30 tough interview questions and answers for successful hiring

Last updated:
February 26, 2021
July 22, 2022
min read
Adrie Smith
Table of contents

Successful hiring requires that you compile tough interview questions and answers you want to ask before the interview process begins. One of the most common reasons for fallouts is a poorly planned recruitment process and reactive hiring.

Preparing appropriate questions is often overlooked, and interviewers rattle through a list of generic questions hoping to hit the target. In the world of successful recruitment, that’s a definite no-no, and you’re setting yourself up for potential failure.

Interviews are a brief opportunity to understand a candidate’s potential as a future employee in your company. Use the time wisely by focusing on core necessities and candidate responses. Remember that candidate potential for one vacancy doesn’t equate the same for another position. Of course, skills are essential, but potential even more so because it embraces cultural, motivational and value fit as well.

Here’s our 30 best tough interview questions and answers

We’ve compiled a list of our top questions that we’ve put in our MidWeekRead (our weekly newsletter).  We’ve compiled a list of top questions that will help you best navigate interview questions weaknesses that stand in the way of successful placements. When selecting from this list, weigh up the relevance to the role, environment and level of responsibility. Also, each question is an opener intended to lead on to further probing questions and hopefully open discussion.

1: What attributes do you look for in a company when applying for a position?

This question is all about extracting info to identify the right fit, so it’s vital to have it on your list. Commonly called the candidate journey, candidates evaluate potential employers carefully before making an employment application. When it comes to employees aligning their values and aspirations with the company culture and opportunities, skills take a backseat. Even if an employee can do the job with their eyes closed, they’ll move on if they’re uncomfortable in their environment or feel that they’re in a dead-end situation.

What you’ll learn: you can see if a candidate’s values and aspirations align with those of the business.

2: What are the three to five expectations that you have of senior leaders in an organization where you’ll work successfully?

Asking a candidate what they expect from management can be an eye-opener. With so much pressure to deliver results, this could be one of those tough interview questions and answers for you to process. Many employees feel unappreciated (and many are), so take note of the answers you get and consider whether you’re living up to existing staff expectations. On the other hand, the candidate’s anticipations might not align with your company.

What you’ll learn: again, you are assessing a candidate’s values and aspirations (and doing a bit of soul-searching).

3: What are your pet peeves?

Still in line with the previous two questions, here you’re looking to see how the candidate will fit in with colleagues as well. Considering that most of us are destined to spend about one-third of our lives at work, we want to be happy there. Hiring someone who’s unhappy has a knock-on effect that negatively influences colleagues and productivity. You know your environment and who the person will be working closely with; listen carefully!

What you’ll learn: what irritates, agitates and infuriates a candidate; if those things exist in your environment move on to the next candidate.

4: Have you ever found an error in your own work? How did it happen, and what did you do about it?

In short – have you ever messed up! You can use this line to test honesty and ego. Anyone who’s been working for a few years has to have made mistakes, big and small. How would they have learnt otherwise? A candidate who claims to have a perfect record is either lying, or they’ve been doing the same mundane, pointless job for years. If you’re hiring for a team position, you don’t have room for egos, and honesty is more desirable than dishonesty.

What you’ll learn: whether a candidate can admit and learn from their mistakes, or if they prefer to shift blame and render themselves blameless.

5: What types of decisions are easiest for you to make and which ones do you find most difficult?

Aligning with the previous question, you want to know if a candidate takes responsibility for the decisions they make. Not every position requires assertiveness, but we can’t altogether avoid making choices in the workplace. No work environment is static, so even if it’s to pick up a call on a colleague’s line, we need to make decisions. Ownership of your role has a lot to do with robust decision making, and employees with buy-in will try to resolve issues that impact the outcomes of their job.

What you’ll learn: whether a candidate is inclined to fully buy-in to their job responsibilities and make decisions that are in the best interest of the company. You’ll also be able to identify leadership potential or lack thereof.

6: Tell us about a decision that you made that was made based primarily on customer needs and input.

Is this person customer-centric? There are few roles today that don’t involve caring about the customer experience. Even staff on a production line must be focused on the quality experience for the end user. Companies are increasingly using customer feedback to improve their services and products and want to hire candidates who can turn customer feedback into actions. Asking this question will give insight into a candidate’s previous experience in doing this.

What you’ll learn: whether a candidate is creative, innovative and strives to improve the products and services they represent.

7: How do you accommodate last-minute changes?

Slotting in with the question before, being able to adapt to changes is crucial in any job. Team members and other colleagues should be treated just like customers, especially when managing projects because they never go as planned. By asking this question, you get a clear understanding of how a candidate deals with changes to a plan and whether they can make adjustments under pressure.

What you’ll learn: although this question is especially important to ask when hiring for more senior positions, in certain jobs junior staff must be able to roll with the changes. Some people become very stressed in an environment of constant change.

8: Tell me about a time when you worked under close supervision or extremely loose supervision. How did you handle that?

Some people dislike being closely managed, and others become insecure if they feel they don’t have a safety net. You need to find out how a candidate will perform under different types of management and what management style brings out the best in them. You’ll also get a good understanding of how internally motivated a candidate is because working in loosely supervised teams requires a degree of personal responsibility and motivation.

What you’ll learn: you can assess whether the candidate is a good fit for the team and line management style.

9: How have you handled working under someone you felt was not good at communicating?

Communication is vital. However, not everybody is good at it. Asking a candidate how they cope with coworkers who aren’t the strongest communicators is important. Every position, from entry-level to executive roles require sound communication. For senior and management roles, solid communication skills are essential. How a candidate handles poor communication is an indicator of how well they communicate.

What you’ll learn: you’ll get insight into the candidate’s communication skills, how they want to be communicated with, and whether their communication skills meet the requirements of the job.

10: At times your workload may feel unmanageable. Describe a time when you recognized that you were unable to meet multiple deadlines. What did you do about it?

All jobs come with deadlines, whether it’s responding to customer enquiries or meeting project goals. If you’re hiring for a position with a high workload, it’s vital that you ascertain whether a candidate can cope with pressure and prioritize their work. This question also ties in with communication skills. Will a candidate raise the issue, or wait until there’s a crisis before speaking out.

What you’ll learn: how the candidate handles pressure and whether they’re willing to speak up. This is a great starting point to dive deeper into the mindset of a candidate.

11: If you knew a manager is 100% wrong about something, how would you handle it?

Another one of those tough interview questions and answers might not come easily. Right versus wrong, assertiveness and communication are fundamental here. You want to know whether a candidate always does what they’re told or whether they dare to criticize their managers.

What you’ll learn: whether a candidate will fit intoyour company culture and the management style; not every manager appreciates an outspoken employee.

12: Give an example of a time when you faced an ethical dilemma at work. How did you deal with it?

At some point, everyone faces an ethical dilemma in their career. Knowing how to deal with it is an important skill to have and being able to act ethically is necessary across industries. This question gives insight into how a candidate reacts when their own morals are put to the test.

What you’ll learn: this exposes a candidate’s personal belief system and what they hold dear. Their answer will tell you if they’re a good fit for your company culture.

13: Tell me about a time you worked on a team with individuals from different cultural backgrounds.

Diversity in the workplace is essential, and most companies are promoting a more diverse workforce. You need to know upfront how a candidate will handle themselves in multi-ethnic and gender diverse environment. This question probably reigns supreme among tough interview questions and answers. You might not get an honest answer, so look for unconscious biases that might pop up. While this might be a little hard to talk about, it is necessary to find the right hire to fit your diverse workplace. Focus on ethnic sensitivities, and also whether the candidate has issues around diverse leadership and abilities.

What you’ll learn: a biggie, when it comes to tough interview questions because answers can be misleading, but if you listen carefully and ask follow through questions, you can identify biases.

14: What factors are crucial within an organization and must be present for you to work most effectively?

This is a far-reaching question that can give insight into what drives a candidate from within. If you’re hiring for a management role, you need to confirm that the candidate’s management style aligns with the company culture. All positions, however, require the right fit. Some applicants might prefer a participatory approach to management, which would not fit into a hierarchical driven organization or vice versa. You’ll also be able to ascertain whether a candidate is looking for promotional prospects or whether their focus is stability.

What you’ll learn: this question covers many bases, from leadership to fit; even if you’re interviewing for a junior post, this question leads you to candidate potential and whether they can be upskilled.

15: Describe a decision you made that was unpopular and how you handled implementing it.

Making unpopular decisions is, unfortunately, part of a manager’s job. When hiring for a management position, it’s crucial for you to find out how candidates handled situations where they had to make unpopular decisions. (Yet another of those tough interviews question and answers will vary.) You’ll be able to get a thorough understanding of each candidate’s management style for comparison to your role.

What you’ll learn: you can assess which of your candidates are a good fit for the role and also whether they’re a fit with the company culture and the team.

16: Tell me about a particular work-related setback you’ve faced. How did you deal with it?

Being resilient is of the utmost importance when hiring for a job in a fast-paced environment. It’s imperative for you to know whether a candidate can deal with setbacks at work because they’ll come along sooner or later. Candidates that have a hard time dealing with setbacks could either churn or turn into toxic workers, and that will also affect the rest of the team.

What you’ll learn: you can thoroughly assess the resilience of each candidate by understanding how they deal with setbacks.

17: Describe a time when your team or company was undergoing some change. How did that impact you, and how did you adapt?

It’s inevitable that systems, teams and companies will evolve and change is the only constant in many companies, especially the ones that do business in fast-paced environments and markets. Being able to adapt to organizational changes is a crucial skill to have to perform well and fit in the company culture. Unfortunately, some people fear change and become very stressed when new systems are implemented.

What you’ll learn: you get to know how a candidate perceives change and how they will cope in a continually evolving environment. You can judge whether the person will be a good fit for your situation.

18: What are the three most important attributes or skills that you believe you would bring to our company if we hired you?

This is another one of those tough interview questions and answers might not be honest. Candidates could tell you what they think you want to hear, so use some gentle probing based on their past experience.  If the candidate is relaxed, they’ll let you know what they consider their most important strengths.

What you’ll learn: you can get insight into what the person believes they can bring to the table, and this is usually the area that they have the most interest in despite their other skills.

19: Tell me about a time you set challenging goals. What did you do to achieve them?

When you’re looking for goal-oriented and results-driven candidates, this question is an important one to ask. It helps you understand how candidates determine their goals and how they work to achieve them. Being able to set realistic goals is an absolute must for certain positions, and this question helps you identify whether candidates can work with accountability.

What you’ll learn: how a candidate approaches setting goals for themselves, and if achieving a successful outcome matters to them.

20:What do you do to verify that your work is accurate?

When hiring for a position that requires a high degree of accuracy, this question is vital. Being able to check your own work is a necessary skill for many jobs, and this question helps you understand how a candidate approaches self-evaluation of their work and whether they are capable of doing this independently.

What you’ll learn: for specialist jobs, taking responsibility for accuracy is essential, so you’ll get insight into how a candidate manages their own checks and balances.

21: How do you compare and weigh pros and cons before making a decision?

Almost every job involves some degree of decision making, and many roles require thinking on your feet, particularly in sales and production. Even though snap decision making is important, the merits of the decision must still be evaluated. Specialist roles also involve weighing up options before proceeding.

What you’ll learn:you’ll get insight into how a candidate makes decisions and what processes they go through when evaluating different solutions to a problem.

22: Is it better to be perfect and late, or good and on time?

This question separates your specialist roles from creative and sales positions. In most cases, the correct answer is “good and on time.” Every product, blog post, and email can be tweaked to perfection, but it’s essential to know when to wrap it up and ship it. Most managers don’t want someone who’s unable to hit deadlines because they’re paralyzed by perfectionism unless extreme accuracy is pertinent to the role.

What you’ll learn: whether the candidate’s inclination towards perfectionism matches the requirements of the role.

23: What is something you’d be happy doing every single day for the rest of your career?

While it’s important to hire for skill, it’s also important to hire someone who’s likely to be happy in the job you’re hiring for. A question like this will help uncover what makes a candidate happy at work, which is a great way to gauge whether they’d enjoy their role and stay at the company for the long haul. (Sometimes psychometric assessment are good for identifying this type of thing.)

What you’ll learn: some essential job functions are tedious, and many people get bored. If the role requires repetitive work even to a small degree, you want someone who’ll be happy doing it.

24: Tell me about a time you disagreed with a decision. What did you do?

A dynamic company needs to encourage people to share their opinions and dare to disagree with one another from time to time. This question allows you to see how a candidate deals with differing views and whether they can adapt, mediate and respond to constructive criticism. Use this as a weakness behavioral question.

What you’ll learn: by evaluating the candidate’s response you should be able to tell if the candidate views differing opinions as constructive, as conflict or as an insult. Their reaction can also give insight into passive-aggressive or openly aggressive tendencies, which are undesirable in any environment.

25: Did your level of responsibility grow or change while you were at X?

This question can give some insight into the flexibility and performance of a candidate. If they started at a lower-level function and rose quickly through the ranks, they’re probably well performing and flexible. Increased job responsibilities matter, but the level of increased responsibility is more important, as is mentoring and training others.Again one of those tough interview questions and answers could be vague, mainly if a candidate has a history of poor work performance. It’s another weakness behavioral question. Sometimes a candidate might complain that they get overlooked for promotion. This could hint that there was some type of problem.

What you’ll learn: whether a candidate progresses in the workplace or if they’re an underachiever.

26: What is the biggest misconception people have about you?

This question is designed to probe the candidate’s level of self-awareness and their willingness to be honest and vulnerable. The first impression we have of someone can often be a misconception, and with this question, you can assess if the candidate has enough self-awareness to understand and manage the way others perceive them.

What you’ll learn: apart from self-awareness, this question ties in well with the previous one. If the answer to this question is a pity-party, it can confirm that the candidate is likely an under-achiever who shifts blame.

27: What role does your manager or supervisor play in your personal motivation at work?

In line with the previous two tough interview questions and answers that could be less than honest, this question sheds light on a candidate’s experiences in prior employers. This might help you understand why a candidate is looking for a new job and what they’re expecting from you as their potential new employer. You can understand what management style best suits them and gets them motivated. This helps you to find the right fit.

What you’ll learn: as a recruiter you want to understand how motivated a candidate is and where they get their motivation from.

28: Why have you had x amount of jobs in y years?

The answer to this question can tell you different things. It gives an insight into the candidate’s work history, what keeps them motivated, and what the factors were for deciding to leave. Furthermore, it also tells you something about their loyalty and their reasoning process. Are they easily bored? What is their attitude to hierarchy? It also gives the candidate a chance to explain why they jumped from job to job, if they did.

What you’ll learn: you could either be interviewing a slacker or someone who hasn’t found their niche yet. Probe further!

29: Why did you choose this profession?

Yet another of the tough interview questions and answers can be an economical version of the truth. Not everyone is in the career of their choice for a myriad of reasons. But that doesn’t mean that they don’t enjoy their career; it was just not their first choice. This can open the door to learning a lot about the candidate’s motivation, interests, education and ambitions. If a candidate rolled into a career out of necessity and is successful, it tells you a lot about them.

What you’ll learn: it can be clear that a candidate became focused on a career path even before they started working. Or, they’ve made the most of the opportunities that came their way.

30: Who is the smartest person you know personally? Why?

By thinking of a person they personally know, and articulating what they think makes that person smart, the candidate reveals their values and what they aspire to. This is beneficial information to assess if their aspirations and values are in line with the role you are trying to fill.

What you’ll learn: beyond the CV and the façade, what makes this person tick? We admire what we aspire to be.

Tough interview questions and answers to avoid

Unless you’re interviewing for a comedian, quirky, funny and trick questions don’t belong in an interview in my opinion. Candidates coming into an interview are both excited and nervous no matter what level they’re at. You don’t know the personality behind the CV that you’re interviewing, and asking silly and irrelevant questions can catch someone off guard and make them feel ill at ease.

A UK study found that 62% of professionals have been put on the spot with oddball questions, and 52% said they don’t like that approach in interviews. Although tech-giants like Amazon, Facebook and Google carry the torch for this type of questioning, interviewers should consider the candidate experience before trying to be cool.

If a candidate gives a wrong answer or doesn’t know what to say, they could feel embarrassed. Some candidates could feel slighted and lose interest in the position. There goes your best candidate (and your employer brand) because you asked them what type of tree they’d like to be, why a utility hole is round or why a tennis ball is fuzzy.

Whatever answer you get to silly and irrelevant questions tells you nothing about the candidate’s potential. Just don’t do it!

Additional resource: Check out our list of top 13 critical thinking interview questions to use

Want to spice up your interviews with some unique, fun questions? Download our free ebook containing 47 creative interview questions!

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