interview questions to ask

8 Critical Interview Questions to Ask

This article was last updated on April 23, 2019

If you’ve ever had to hire anyone, you probably have some rote interview questions to ask every person who comes in. However, many of the questions interviewers pepper applicants with aren’t particularly useful. To find the most motivated, successful, and dynamic employees for any job, try out these five interview questions (and a few bonus queries that are sure to help!).

8 Critical Interview Questions to Ask

1. “What kind of work do you like to do?”

This question almost never comes up, and that’s really too bad, because it’s one of the most important interview questions to ask. First of all, candidates are surprisingly honest when answering. They might tell you, straight up, that they prefer to grind away at their desk, or interact with coworkers on projects, or switch back and forth between assignments. How they answer is tremendously revealing about their work habits and how they might fit into your company.

Beyond being an important gauge of personality, however, is the fact that you can sort out who might be lazy, self-interested, or, worst of all, outright selfish. Don’t be naive – all employees are a little bit all of these things, as are you, but someone who might only be worried about their paycheck and not care about their team will probably reveal that in how they answer. If someone responds that they don’t want too much work, or that they seem too “independent”, be wary. You want to make sure your team is stocked with the most reliable kind of people. Ask this question to sort out it out.

2. “When was the last time you failed at something? What happened?”

This question is difficult for interviewees but great for managers. The thing is, everyone fails, and “if you’re not failing every now and again, it’s a sign you’re not doing anything very innovative.” Potential employees will rack their brains to find an answer both flattering and genuine, but in that process you are going to hear about how they dealt with making a mess of things, and what they did to pick up the pieces.

The best answers are the ones that are earnest. Some interviewees will claim they failed by being too good at something, and these people are liars. The ones to pay attention to are the people who are willing to admit a time they messed up, were able to recognize it, and then improve the next time around. Not only does this reveal an employee who will be willing to learn and not let their mistakes keep them down, but it also shows someone who isn’t so worried about their ego. These make great team members.

3. “Which of your previous jobs was your favorite? Why?”

This question is actually pretty similar to #1, except it will also highlight what aspects of a job an interviewee appreciates most. It’s a great culture question, and having employees that fit into your company culture is important to your mission. So, what kind of responses should you look for?

Some candidates will talk about the close friendships they formed with coworkers. Others might talk about how they liked the upward mobility and achievements of a previous job. A few might even mention they enjoyed the challenge of a position in their past. Even if they’ve built a resume that points strongly towards a certain type of job, asking this question will still be revealing.

Whatever they say though, there isn’t really a wrong answer. This one depends on, like I said, the culture of your organization. If your team is made of ambitious and driven individuals, you will want to pick someone who says their favorite job allowed them to wield those same attributes.

4. “What was your most stressful experience at your previous job?”

You can think of this question as an opposite to #3. This question will tell you what a candidate is least likely to handle. The fact of the matter is, all jobs have stressful situations, and usually a range of them. Some employees will be better at handling some forms of stress, while their teammates may struggle.

Again, this is a situation where there aren’t any specific wrong answers. Perhaps someone might show they aren’t a good match – say a common situation at your company is something likely to be difficult for a candidate to handle. In this instance, you probably shouldn’t hire them.

More important than what the stressors are, however, is how a candidate deals with them. Take, for example, Homer Simpson as the safety inspector at Springfield’s Nuclear Power Plant. He may have been hired to appease the local townspeople, but he was a perfect fit for Mr. Burns’ team. A dusty old energy baron, the last thing Burns wanted was an on-the-ball regulator breathing down his neck. Homer’s capacity to roll with the punches, not push himself too hard, and to be generally incompetent was perfect for the Plant’s team dynamic.

This isn’t to say I’d want to hire him, but understanding how an employee deals with stress, whatever that method may be, can help determine how well they’ll fit at your company.

5. “Why are you leaving your current company?”

This is actually a very common interview question, but I’m including it because it offers a useful window into what a candidate is like as an employee. Unless you’re interviewing candidates fresh out of school, everyone has a reason for leaving their last job, or wanting to leave their current one.Sometimes the reason can’t be helped – layoffs or family member needs to relocate, etc. However, and especially if a candidate currently has a job but plans to leave, their reasons might be dissatisfaction, conflict with coworkers or management, or they may be softly pushed out.

Regardless of the reason, pay attention to how an interviewee answers. If they begin to complain about their previous employer, or make any problems seem like all on the part of their old boss, you might have a difficult employee on your hands. Also, an interviewee answers that “they just weren’t that happy” or that they don’t know why they want to leave, you might have a waffler – someone who is unreasonably hard to satisfy.

What you are looking for is someone who acknowledges they’d like to move on, but they haven’t burnt bridges and aren’t looking to demonize their former or current employer. The day may come when this employee moves on from your organization. How they talk about previous employers is a good indicator of how they’ll talk about you, as well as how things might turn out with the interviewee should they join your team.

Bonus interview questions to ask

Those five should get you off to a great start, but here are a few more potent and fun questions to ask in your next interview.

6. “Tell me about yourself!”

This is another common interview question, but one that can work really well for an interviewer. Everyone’s favorite topic is themselves, and this question is so open it leaves room for them to impress, ramble, or even embarrass themselves. This will let you see how quick a candidate can open up, how they talk about themselves, and a bit about (or a lot about) their background and goals.


With this question, your job is to sit back, shut up, and let them go. If they are brief and guarded, that’s good information to have. If they go for 15 minutes and start talking about their childhood pets – also good information. If they talk any longer, go ahead and ask them to wrap it up. But the fact that they went on for so long, well, is also pertinent information.

7. “If you had to live on another planet in the solar system, which one would it be?”

This is one of my favorite interview questions to ask. Okay, it doesn’t need to be exactly this, but we recommend asking one off-the-wall question, and this is ours. Weird questions are good for a few things. First, they throw candidates off. They make them stop and say, “wait, what!?” And because it gets candidates off their bearings a little, it is also a great icebreaker. Instead of everything being so stiff and formal, it shows you have a little personality and they can relax a little.

It also acts as a chance to see more of a candidate’s personality than you otherwise would. If they respond with a funny answer, that’s great. If they are hesitant, you know that it might take a while for this person to warm up. Again, questions like this reveal plenty about an interviewee’s personality, if you know how to read the situation correctly.

8. “Can I borrow a pen?”

This final question is one of my personal gripes. If an applicant comes to an interview where they might be asked to write something, sign documents, or take notes, and they haven’t brought their own pen, it is a red flag. Think about it – if they aren’t prepared in this fundamental way because they forgot – or neglected to care – how will they pay attention to details on the job? It is a very little thing, and it shouldn’t necessarily disqualify an interviewee if they did forget. However, if there are other indicators that are less than great and they didn’t bring something to write with, my mind is made up.

Finding the perfect employee is never easy, but if you try a few of these out at your next sit-down with an applicant, you will be surprised at what they can reveal. By conducting efficient and revealing interviews, you’ll be able to find the right mix of motivation and greatness in your hires.

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