, “how have you been able to grow revenue in prior positions?”

9. What would your worst enemy say about you?

Tim Shanahan, Registered Principal, Compass Securities Corporation

What would your worst enemy say about you? It’s a stupid question and even more stupid to answer.

Contributor #16, Yvette La-Garde, CEO, VitaMedica, agrees:

In general I think it’s best to shy away from ‘negative-baiting’ questions. With this one in particular, however, it just brings up an opportunity for a person to fabricate a story. From my experience, companies that capitalize on the strengths of their employees have the most success. Instead of asking what their worst enemy would say about them, ask “how would your best friend describe you?”

Fit Small Business HR Insight: We couldn’t agree more.

10. What was the worst thing you have done in your life?

Joanne Douglas, Owner, Clean Affinity Cleaning Service

I have been asked a hilarious set of questions, like what was the worst thing you have done in your life? What have you been doing lately before this interview? If you could be someone else for a day, who would you be?

These are probably the funniest I’ve heard so far because all these questions do not relate to the job post in any way, and they are also very personal questions. I don’t understand why answering these questions would make the employer’s decision faster.

Fit Small Business HR Insight: Interviewers probably think they’re creative with these questions, but job interviews need to focus on job skills, requirements, and cultural fit. So, ask about the job for goodness sake, and leave the party questions till the weekend.

11. Describe how to wash a car

Shanee Hunter, Owner, HR Philosophy

During an interview for a engineer position, the general manager went off script and asked the candidate to describe how to wash a car. This completely caught the candidate off guard and he stumbled to answer. I asked the GM afterwards what point he was getting at with this question. His purpose was to see how detailed and process oriented the candidate was.

Fit Small Business HR Insight: While behavioral interview questions that test how people would react in specific situations are fine, they need to be related to the job. The interviewer could have said “I want to see how you would walk through a process step-by-step, so describe how you would develop a testing process for a new miniature drone.”

12. Do you smoke, drink or use drugs?

David Waring, Co-Founder, Fit Small Business

This question has become riskier with the advent of legalized drugs in many states, and should the candidate be on a medical marijuana prescription for back pain, it may even cross over into the prohibited area of asking about a disability.

Fit Small Business HR Insight: It’s okay to ask the interviewee if they would be willing to undergo a pre-employment drug test, but in that case, you would have to drug screen all applicants for similar jobs. You can’t cherry pick and only drug screen the folks who look sketchy to you.

Peter Yang, Co-Founder, ResumeGo

13. Are you single?

“Are you single”, was asked by a man of an attractive young lady at an interview for an entry-level sales job. He very likely was hoping to take her out on a date, but it is completely inappropriate to move the discussion in that direction during a job interview.

Fit Small Business HR Insight: This question is not only likely to get you in hot water for discrimination, but for sexual harassment as well. Asking about marital status is a no-no. Attempting to date your job candidate? C’mon.

14. When do you plan to retire?

This was asked of an older gentleman, presumably to understand whether or not he planned on taking his job seriously or simply wanted to coast until his retirement. While this may be a valid concern, it’s completely inappropriate to ask the question in this way during an interview.

Fit Small Business HR Insight: According to the Age Discrimination in Employment Act (ADEA), which protects those over 40 from employment discrimination, this question is illegal. Instead ask: Can you tell me about your experience with (topic)? It may also be okay to ask ‘how many years do you see yourself working here full time?” if that’s a standard question you ask all job candidates, but asking an older-applicant about when they plan to retire? Um, no.

15. How honest are you?

It goes without saying that any candidate would claim their honesty during a job interview, and this question could come off as standoffish and destroy any rapport between the interviewer and the interviewee.

Fit Small Business HR Insight: This question is not illegal, but if you want to know how honest someone is, ask them to tell you about a time they had to make a difficult ethical choice. You can also run a background check, or call their references. But don’t make them try to prove something unprovable.

Beware of These Next 10 Illegal Questions

The remainder of our examples will focus on down-right illegal interview questions to avoid. We’ll explain why each is a problem so you can avoid tip-toeing into this dangerous dialog with prospective candidates. Some are obvious, others not so much.

Yvette La-Garde - Illegal Interview Questions

16. Any question involving race, sex, gender, religion, or family.

Yvette La-Garde, CEO, VitaMedica

From my experience, I advise to always play it safe and keep the questions on a professional level. If you happen to bring up one of these topics (race, sex, gender, religion or family), it could trigger an emotional response, or it could just supply you with information that doesn’t help in making a hiring decision.

Fit Small Business HR Insight: The Equal Employment Opportunity Commission (EEOC) prohibits discrimination in hiring on the basis of protected characteristics, such as race, gender, and religion. These questions shouldn’t be asked even of current employees because workplace discrimination laws protect employees beyond hiring – including for promotions, termination and even job training opportunities.

17. Are you gay, transgender, or what?

The Equal Employment Opportunity Commission (EEOC) also outlaws discrimination in hiring on the basis of sex, including sexual orientation or gender, so questions like this could get you in legal trouble. And anyhow, this question cannot answer whether or not your interviewee will be a good employee.

Alternative: If you’re trying to verify the person’s work history, you could ask, “Have you worked under another name?” Otherwise, skip the question entirely.

18. Do you have kids you need to pick up from school?

Some employers are rightly concerned about worker’s ability to work specific hours. But asking about family status also violates the EEOC because it’s seen as discriminatory. Instead ask: Do you have any limits on the hours you’re available to work Monday through Friday? Or, are you available to work overtime? Or can you make 10 sales calls per day? (Keep the focus on the job requirements and productivity, not the employee’s family or parenting status.)

19. Are you going to need any special days off for your religious holidays?

This question, as innocent as it may seem, intrudes on the interviewee’s personal beliefs and is dangerously close to EEOC prohibited questions about religion. You cannot pry into someone’s religious background, and you can’t use that information to determine their worthiness to do the job.

Alternative: If scheduling is a concern you could ask, “Are there any days or times when you cannot work?” But, to avoid discrimination, you would need to ask this of all candidates, not just ones you think may have a specific religious concern.

20. Have you ever been arrested?

In some states, you can ask about convictions, but not about arrest records, In either case, you’re risking an EEOC violation if you discriminate against individuals in a protected class such as minorities like blacks and hispanics who may be over-represented in the criminal justice system, especially if their criminal background has no relevance to the job duties.

According to the law, you are innocent (even if you’ve been detained by the police) unless you’ve been convicted of a crime. So before asking any questions about convictions make sure you check with your state employment agency. At the time of publication, 29 of 50 states ban asking about convictions — including Connecticut, Hawaii, Illinois, Massachusetts, Minnesota, New Jersey, Oregon, Rhode Island, and Vermont which prohibit these questions from even being on the job application form.

Here is what you can ask instead, “Have you ever been disciplined for violating a company policy?” And consider getting the candidate’s permission to run a pre-employment background check. If something turns up, you can address it at that time if it’s relevant, but not during the interview.

21. Do you have a green card?

Similar EEOC prohibited questions are ones that ask about US residency, cultural status or ethnic background, like “Were your parents born here?” or “What’s your ethnicity?” These types of questions can land you in legal trouble.

Instead ask: Are you authorized to work in the US? (this will allow you to determine if you would need to sponsor the job applicant). Or, what languages do you speak or write fluently?

22. Your name is unusual, where are you from?

You can be genuinely curious about someone’s ethnic background, and the question seems innocent enough. But like the question above, you cannot ask this during the interview because it can subconsciously impact your hiring decision if they reveal an ethnic background and feel that you violated EEOC rules by discriminating based on their religion or ethnic heritage.

23. I see you have a tag on your car. Do you have a disability or work restriction?

This question can suggest discrimination based on a perceived physicality. The Americans with Disabilities Act (ADA) protects people with disabilities from discrimination as long as they can perform a job with reasonable accommodation.

Instead ask: Can you stand for 7 hours per day? Or, are you able to to lift 25 lbs on a regular basis? (In other words, keep your questions related to the specific job requirements of the position.)

24. Are you pregnant?

This question violates the EEOC’s Pregnancy Discrimination Act (PDA), and you’ll likely get sued if an employee feels she’s been discriminated against by not being offered a job based on her pregnancy. Even an innocent query like, ‘when are you due’? is problematic. Unless the candidate mentions her condition, don’t ask. If you end up hiring her, and it turns out she was pregnant, that’s the time you can talk about your maternity leave policy.

25. I see you’re wearing an engagement ring? Are you getting married soon?

Even an innocent conversation starter like “when’s the big day” that would be perfectly appropriate in a social setting can get you into hot water by bordering on marital status discrimination prohibited by the EEOC. So don’t ask it during an interview for risk of violating labor laws and being slapped with a discrimination lawsuit.

John Crossman - Illegal Interview Questions

Bonus – WORST Question from a Job Candidate

John Crossman, President, Crossman & Company

Of course, interviewers aren’t the only ones who sometimes ask awful questions. Here’s one from a contributor on the flip side.

Once a potential employee asked me, “Why don’t you just make me president of your company?”

We did not ask him in for a second interview.

Bottom Line on Worst Interview Questions

The point of this article is to help you find the best job candidates and stay out of trouble by avoiding ineffective and illegal interview questions. If you’re wondering what you should ask, here’s a list of the best questions to ask. We also provide 11 sample interview evaluation scorecards to help you stay on track.

And if you need help finding good candidates to interview, we recommend posting jobs on Indeed, the #1 job search site. Click the link below to get $50 in job ads to boost your free postings with Indeed.