Cool (and not-so cool) Job Interview Questions

The questions asked during a job interview, or even as a pre-screening question during the application process, depend in large part on the role itself. You wouldn't ask someone applying for a nursing position how they increased sales at their previous job (well, in the American health care system, you might).

Many of these suggestions below are a bit broader and will work for most positions. The direct answer to the question is valuable on its own, but also pay attention to other aspects of the candidate's answer. Does a particular question solicit an especially strong response? Can you tell they are making a big effort not to say something? Sometimes what isn't said can be more telling than what is expressed.

For the Employer

Think of an example of a challenge you overcame that required seeking the help of others. How did you choose who to ask and what did you do to motivate them to help out?

This one gets the candidate talking about how they approach situations that involve teamwork. Read between the lines and give some thought to what the candidate doesn't say as much as what they do say. Were they reluctant to cooperate? Do you get the impression they are okay working in a team as long as they get the credit? Are they overly reluctant to seek help from others?

What kind of personality types do you prefer to work with and what types get under your skin the quickest? Give an example of each.

Not everyone gets along with everyone else. That's human nature and is to be expected. This question gives you insight into the personalities the candidate gels with — pay attention to their answer knowing who their teammates will be if hired.

A follow-up question might be, "Provide an example of someone you've worked with in the past that you just couldn't seem to get along with, and how you dealt with it."

For you to be the most productive and engaged in your job, what advice would you give your supervisor?

Few candidates have heard this question during a job interview because most don't think that the way they are managed is flexible. It is a common assumption that the role is led in a particular way and that the employee must adapt to it, never the other way around.

Asking the candidate how they prefer to be managed sheds light on what they think makes them most effective in their role. It also can reveal their own level of maturity and self awareness. Give the candidate a moment to think about this one and encourage them to provide an honest response, especially if you are the person who will be their supervisor if hired.

What job from your work history did you find most satisfactory and why? What job from your work history was the least satisfactory and why?

Encourage the candidate to be introspective, open and honest about their answers. There are no right or wrong responses, as the intention is to understand the drivers of their personal engagement and disengagement.

For the Candidate

The classic advice to job candidates is to ask questions of the prospective employer when given the opportunity during a job interview. Not all questions are purely for your own sake, however.

What you ask can tell the employer a great deal about you as a candidate and can have a big influence on your chances of advancing in the hiring process. Some questions, however, might result in a curt, "Thank you for your time" and being escorted to the door.

Be smart about it. Asking too many questions can quickly feel tiring or tedious to the interviewer, so you must choose your questions wisely. Read the room; it's best to make these questions feel more like a conversation than an interrogation.

Why is this position open?

This matters a great deal to you as a candidate. Be prepared to ask a follow-up question based on the answer given. Don't be surprised if the answer is vague, however, as not all reasons, even if honest, can be disclosed in detail.

This is one of those questions where what isn't said can tell you as much (or more) as what the interviewer is willing to say.

A good follow-up question might, "How long has the position been vacant?"

What does success in this position look like?

This is perhaps the most important question a candidate can ask during an interview. It will convey to the employer that you care about doing a good job and that their answer will make it more likely you'll succeed in that effort.

What if their answer is vague? A good follow-up question might be, "How much input would I have in shaping the nature or objectives of my position?" What if the nature of the role has changed recently? If so, seek clarity on why the role changed.

It is often asked of a candidate, "Where do you see yourself in five years?" Turn this around and ask the interviewer where they see this role — or you as a candidate — progressing in the next three to five years.

Smart employers know that many employees aren't content to stay in the same role during their tenure. Employers will often have a progression plan where that position can get promoted after a certain period of time or once key objectives or experience levels are met. Not all employers have a progression plan for a position, however, and it's best to get this out in the open before accepting the position.

What are the biggest challenges or obstacles that might reduce my likelihood of being successful in this position?

This question has a bit of a dual meaning. It can be taken in a generic way — what are the challenges to the role itself? — or in a personal way — what are the challenges you as an individual would face?

The benefits of asking this question are two-fold: it tells the employer you are interested in exceeding expectations; you might get a sense if the hiring manager is being honest and forthright about you and/or the position, or if they have unreasonable expectations (that you're unlikely to meet).

The insight you glean from the hiring manager's answer to this question along with your previous questions can be very telling. Do you get the impression the employer is honest and realistic? Or are their expectations unreasonable, perhaps indicated by the position experiencing frequent turnover or lying vacant for a long period of time.

What Not to Ask

Finally, here are a few examples of questions that you should never ask, or are potential red flags if they are asked of you.

[From the employer] Why are man-hole covers round?

These type of 'riddle' questions don't convey any actionable insight or knowledge to the employer and often they just make the interviewer feel like they're being clever and smarter than the candidate.

[From the employer] Where do you see yourself in five years?

Most candidates who take the job search seriously will have rehearsed this question and have a prepared answer. Their answer will be tailored to land them the job, not to give you honest information. Don't waste the time to ask, or if you do, don't put too much stock in the candidate's answer.

Variations to these trope-level questions with rehearsed answers are, "Why should we hire you?" and "What sets you apart from the other candidates?"

[From the employer] Are you married? Do you have any kids? Do you plan on having kids? What church do you attend? etc.

Questions such as these are not only irrelevant, they are illegal. Other variations that violate the law include questions about the candidate's voting history or political leanings, thinly veiled hints or overt questions about sexuality or gender or marital status, anything involving religious beliefs (or lack of), and topics that touch on the candidate's age or where they live, etc.

Essentially, if interview questions feel personal or are clearly irrelevant to the position, the candidate not only doesn't have to answer, but probably doesn't want to work at that employer anyway. The person asking the question might be ignorant of the law but that's not a valid excuse nor is it the candidate's responsibility to find out or to correct them.

If you get to the point of having to say anything along the lines of, "My sexuality/gender/marital status/religion/etc. is not relevant, nor is it legal for you to ask me that," then you probably shouldn't be considering working there in the first place. You can also alert your state's labor relations board as the employer will likely be asking similar questions of other candidates who may not be aware it's illegal to do so.

[From the candidate] How much vacation do I get the first year?

Although this is a tangible question that a candidate has a right to know before accepting the position, it's a red flag to ask it during the job interview. It makes the hiring manager think you're not there to do a good job but to reap as many benefits as you can out of the position. In other words, it makes you look selfish, not hirable. Wait until an offer is made, then seek clarification about this and other terms of employment.

And now our final question a candidate should never ask during a job interview:

When can I expect to get my first raise?

No analysis is needed on this one. If you have to ask...