Toughest Interview Questions to Find out More about your Candidates by Mile Živković on Dec 31, 2018

Interviews are one of the most important parts of the hiring process and often one of the most stressful for the candidates. They often make the decision on whether to accept an offer largely on the interview experience, so it’s important to get it right.

Primarily, this means paying attention to the questions you ask. If you want to find out more about the candidates, there’s only one way to go about it – asking some tough questions.

Why would you ask tough interview questions?

If your guess is – to be mean, you’re absolutely wrong. Tough is completely subjective, and what is tough will depend on the situation, candidate, job position, as well as the candidate themselves. Tough questions are challenging for the candidates and they have several purposes.

First, you’ll asses how the candidates see their own weaknesses and whether they’re even able to recognize them. Second, you’ll find out the way candidates look at a certain task. Finally, you’ll learn more about the ways the candidate communicates with other people at work – superiors, colleagues and subordinates.

Tough interview questions are meant to test the way the candidate thinks and behaves themselves in a workplace setting. They’re not an excuse to ask provocative and inappropriate questions. After all, the interview process is meant to be pleasant for the candidate, so that they get a positive outlook on your employer brand and actually want to come and work for you.

Toughest interview questions

So, what does tough actually mean? Here are some great questions to ask to your candidates to find out how they think and behave in certain situations in the workplace.

  • How do you deal with co-workers who are older and more experienced in this industry but aren’t as educated as you? In today’s workplace, experience and knowing how to do the job often trump education. You’ll find out how the candidate deals with those who are higher up on the ladder but not as educated as them.
  • What’s a time you failed and how did you deal with the aftermath? Everyone makes mistakes, it’s how you deal with them that makes a difference between a great and good employee. An honest answer to this question will tell you lots about the candidate – from the way they work, to how they manage errors and what their soft skills are like.
  • What are your greatest weaknesses? Admittedly, most HR experts state that the answers to this question are usually similar, along the lines of I’m a perfectionist. An honest answer will let you take a glance at how self-critical the candidate is about their work.
  • What’s a time that you stood up to someone to do the right thing? Sometimes, you have to defend your coworkers for things they’ve done (or not). Standing up for others in the workplace is an admirable quality you’d want in your next hire.
  • Why aren’t you working at a particular job anymore? This can be a sensitive topic, but it’s a good way to find out if the candidate left their previous role on good terms or as a result of some incident.
  • What did you like/dislike about your last job (or a particular job from the past)?Learn what the candidate finds appealing in a position and what puts them off (and makes them leave). If they valued independence in their last job and your position has a focus on teamwork, they’re probably not a good fit.
  • Tell me about the time when you made an error in judgement. Find out whether the candidate owns up to their mistakes and what they do to make things right.
  • What are you currently reading? You’ll learn what the candidate is reading to improve themselves professionally (or for leisure), be it books, blogs, whitepapers, comic books or whatever else comes to mind.
  • How do you imagine your first 30/90/xx days at the company? If they’ve done some research about the company and what the job entails, they should have some idea of what they’ll be able to do within a certain time frame. Of course, they’ll only be able to answer this if your job description is on point and you’ve given them plenty of information in the interview itself.

Take a look at the screenshot below for an idea on how Toptal takes care of this, for each of their numerous positions:

toptal job ad
  • How do you imagine your ideal day working as an XXX position? If they don’t have enough information about the position, don’t expect any miracles here. However, if they know the position well enough, they’ll be able to tell what they imagine as their perfect day at work.
  • Why should we hire you? Another version of the famous “Sell me this pen“, this is a unique opportunity for the candidate to sell themselves and convince you they’re the best person for the job – which is especially important if it’s a position where they’ have to convince others (clients, upper management) to have faith in their ideas.
  • What did your former boss most often criticize about you? The candidate should ideally give an honest answer about their biggest faults at work, as noted by previous employers.
  • How do you handle stressful situations? Stress is never a good thing, and some position (such as sales, upper management) carry a lot of it. If a candidate can’t handle stress, they probably won’t function well in a high-paced environment.
  • Tell me about your most negative/positive management experience. If the candidate has had poor experience with management, you can (attempt to) see whether the candidate was at fault or the employer. Likewise, you’ll learn what they appreciate in a manager.
  • Why do you want to work at our company? Distinguish whether the candidate merely wants to work for a paycheck or they have some intrinsic motivation to work for your company in specific.
    • Why do you want to work at this particular job position? Besides ticking all the boxes, what makes the candidate want to work as a marketing manager or a data scientist, for example?
  • How would you describe your current employer? Speaking poorly about previous employers is generally bad taste – this is a great place to show off good manners.
  • What do you think, which words would your current colleagues/employer use to describe you? Get an idea of how self-critical and aware the candidate is about the opinions of their coworkers and managers.
  • Who was your best/worst boss and why? Everyone has their fair share of good and bad experience with employers. With this question, you’ll find out the candidate’s preferred style of management and leadership and what they found good and bad about their previous bosses.
  • If a colleague who is sitting at the desk next to you had an annoying habit, how would you resolve it? Working in an office is not always sunshine and roses and sometimes conflicts arise. You want to make sure the candidate can resolve them in a civilized manner.
  • What do you expect from a supervisor/subordinate? Some candidates prefer to be pampered at work, others require independence to function at their own place. You’ll get a good idea of the requirements the candidate has from their managers and subordinates.
  • Describe your ideal work environment (being it the office place, how it looks, colleagues, approach to work, etc.). What’s their ideal workplace like? If they expect isolation and silence and you’re working in an open space with 50 people, it’s hardly a match made in heaven.
  • What is a one thing you are most proud of professionally? Find out their biggest professional achievement, be it a reward, certification, promotion, a project – their personal masterpiece that shows them in best light to you as prospective employer.
  • Do you work better alone or in a team and what makes it so? Depending on the position, you could be looking for a team player or someone who works better solo.
  • Do you have any questions for us? Perhaps the toughest question of them all – what’s the one thing you haven’t said but the candidate wants to know? This is another excellent way to find out who’s done their research and really wants the job.

When these questions aren’t enough…

You may want to find out more, if a question is especially interesting for a given position or the candidate, you can simply ask sub-questions to your heart’s content. Alternatively, try out an interrogation technique called the 5 Whys. By asking why for 5 times, in theory, you’ll establish a cause and effect relationship and learn more about the candidate being interviewed. For example…

Candidate: I decided to leave my previous job myself, I wasn’t let go.

  1. Why: I didn’t feel motivated to work
  2. Why: It didn’t align with my career goals.
  3. Why: I was doing the same job for years.
  4. Why: Our team wasn’t growing and there was no room for promotion.
  5. Why: The ROI wasn’t enough to justify hiring more people for the team.

Ideally, you’ll be at the bottom of it at the 5th why, but it could take more questions and time. You’re only limited by time and the candidate’s will for cooperation.

In the end

As we’ve mentioned, the aim of these questions is to find out more about the candidate, their experience, personality and how they behave at work – not to put them in an unpleasant situation. This is by no means the ultimate, most comprehensive list of toughest interview questions. If you have some of your own, please write them down in the comments below!

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