15 Tough Interview Questions Candidates Won’t Expect

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15 Tough Interview Questions Candidates Won’t Expect

As professional recruiters, we know that we have to go beyond run-of-the-mill interviews and draft some tough interview questions to challenge the candidates when we want to hire talent. We are not talking about those weird – how many pianos are there in New York – types of questions, although we will share some in the future. This guide will focus on tough interview questions and answers we expect from the candidates to give us in-depth insight into their soft skills, attitudes, behavior, critical thinking, self-awareness, and more. You should design such an interview not intending to catch applicants off-guard and put them in awkward situations. We are doing this to know them better after we put them through all the pre-employment assessment tests relevant to the job role.

Why Do We Need to Ask Candidates Tough Interview Questions?

Before we begin, it is important to realize that these questions and their answers impact employees’ job satisfaction levels and employee turnover. In the past years, Google and other corporate giants became famous for their tricky interview questions. Beyond finding people with outstanding critical and creative thinking skills, we first want to find an organizational culture fit. Google does not do this out of sheer whim. Studies showed the following:

A 10% more difficult job interview process correlates with 2.6% higher employee satisfaction later on;

On a five-point scale (with 1 = very easy and 5 = very difficult), the optimal or “best” interview difficulty that leads to the highest employee satisfaction is 4 out of 5;

This 4-level difficulty translates into an interview experience that is difficult but not overwhelmingly so for candidates.

It is not news for anyone that employee satisfaction has a positive link to employee retention and growth. In other words, answering tough interview questions is good for both the organization and the candidates.

Keep in mind that most experienced job applicants will expect a few or many of the following tough interview questions. Some of them will come prepared with rehearsed answers. For this reason, we never rely solely on interviews with standard or behavioral questions. After using personality assessments, cognitive tests, and other aptitude evaluations, we can draft a set of tough interview questions to challenge the candidates.

What Do We Expect to Learn from These Tricky Interview Questions?

Google does not expect job applicants to reveal the exact number of pianos in the city of New York. They want to learn how candidates think and reason to reach an approximate number. In the same vein, the following questions in this guide help you understand better some or more of the following candidates’ skills, aptitudes, behaviors, integrity levels, etc.:

  • Self-awareness and willingness to improve;
  • Levels of honesty, adaptability & flexibility in a new working environment (organizational culture);
  • Attitudes towards authority;
  • Attitudes regarding cooperation, collaboration, and teamwork;
  • Problem-solving, decision-making, creative thinking;
  • Personality traits.

To get more inspiration for your tricky interview questions, we recommend using our guide on manager interview questions and our guide on leadership assessment tools.  

15 Tough Interview Questions to Ask Candidates to Challenge Them

tricky interview questions

For clarity, we will break down the questions depending on their main characteristics and purposes.

I. The Strengths & Weaknesses Tricky Interview Questions

Both candidates and we are used to such weaknesses-related questions, but we have to ask them, and they should give us enough answers so we can gather as much information about them as we can.

1. What is your greatest weakness?

We don’t want candidates to humblebrag, nor give us canned answers along the lines of “I don’t have any” or start sharing their dark past. This question tries to find if a candidate is self-aware and honest about areas where they need improvement. We care about this because we engage employees in growth programs. From better time management to improved delegating skills, we want to learn what our candidates ace and where they admit they need “upgrades.”

2. Tell me about a mistake you made at a past job and what you learned from it

Candidates are people and make mistakes, no matter how proficient they are at their jobs. We ask this question to gauge applicants’ flexibility and willingness to admit their own mistakes and learn from them. After all, self-improvement is a core value for many organizations.

3. Why should we hire you? What do you think you have that other candidates don’t?

You probably know why you want to hire that person. They probably passed all your cognitive skills assessments and personality inventories with flying colors. However, you want to learn how candidates position themselves in comparison to the competition. Allow them to market themselves. Answers such as “I am the best” or “I am a good employee because I do everything my manager says” are not ideal, however. The candidate should correlate skills, strengths, and personality traits to your corporate culture’s job requirements.

4. What do most of your coworkers often criticize about you? How about your friends?

When it comes to coming prepared for tough interview questions, this is what we were discussing. This tricky question, while not expected, encourages candidates to turn weaknesses into strengths.

“I am too perfectionist” or “I invest so much into my projects, I often consider my work not to be good enough” are good answers on paper. But what do they mean? How does the candidate define “perfectionism” or “investing too much into the work?”

With this question, you can find plenty of an applicant’s appetite for honesty, integrity, etc. It can also reveal rehearsed answers and presence of mind to knowledge some weak points without self-deprecating or, on the contrary, humblebragging.

An answer along the lines of “I cannot be productive early in the morning, but I do my best work in the afternoon as the numbers I showed you demonstrate” opens an entire area to explore. You have the chance to analyze the interviewee’s skills and position towards time management, prioritization, teamwork, flexible working hours, overtime, work from home, and other aspects we care about when adding new employees to a team.

5. Do you consider yourself a lucky person?

Such question gauges candidates’ perceived levels of optimism, pessimism, and realism. Moreover, it gives you a sense of what potential employees see as “luck.” Is it a combination of identifying big or subtle opportunities, hard work, dedication, etc., or something else? This tricky question, in particular, can lead to some interesting personality/behavior revelations, so note down the answers carefully.

II. Behavioral Difficult Interview Questions

As you very well know, behavioral interview questions elicit candidates to offer you real-life (and sometimes hypothetical) examples and narratives. You have a load of behavioral interview questions to ask that tap into interpersonal skills, integrity, conflict resolution and management, and more. Nevertheless, even if some seasoned candidates will know what to expect and even use the STAR method to answer, here are some tricky questions to ask to provoke them to open up to you:

1. Tell me about a situation where you needed the motivation to do your job/accomplish work goals. What were the factors that “convinced” you to keep up with your work?

Allow the candidate to talk about motivating factors, how they handle stress, lack of engagement, receiving feedback, intrinsic or extrinsic motivation, locus of control, and more. You are not a clinician, so you shouldn’t get into complex psychological evaluations. However, there is a huge difference between “I saw my project’s numbers, and they motivated me to do an even better job next month” and “I know if I don’t do my job, my boss will fire me.”

2. If we would offer you a management position instead of the one you are currently applying to, what would you say and why?

Now, isn’t this a trick interview question? Would the candidate accept the job, thankfully? Would they refuse it politely? What are their arguments for any of the two decisions? Among all the tough interview questions to ask candidates, this one might challenge them to solve a problem, make a decision, reason an argument, think creatively and offer a clear response.

3. Are you willing to have failures at this job and, if they happen, how would you manage them?

Nobody wants to fail at their job on purpose, but it happens. With this question, you want to learn how candidates respond to failure, manage errors and disappointments, and what they are willing to learn from the entire experience.

4. One of your colleagues is always late in answering your emails or requests. What do you do?

You can test teamwork skills and conflict management abilities in many ways. There is no such thing as perfection, so issues arise every day in a working environment. You want to learn about the small daily nuisances and their resolution. Of course, you can ask about serious, life-or-death conflicts and struggles, but they rarely occur in well-organized teams and companies. On the other hand, we all have coworkers who sometimes get on our nerves one way or another. The key is how we deal with such situations and people.

5. If you could turn back time by ten years, what would you change about your life/job?

We all dream about time travel to the past to correct some mistakes or make other choices. Maybe your candidates do too. It is one of the trickiest questions to ask in an interview, as they trigger a lot of emotions and plenty of answers that can surprise you.

III. Job, Life, and Experience Tough Interview Questions

The next batch of questions isn’t mandatory, but it would help if you asked them. They address more subtle personality traits, attitudes, behaviors, and opinions. Again, you are not there to make a diagnosis, but you can note some red flags in case any appear.

1. Are there any tasks/duties you wouldn’t accept to accomplish?

If your company wrote a professional job description, your candidate understands well what tasks the job entails. However, this discussion is about boundaries, weaknesses, and attitudes that you might not learn about through other means.

2. What did you like most and disliked most about your previous job?

It is a trick question because it can allow you to understand whether a candidate is a complainer. Listen to what they say, as it can help you formulate an employee growth path. On the contrary, the answers and their tone might raise some flags regarding the candidates’ motivation, behaviors, coping mechanisms, responsibility, and much more.

3. Who was your best manager/supervisor, and who was the worst – and why?

Smart candidates will instinctively navigate the answer to this question to avoid badmouthing former managers. Nevertheless, you should insist on the “who” and the “why.” Here, the answers can reveal leadership skills, styles, and traits your candidates appreciate. You can also learn more about how applicants respond to authority, engage in relationships with superiors, manage potential conflicts, and so on.

4. What did you want to be when you grew up? How far are you from that dream?

Among all the tough interview questions that can challenge your candidates, this is one of the trickiest. Most children want to become doctors, astronauts, or lawyers. If your candidate applied for a marketing specialist position, you want to know more about the chosen educational and career paths. The decision-making process, expectations vs. reality, motivation, and life stories give a rich foundation for a revelatory conversation.

5. What are your expectations for this job?

It is more than just salary, and everybody knows this. Encouraging the candidates to ask questions about salary, benefits, and rewards is great. Nevertheless, please encourage them to express their views and expectations regarding this job. You will get very surprising answers to this question.

Bottom Line

We hope you enjoyed our selection of tough interview questions for candidates to challenge them and learn more about them. We are sure you used it even more in your current practice. If you have more examples to get our inspiration going, feel free to share them with the recruitment community!

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