Scary Interview Questions

Updated: Nov 9, 2018

For whatever reason, job interviews are one of those weird situations where we all get nervous and start to act like someone we are not.


So it seems fitting to celebrate Halloween--a fun night for playing dress up and pretending to be a fantasy character--with some of the scariest interview questions my friends and readers shared with me from real interviews in their lives.



These are real questions, asked in real interviews, and in a lot of these cases, these crazy questions were aced because, well, they got the job!


So enjoy a little fun, but please, in the name of all that is hallowed: stop asking these interview questions!


To help you out, I'll give you some alternates.



1. "So, tell me about yourself...."

Ah yes, the perennial snoozer. The classic opener.


Guess what this question tells your interviewee? It tells them you are not prepared. You have no idea what to ask.


Please stop opening interviews with this question. At best, you will get a very strong communicator's elevator speech, but that will be extremely rare. You could get a person's sad life story. You could get a deer-in-headlights stare. You could get a 10-minute spiel on something that is utterly unrelated to your hiring needs.


Usually this question is employed to get a summary of a person's career. That's not a bad idea, and could really give you an insight into their story, their communication style, their motivators, and their strengths. But you should not ask in such general terms.


Try this instead: "In about 3 minutes, can you give me the "Reader's Digest" version of your career story?"

Why this works better: With this question you have given your candidate a time limit (3 min), and asked specifically for a summary of a story. All of these directions are more precise parameters to help you get right to the important information in their career story.


I do not recommend using this question with entry-level candidates or new graduates. This is best used when you have a person with about 8-15 years or more of a career under their belt.


What to look for: listen for motivations in career or geographical moves, common threads despite career changes, and red flags like always blaming others for career problems.



2. What are your salary requirements?

This is a question that understandably strikes fear into the hearts of job candidates everywhere.


Everyone worries that this conversation will happen at the wrong time, or that they will choose the wrong number--too low or too high--and ruin their chances for a great job with great pay.


And really, interviewers are scared by this conversation too. It's always awkward to ask someone about anything related to money. Plus, what if the person you think is great for the job is way out of your league on salary? Will they laugh in your face?


Try this instead: From the perspective of a hiring manager or business owner, the best way to avoid awkwardness is to do solid research on the market for the salary you need to get your ideal candidates. Get buy-in on the budget for your open position from any stakeholders in the company. Then, you can confidently post a salary range for your job and anyone who has reached the interview stage will be aware of the range. Or if you choose not to post the salary, you can at least take time in the interview to discuss it:

"We are looking at a budget of $74,000-$82,000 per year for this position, does that fit with your expectations for your next role?"


Why this works better: money is a great motivator and can be very attractive, but it's not everything. I believe firmly in posting salaries for available jobs whenever possible, and allowing those who are exploring careers at your company to opt in or out of the process early on. Not everyone will opt out, even if it is the same or less than their current salary. Many other factors will weigh in: commute, work/life balance, a better boss, more meaningful work, a different shift, etc.


What to look for: again we are looking for motivators. If they are open to a significant salary cut, ask them why. Ask them pointedly if they will be able to meet their monthly obligations of bills if they make less money. If they are currently making significantly less, explore if they have held the same responsibilities, or have the right skill level you're looking for.




3. Weird psychological questions.

Sometimes, conducting a job interview causes us to think that suddenly we need to become a clinical psychologist, delving into the depths of a personality with unusual questions that reveal their innermost being.


Just stop right there.


Unless you actually are a psychologist, don't try to impersonate one. You are most likely woefully unqualified to interpret answers to these types of questions anyway, resulting in precious interview time wasted in what is essentially a silly parlor game.


Try this instead: "How would your coworkers [fellow students/boss/customers] describe you? Why do you think they would describe you that way?"

While this approach is still technically theoretical, it gets them thinking about how they come across to other important stakeholders in their current job, and allows opportunities for you to ask for examples of their work situations and challenges.


What to look for: their answers may reveal strengths, weaknesses, or blind spots that you can dig into with further questions. Also, if you use reference checks, go ahead and figure out if the answers match up.


4. "Where do you see yourself in five years?"

This is another often-asked, favorite interview question. But it can be scary to candidates, and I understand why. It seems like there are a lot of ways this could go wrong.


I want people to stop asking this question, and it's more than just a pet-peeve.

Today's worker is simply not planning or expecting to stay in a job for 5+ years. That's not exactly a value judgement against the workers at all: increased mobility, questionable global economics, and even just being good at what you're doing and getting recruited away are all reasons not to stay in job for decades like our dads did.


Try this instead: "What skills do you think you have that will make you capable to take on this job on day one?"


The better discussion centers around what an employee could bring to the table NOW and whether that would make all of this effort and investment in hiring someone on worthwhile. And if you want you can follow up with: "What goals do you have, and how do you think this job will lead you to achieving those goals?"


What to look for: does this person's current skills line up with the job? Will they be able to hit the ground running, or take months to train? Do their long-term goals seem like a potential fit for your company in some way? Or are they just biding time until a completely different career comes along? Is that a problem, or are you ok with that?




5. "What are your weaknesses?"

Ah, the invitation to humble brag. It's a classic!


The problem with this question and it's sister, "What are your strengths?" is that they throw subtlety to the wind. I'm all for direct questions, but this starts to get weird.


Also, since when are you relying upon your candidate to summarize the interview for you? If you are prepared, you should be asking pointed questions about their knowledge, skills and experience, and then deducing their strengths and weaknesses yourself.


Try this instead: "How would you rate your skills in [job requirement], on a scale of 1-10? Why did you give yourself that score?"


This approach works well as part of a structured interview focused on the knowledge, skills, and abilities needed for a job. It again forces the candidate to provide some evidence of their work experiences.


What to look for: weaknesses and strengths. Most people will try to be honest with you (not everyone of course) and will most likely underrate their skills. You can dig deeper and ask more questions on a certain skill set to gather more details too. And finally, if you do reference checks, you can try to confirm their answers as well.



Happy Halloween everyone! And happy interviewing!


Get my Guide to Interviewing Like a Boss to learn more about upping your interview game.



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