Coming up with insightful job interview questions is both crucial and incredibly hard. You need to find the sweet spot that lets you assess your candidates’ skills as well as predict how they’ll fit in with the culture.

Once upon a time (not so long ago), leading companies like Google were asking their candidates completely reasonable (not) questions such as ‘Why are manhole covers round?’ If this sounds utterly bizarre to you, you are correct: businesses realised that these questions didn’t give them an insight into a candidate’s abilities and soon phased them out. 

But the mystery remains: what are those elusive best interview questions to ask candidates? And how do you tell a great answer from a mediocre one?

We’ve compiled a list of our 16 favourite questions for interviews. Here they are!

1. Pitch our company to me

Instead of asking, ‘Do you know what our company does?’, try this’ it gives the candidate a chance to bring up any research they’ve done and it offers you a chance to see how well they’re able to handle an improvised business setting. 

What to look for in the answer: Look for signs that your candidate truly understands what the company is about. Goals, keywords, what’s unique about it, what it offers clients… 

Keep in mind, though’ answers to this question will vary wildly from one individual to the next. In general, people working or interviewing for sales roles, for example, will fare better than your average IT expert. And their reply will be more relevant when they’re expected to actually do this in their new position.

2. What’s your most remarkable career triumph this far? Be specific

You want to hire someone who is proud of their work and is confident in their abilities. But, on the other hand, you don’t want the answer to veer too far off into the realm of individualism.

What to look for in the answer: The perfect reply will show you that your candidate is at once a team worker and self-assured. What does this look like? If the applicant talks about an achievement in sales, are they focusing on themselves or are they highlighting how their achievement benefited the company?

3. Professionally, what have you done and not want to do again?

Everyone is bound to encounter a job, task, or project they simply hate. What really tells you something about a candidate is how they handled that circumstance and how they evaluate it now.

What to look for in the answer: The key here is this’ can the candidate find something of value or a catalyst for growth in the experience? The experts agree that answers to this question fall into one of the following three categories:

• Menial tasks: Let’s face it. No one likes organising a stack of papers. But this and other seemingly unimportant tasks are necessary for running a business. Your ideal candidate understands that they’re still making a meaningful contribution to the organisation.

• Hard tasks: Pay attention to the reasons they say it was hard. Are they blaming others?Was it a lack of planning or poor coordination? Would they do anything differently?

• Team tasks: Delve further into the team dynamics that were broken and what part your candidate had in them.

4. Talk about an occasion in which you set hard goals

The ideal candidate (yes, for any job) is results-driven and enterprising. Your business needs someone who can handle striving towards lofty goals and working under pressure.

Your candidate should show they are goal oriented. Follow up by asking what the goals were, what they did to achieve them, and what they learned from the process.

What to look for in the answer: The applicant’s reply should show you how their hard goals were more difficult than their usual work, as well as prove they can face a challenge without compromising the quality of their work. And, if the candidate explains how they failed, you’ve found someone assertive and self-aware!

5. Talk about your relationships with your past colleagues, both the worst and the best.

Before you hire someone, you need to figure out the tone of their relationships with others. Will they fit well in your team? This question helps you assess just that.

What to look for in the answer: A good answer will show you both the professional side (how they collaborated with others on projects) and the culture side (more focused on attitudes, morale, etc.). It should also be team-focused: not just talk about their personal likes and dislikes, but also how their colleagues’ attitude or personality affected their team.

6. Choose something complicated that you know well and explain it to me in 5 minutes.

Is your candidate smart, passionate, and charismatic? They should be’ those traits are great assets for your business and mean that, if hired, a person will have influence and be truly interested in their work. By asking this question, you’re evaluating just that.

What to look for in the answer: The best kind of answers will show off the candidate’s interpersonal skills as well as their intelligence. Can they understand a complex subject (whether it’s professional, a hobby, or just random facts) and explain it clearly?

Look for analogies’ explanatory comparisons that show they’re targeting their exposition to you’ as they demonstrate good problem-solving skills.

7. Storytime: Tell me one occasion in which you messed up

You’ve probably heard of this question before’ it’s pretty useful for determining just how self-aware your candidate is. The answer you’re looking for will show you that the person you’re interviewing is both humble and confident enough to admit to their mistakes instead of presenting a fake anecdote (like, ‘I’m too much of a perfectionist, so I pushed myself too hard’).

What to look for in the answer: The ideal reply has two parts. First, the candidate should admit to a real mistake instead of humble-bragging. This shows honesty and transparency.

Then, they should tell you what the experience taught them. If they see every crisis as an opportunity for growth, they’ll bring the same positive philosophy to your company.

8. What does ‘hard work’ mean to you?

This question is about pace. As a hiring manager, you want to find someone who will work at the same speed as the rest of the team. If you find someone who’s being underworked at their current company, a harder pace might be enough to tempt them into joining yours.

What to look for in the answer: Here, you’re not looking for hard evidence. Just make sure the candidate understands what your company’s culture sees as hard work and will be able to keep up. Also, a ‘work smarter’ philosophy is good: optimising processes is crucial for success.

9. Choose and explain: perfect but late vs. punctual and good enough

Maybe your candidate is the perfectionist, ‘I need everything to be exceptional before I turn it in’ type. Or maybe they’re more interested in meeting deadlines’ which is usually the case if they’ve already had to work in time-poor situations.

What to look for in the answer: Usually, a company wants employees that turn in their projects in time, even if they’re not the achievement of the century. However, don’t rule a candidate out just because they prelude their answer with ‘It depends…’ or ‘I haven’t worked with tight deadlines before…’.

Listen to their complete answer and make it a conversation: the applicant will be trying to suss out whether they’re doing well based on your attitude and feedback. Also, delivering on time is a skill that can be learned. You simply need to figure out whether your candidate is flexible enough to do it.

10. Out of everyone you’ve worked with, which percentage doesn’t like you?

Some folks are liked by everyone, but they might also be a doormat. Others are too assertive or otherwise less social, which results in fewer people being a fan. But there is a golden mean: you want to discover a candidate that works well with your team but who is also confident in their skills and work’ and this might cause a bit of friction.

What to look for in the answer: The percentage itself isn’t such a big deal. What matters is the answer to your follow-up question: ‘Why?’. The reasons the candidate gives for their detractors are key, so pay close attention to word choice.

Maybe, they say they’re too passionate or too detail-oriented’ that’s a good sign. A bad omen, instead, is a reply such as, ‘my coworkers say I’m absent-minded’. Look for self-awareness, too: someone who knows their flaws and works on them is a great addition to your team.

11. Who’s the smartest person you’ve met?

This question might seem a tad out of the blue, but it really isn’t. When you ask someone which is their goal as a professional or as a person, you’ll usually get somewhat standardised answers. If you ask this one instead, you’ll get a better view of what your candidate truly values and wants to achieve.

What to look for in the answer: The first good sign is that they can select a person on the fly and give an answer that makes sense. Then, the ideal reply would touch on skills and give situational examples. Say, ‘My ex- colleague Carla has an incredible ability to connect with new people. I remember when…’.

Maybe the crucial skill they highlight in their answer relates to valuable areas like fast decision- making, solid planning, or even a constant thirst for new knowledge.

12. What’s your most important decision of the past year? Why?

Especially if you’re hiring someone for a leadership role, decision-making skills are a crucial part of the job description. This question helps you figure out how your candidate approaches this sort of challenge from a real, situational perspective.

What to look for in the answer: It doesn’t need to be work-related. Maybe it was a big professional decision, like whether to take on a big project’ but it might have also been personal, like ‘should I buy a new house?’. What truly matters, here, is what the thought and decision process looks like. Did they agonise over it or did they make it quick? Was it a lonely decision or did they involve others? Try to understand the applicant’s priorities and long-term vs. short-term perspective.

13. If you had $50,000 to start a business of your own, what would you decide?

By this point, you think you already know a candidate. But their answer to this question can surprise you! Here, you want them to reveal their true dreams, interests, creativity, and values. Also, as you’re suggesting a specific amount of money, you’ll get a good idea of how good they are with money and business. How realistic is this person?

What to look for in the answer: The perfect answer is: creative idea + logistics. If they go into the specifics of how they’d make this happen (hiring, budgeting, etc.), you know you have a keeper.

14. Professionally, is there something you’d be happy doing forever?

You want happy, productive, and loyal employees, right? Then, you need to hire someone whose interests align (mostly) with the responsibilities of the position.

What to look for in the answer: There are as many answers to this question as there are candidates. What you want to hear from a successful one, though, is that they enjoy at least some part of the core duties that go with this role.

15. Is there anything in this interview that surprised you?

Hint, it might have been this very question.

Asking this gives you a chance to see how quick-witted your candidate is and to assess what their impression of the process is.

What to look for in the answer: Two things: specific and honest. The reply should highlight some particular, tangible aspect of the interview (such as an assigned task or even the interviewer’s clothes). As for honesty’ it shows confidence, especially if they’re highlighting something surprising about you, the key decision-maker.

16. Do you want to ask me any questions?

Yes, we’re revisiting the typical finale. While the candidate might have arrived at the interview already prepared to give an answer to this particular question, it’s still an important one.

Why? It reveals what is most important to them’ money or company culture? On-the-job training? Perks?

What to look for in the answer: Of course, there are no correct answers, but the candidate’s reply will help you figure out if they’ll be a good fit for your company and team, as well as how effectively and assertively they communicate their interests.

If you ask these questions during an interview, there is no guarantee that you will discover a perfect, long-term employee for your company. However, it’s a lot more likely to happen. Remember, insightful and relevant questions are the name of the game.