Five Insulting Job Interview Questions (And How To Ask Better Ones)

Earlier this year, I embarked a slightly scary journey down a path I haven’t been down in a long time: I started looking for a new job. I had a conversation with my current employer, and I got the approval to look for a job while I still kept my existing job. I then set out on an application spree: I updated my resume, applied to dozens of job openings, talked to several potential employers via email and on the phone, and landed a few in-person interviews.

It’s funny: I haven’t been in honest-to-goodness “job search mode” since 2010, which is almost eight years ago, and it’s very interesting to see how the process has changed since then… and how it hasn’t.

The biggest thing I’ve noticed that’s new and different is an innovative new type of web application that has inserted itself like an unwanted virus in almost every company’s hiring process: an Applicant Tracking System, or ATS.

Apparently, everyone who’s searched for a job recently already knows what these are. But I sure felt like an old fuddy-duddy trying to figure out what an ATS is, and I’m still marveling at how awkward, unhelpful, and discouraging they are. If you haven’t seen one before, an ATS is godawful, miserable thing that’s essentially an online version of the life-sucking torture device used on Wesley in the Princess Bride. When you apply for a job using an ATS system, you painstakingly fill out all the required information, then furtively press the submit button to apply for the job. After you do, a message pops up saying: “I’ve just sucked one year of your life away. How do you feel?”

Aside from this so-called innovation (which I’m almost sure just allows companies to discriminate in new ways that are much harder to perceive), there is one big thing I’ve noticed about the hiring process that hasn’t changed: the interview questions. They’re quite shocking.

Not the questions you’d expect, of course, like: “What’s your background?” or “Can you tell us about yourself?” Those are fine, helpful questions and they’re good conversation starters. No, the questions that I’ve been surprised by are the same bad questions people asked me in my earlier days that I thought we’d have gotten over by now. You know the ones: the questions that insult you by the very way they’re phrased. Questions like “How motivated are you by money?” or “Can you sell me this pen?” or “If money were no object, what would your ideal job be?”

As I said, I’ve been out of practice, having not needed to interview for a job that I really wanted for almost eight years. (I haven’t worked the same job in that time—I’ve just had a few different jobs come my way quite easily without needing to apply). But it really makes me feel like companies are going about this the wrong way: if you think about it, the hiring process is really very similar to the dating scene that hopeful young singles survive each day as they try to find the love of their lives. Except that in dating, men and women try to treat each other as equals, and the object of the game isn’t to make the other person feel like a miserable failure.

It’s strange: in the business dating game, everybody lies to each other, they ask questions that they know won’t get honest answers, everybody is paranoid that the other party might accidentally get the upper hand, and all that matters is that you don’t get caught cheating. What kind of game is that? I have nothing clever to say about this: it’s just… a really, really bad game.

As with most things in life, I can sympathize with both sides: I’ve been a job seeker, and I’ve been a hiring manager as well. In the mid-2000s, I was the first point of contact for all of my employer’s hiring efforts. I’ve sifted through hundreds—perhaps thousands—of resumes, applications, and emails from hopeful job seekers. I’ve also performed phone screenings, in-person interviews, follow-up interviews, and I’ve even had the (dis)pleasure of being the one to make the dreaded phone calls telling applicants that “We’ve decided not to hire you, but I wish you the best of luck in your job search.” Working as a hiring manager, my rule number one was: “Treat everyone with dignity, especially the people I reject.”

So here I am, applying for jobs myself, and forgetting that many people view the job process from a different perspective. It seems many employers view the hiring process as a zero-sum game: if they win, you must lose. But this is utter nonsense. Think about it: if you’re a hiring manager with an open position, job applicants will literally line up by the dozen to come into your office and sit as a willing victim while you pummel them with a barrage of questions that suit your fancy, no matter how unflattering. Why do they put up with this? Because they want to work for you. This alone, in my mind, is reason enough to treat them with respect.

We’re all adults here: we have to realize that both people in the room want the same end result. The worker wants a job with the employer, and the employer wants a worker for the job. It’s a win-win situation. You’re not enemies during the interview—you’re trying to see if you can help each other out. At a base level, it really is that simple.

I’ve blogged before about the first step in the job seeking process: preparing your resume. As I said, I’ve gotten paper cuts from the number of paper resumes I’ve processed. But here I am, bewildered at the questions people are asking. Perhaps I can shed some light on my perspective on the hiring process from the interviewing angle as well. I really want to be a force for helpful feedback not only to the job seekers, but to the hiring managers as well. Here’s my take on “both sides of the table” during an interview.

Five Insulting Interview Questions You Should Stop Asking


Question #1: “What’s your biggest weakness?”

Why it’s insulting: This interview question has three serious weaknesses (no pun intended).

First, there’s no truly good answer for it. Note: some clever people will advise you to “turn this question into a conversation about your strengths.” This is good advice, but that doesn’t mean the question is any good. It isn’t. It’s an awful question.

Second, you’re asking your applicant to incriminate himself/herself. If you recall, the Constitution of the United States was amended to prevent this in legal situations. Yes, I know the Fifth Amendment doesn’t apply here. But the principle still stands. Let’s go back to the dating game: would you ask your potential spouse the same question? Even if you would, would you ask this on the first date?

Third, it’s very lazy. With this question, you’re asking the applicant to do your job for you. If you’re any good at interviewing people (which is an acquired skill, by the way), you should be able to determine the applicant’s biggest weakness on your own at the end of the interview.

Here’s a better question to ask: “Have you ever made a big or expensive mistake at a previous job? How did you handle that?”

Why it’s better: if you’re really so concerned about your applicant’s flaws (and I’ve never understood this obsession anyway), this approach tries to get at the question behind the question. Aside from the fact that you’re not directly challenging the applicant’s character, it’s also asking about something that’s actually relevant to the workplace. You’re giving them permission to be honest about a failure of theirs, and you’re also giving them an opportunity to show their creative side by wanting to see how they worked to fix a problem they caused.

Question #2: “Where do you see yourself in five years?”

Why it’s insulting: you’re setting up the applicant to insult you with their answer, but you’re asking them not to. Honestly, nobody knows where they will be in five years, where they’ll be living, or if they’ll still be living in five years. Nobody has the capacity to think about the answer in any realistic sense. Your poor applicant will be thinking on their feet, making up the most plausible vanilla answer they can possibly think of and hope it doesn’t hurt them in some way they can’t know.

You’re painting them into a corner with this one. Odds are, if they were honest with you, they’d say something like: “In five years, I’d like to be doing your job.” Or: “In five years, I hope to be working at a better company, since this job is just a stepping stone for me anyway.” Really—how honest do you want them to be?

Here’s a better question to ask: “We’re looking to hire a candidate for this role that stays in this role for the next three years. Is that okay with you?”

Why it’s better: because it’s honest. I know, I know… they could lie to you with their answer here too. But at least in this case, you’re giving them an honest way out. You might discover something. They may tell you “Oh. Hmm… well, I was hoping for something more upwardly mobile that had a faster opportunity for growth.” Bingo! This is a win-win! Even if their answer shows they’re not a good fit for this particular role, that’s what you wanted, right? Yes: that’s the whole purpose of having the interview in the first place. Perhaps you can find a different role in your organization for them, or maybe you can’t. But at least now you know, and there was no pretending needed.

Plus—and this is very important but hiring managers don’t want to hear it—if you’ve created a position in your company that’s so distasteful that you can’t get someone to stay in the role for three years, maybe you’ve done an awful job creating the position in the first place. Maybe you’ve created a role where anyone you hire for it will quit in six months because the job sucks. That’s your fault, not theirs.

Question #3: “What are your salary requirements?”

Why it’s insulting: it’s just another variation on the same theme of “How can I get my applicant to incriminate herself?” In my not-so-humble opinion, a respectable company will post their job salaries, or at least a range salary range. And why not? If the ultimate goal of the interview process is to eliminate false positives and poor candidates as quickly as possible, this should do it. That is, unless your ultimate goal is actually more sinister, and you’re really wanting to string people along so far in the interview process that you get them hooked with a big song and dance of “how great it is working here,” only to drop the bombshell on them that the salary you’re paying is much lower than they expected but they were too polite to ask ahead of time for fear of sounding greedy or presumptuous.

On a separate note, if we’re all aiming for equality of pay (and I strongly support equal pay for equal work), asking this question implies that you’ll pay people differently for the role depending on their own personal circumstances. Employers with this approach are on questionable legal ground here, and they’d do well to simply advertise that the role pays (or starts at) $X/year. This is much better than waiting for someone to tell them how much they need to survive… and then trying to negotiate them down from there (as they often do).

Here’s a better question to ask: none. Why would you even pose this as a question?

Seriously. They’re applying to work for you. You’re the one with the payroll, and the ability to either pay what they want or not. Just tell them what you’re hoping to pay. It’s that simple. Trying to keep job salaries hidden until the last step of the interview is like having a grocery store full of items without price tags—where a customer has to bring their item up to the cash register in order to find out how much it costs. It’s a dirty trick: the only way they can save face is by purchasing the item, even if it’s shockingly expensive.

Question #4: “Why should we hire you?”

Why it’s insulting: do I even need to answer this? This is the big kahuna of the bad interview questions — the one that everyone dreads. This is the question that leaves some people feeling like a mumbling, sputtering idiot, knowing they can do the job you’re hiring for, but can’t necessarily articulate it cleanly during in a neat 15-second sound byte during interrogation.

With this question, you’re asking them to sum up your entire interview in one question. If it’s that simple, why even go through the interview process in the first place? A smart employer would only ask this question and skip all the other steps in the process.

Note: just because some smart people can come up with a clever response to this type of question doesn’t mean it’s a fair question. It’s not fair. The fact that some people may be able to answer this diplomatically is a testament to their abilities — not yours. There are so many problems with the whole reasoning behind this line of inquiry. Think back on your childhood. Was your mom a good mother? Yes? Could she sum up all the ways she was a qualified and worthy mother in thirty seconds under pressure? Of course not. But I’ll bet she did a fine job, just like mine did.

I think by now we’ve proven that test scores aren’t indicative of educational quality in the school system, and I’d encourage employers to remember that interviews aren’t indicative of good employees. Are you hiring people to be professional interviewers? Or are you hiring them to fill a role you have an opening for? Does the job you’re hiring for have “interviewing” as part of the job description?

Here’s a better question to ask (if you absolutely insist on negative questions, which, again, I discourage): “What are some reasons you think you’re a good fit for this role?” or perhaps “Is there anything in the list of tasks or requirements you’re not sure you can do?”

Why they’re better: they’re only slightly different, but they don’t call into question the very character of the applicant. Plus, a truly gifted person could answer this one and even be honest about it. There are so many good responses to this question: if you give people permission to be real and honest, you may be surprised at how they give you answers that actually accomplish your objective, which is to decide whether they’re a good fit or not.

Question #5: “Why do you want to work here?”

Why it’s insulting: are you really going to make the applicant sell you on your own company’s reasons for working there? Why do you keep making your applicants do your job for you? Most job applicants are likely going to be thinking: “Oh crap, I can’t remember—is this the company that had the fitness reimbursement program? That was attractive to me… oh wait, are they the ones that had the generous 401k? I can’t remember!

There are just too many job descriptions that your applicant has been through to remember all the reasons for why they want to work for you. Really, you should be flattered that they’re even interviewing with you. That alone proves that they want to work for you. Why make them grovel? They’re sitting in an interview where they have no power—you hold all the power, not only to give them the job, but also to change their future. That’s as naked and vulnerable as a person can possibly be in a business scenario.

Here’s a better question to ask: “What specific things about our company or this role caught your eye and made you want to apply?”

Why it’s better: man, oh man, is this a better twist on the question! It’s not rude, and it gets down to the real matter at hand. Now, you can sit back and watch their eyes will sparkle and glow as they freely share with you the thing(s) that excited them the most about your organization.

When you ask “Why do you want to work here?”, you’re still in interrogation mode. You’re a bad cop who can (and probably will) use anything they say against them. If you rephrase the question, it puts them at ease, and they may actually share something helpful with you. Plus, you can still use their answer to determine if they’re a good fit for you. But when you say it in a way that questions their sanity, they’re not going to be honest. If you’re just casually asking for someone’s opinion about your product or company… now you’re getting somewhere.

Let’s go back to our dating analogy: is any woman going to ask a man “Why do you want to date me?” Why would she ask that? …and is there any good answer to this question? Isn’t the fact that he wants to date (or even marry) her enough?

Final Thoughts:

If you’re a job seeker and your eyes are glazing over from the sheer number of job postings you’ve been reading, and you’re tired of feeling abused after leaving a job interview… I feel for you. I really do. There’s a light at the end of the tunnel. It’s just a matter of finding the right employer.

If you’re a hiring manager, please just take a moment to treat others as you’d want to be treated yourself. It’s the right thing to do. I’m certain it will give you better hiring results as well. If you believe that the company you work for is worth working for, your organization should be able to stand alone without scare tactics or insulting people who apply. You’re better than that.

Let’s all go forth and contribute to making this a better place to live and work. …and please, for my sake, stop asking insulting questions.

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