The “Friendly” Interview: Tricky Questions from Potential Employers

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Recently a friend emailed me a questionnaire she had to complete for a job application. She wanted light editing on her answers before she sent them off, but immediately I noticed a big problem: although the questionnaire was for a professional position, her answers were not professional. I don’t mean that she wrote terrible answers, but most of her answers in no way related to the job. Instead, they read like a conversation you might have on a first date. Here’s an example of what I mean:

Question: Tell us a little about yourself. We want to get to know you. 🙂

Answer: I live in [town name] with my boyfriend, [boyfriend’s name], and enjoy taking long walks in the countryside. I’ve always wanted to be a professional writer, even before I really knew what that meant. I’m an avid reader, although I watch a lot of Netflix, too, mostly period dramas unless I’m watching gardening shows with [boyfriend’s name].

The answer does what the question asked, it describes my friend and lets you get to know her, but what does it tell you about my friend’s previous work experience or the skills she brings to the job? Nothing.

And that’s not really her fault. The question doesn’t read like an interview question at all. It sounds like a friendly bid to get to know you, and that’s even what the directions for the questionnaire say, that the company wants to know you as a person. Many companies today, especially those courting Millenial workers, have taken this more conversational tack in order to seem less like faceless corporations and more like people-focused, innovative “callings”.

The problem is, they are still businesses. They still want employees with skill sets that meet their needs and experience that lends itself to the job. And despite the innumerable changes taking place in today’s work world, the interview is still the primary tool used to evaluate potential employees. As Rachel Premack and Jacquelyn Smith explain in their article “21 Job Interview Questions that are Designed to Trick You,” “Savvy hiring managers can glean a ton of information about you by asking just a few, well-chosen questions. But while they may seem simple, some are actually designed to get you to reveal information you may have been trying to conceal. In other words: they’re trick questions.” While this may feel underhanded or like interviewers are setting you up to fail, this interview strategy helps them determine whether workers have the soft skills that are becoming increasingly important in the workforce.

Getting to Know You…as an Employee

So how should my friend have answered these questions? This is the advice I gave her:

These questions are not just about getting to know you, but about getting to know you as an employee. What they really want to know is how you actually behave in the workplace, not just how you think you behave. Your answers should all reveal something about you as a worker. They should give an impression of what it would be like to work with you.

Or as James Ball, in his article “11 Tricky Personality Interview Questions and How NOT to Answer Them!”, reminds readers, “Your interviewer will use personality questions like the ones we’ve outlined below to assess…how well you’ll fit in with the team and culture, whether you’re going to be a pain to manage, [and] what motivates you.” It’s important that your answers are honest and reflect who you really are, but at the same time you need to think about the questions from the perspective of the employer — what information are they really trying to get?

When my friend began thinking of the question in this light, she decided to revise her answer to focus on her experience within in her career field:

I have worked as an editor for [company name] for two years, having quickly advanced from a content writer position. My job requires me to edit the educational materials our tutors produce, ensure alignment of the product across multiple media, and revise for clarity and correctness.

In addition to my full-time job, I have worked as a freelance writer for four years. My writing experience is vast, having covered everything from blog posts for cooks and tailors to ad copy for large corporate chains. I began my freelance business because, while I enjoy the challenges of being an editor, my passion lies in the actual writing…

…In my spare time, I’m a member of a local writing group, [group name], where I workshop my short stories. I find the freedom of writing fiction helps me bring more creativity to my professional writing…

She begins by talking about the information that is most meaningful to her audience — her relevant work experience. From there, she moves to hobbies that are somewhat related to her career and she explains why those hobbies are relevant to this interview. It’s as though she took the “work” slice of her life and gave to the interviewer, pulling out the related information that would help the employer see why she would be a good fit for the position. Importantly, this is an opportunity for her to talk about the kinds of things that would not make it onto a resumé, but might still help to show how passionate she is about her line of work.

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Taking Calculated Risks

Let’s take a look at another classic example of a tricky interview question.

Question: Share an embarrassing moment with us.

My friend chose to write about a time the fire alarm went off at work and she nearly fell in the toilet.

Thankfully no one witnessed this happening, but recently at work I was in the bathroom and learned that the fire alarm is right above the stall! The fire alarm sounded and I almost fell off the toilet with fright! Then I had to make my way outside and pretend that I almost didn’t have a figurative heart attack in the bathroom!

Certainly, that’s an embarrassing and relatable situation. She did what she was asked by the company and wrote about an embarrassing moment. But does this answer make you want to hire her? Probably not.

This question isn’t really about an embarrassing moment; it’s actually about how you deal with strong, negative emotions like embarrassment (or fear, or rejection, etc.). Do you give up and hide? Do you recover? How easily do you get rattled? When things go badly, REALLY badly, how do you cope? This is what the company really wants to know.

So how can you use your answer to this question to demonstrate what you bring to the table?

Here’s another possible reply. If you were an employer reading both of these answers, which one would you respond to more positively?

Years ago I worked as an intern at a diabetic clinic during graduate school. My job was to download the meters and pumps for patients into specified computer software and print out the results to place in the charts for the doctor. Usually, patients took their meters out of the cases, but on this particular day, I’d been handed a full case. Cases contained the meter or pump, test strips, and lancets, which were usually retracted. I did not realize the lancet was open and, as I was trying to wrestle the meter free of its casing, I pricked my finger on the exposed end. Although it didn’t puncture the skin, I was aware that if this situation ever happened, I had to report it and follow correct protocol.

I felt enormously embarrassed that I’d made such an amateur mistake. The patient had to endure additional blood tests on my account to check for diseases communicable through blood. Even more embarrassing, I absolutely hate having my blood drawn and am prone to passing out. I did not want to pass out in front of my coworkers who dealt with blood every day!

However, I knew the protocol and understood that it was important for everyone’s safety that I follow proper procedures. Thankfully, the patient and I were both ok, and in the end I felt good about doing the right thing. I didn’t have to worry about whether I had contracted something or not, and I was much more careful with the lancets in future. In fact, I included a warning about checking that lancets were retracted when I revised the handbook for future interns.

This second answer is stronger for a number of reasons. First, this embarrassing moment actually relates to the writer’s job performance instead of an accident that could happen anywhere. This is a smart move since this question is being asked in the context of a job interview. Second, this is a much more specific example of an embarrassing moment, and it’s a moment with high stakes. How the writer responds to this situation has very real implications for the safety of the writer and her coworkers. The writer has something to gain from breaking protocol; if she hides her mistake, she saves face with her coworkers and the patients who need to trust her to handle their materials safely. (However, she does the right thing, which is important.) Next, the writer spins this embarrassing moment, demonstrating her integrity (by telling the truth) and her understanding of the job (she does not just blindly follow the rule, but understands why the rule should be followed). Finally, she turns the embarrassing moment into an opportunity to make her work environment safer (she updates the intern manual to prevent this situation in future). As an employer, this anecdote tells me that the writer will take responsibility even when it is difficult and thinks about things globally (what’s best for everyone, not just the writer). This is the kind of employee that would benefit any team.

Showing Growth and Self-Awareness

Here’s another example of a difficult question to answer:

When was a time you handled something poorly at work?

This is a question no one ever wants to answer. It feels like a trap. How can you admit to making a mistake without giving the interviewer a reason to not hire you? My friend decided to be clever and skirt the question:

Early in my career, I made a major error in a piece. I had checked it, my editor checked it, yet this factual mistake remained. Instead of getting angry or blaming someone else, I learned early on not to make excuses, to take ownership of mistakes, acknowledge them, apologize, and learn from them. I take pride in producing high-quality products quickly. Now I proofread much more carefully.

While this might seem like a smart course of action, it could suggest to the interviewer that you’re that you refuse to own up to your mistakes, or that you’re inflexible and unwilling to try things that make you uncomfortable. A better strategy is to show growth or a substantive change in yourself from the moment of the mistake to the present. An answer that sounds like a non-answer can come across as somewhat dishonest in the sense that it omits the information the interviewer really wants.

Exposing a moment she found truly humiliating was difficult, but it allowed her to explain why she had made a big change in her career that ultimately brought her to this interview:

Usually, I pride myself on my people skills. In fact, my coworkers frequently remark how unflappable I am even when dealing with confrontation. However, years ago I had a moment where I definitely lost my cool.

I was teaching a college composition class and had explained over and over that students must give credit to their sources. We spent multiple class meetings covering the topic, and I created a PowerPoint and a handout as an aid for the students. But when the students submitted their essays, most of them had not cited their sources. In a moment of frustration and poor judgment, I sent out a mass email to my students scolding them, concluding with my telling them this was not “rocket science.”

A student in the class made a complaint to my supervisor about my rude behavior, and standard policy was that instructors had to meet with their supervisor to address any complaints. I tried to take ownership of the mistake, but I could hardly explain it to myself.

After much soul searching, I finally admitted that I was very unhappy in the job. My favorite part of my work there was creating the educational materials, but I did not enjoy the time in the classroom or the endless amounts of grading. As soon as I realized that, I began searching for a job that would be a better fit for me. I knew I wanted something that would allow me to research, write, and edit, and it would be nice to capitalize on my experience in higher education. That was how I found my current position editing learning materials, and why I was drawn to this position with your company…

My friend went on to explain the criteria she looked for in a job and how the position she was interviewing for met those criteria. This created a space for her to write about how well this new career suited her and what she finds fulfilling about her work now. Since her answer could suggest she is impulsive and prone to tantrums, she began her answer with an anecdote that shows how out-of-character this moment was for her, and she concluded her answer by reinforcing how her people skills would benefit her in the position she was applying for.

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The Upshot:

Answering tricky interview questions can be stressful. It’s impossible to know exactly how someone will interpret your answers, and even if your answers are incredible, you may still not be the best fit for the job. However, understanding the purpose behind these types of questions and what employers are looking for in your answers gives you a definite edge over the competition.

  • Keep your answers focused on the job you’re applying for. How does your answer relate to that specific position?
  • Consider the question from the interviewer’s perspective. What are they really asking?
  • Be honest and answer the questions you are asked, but emphasize the positive.

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