Business Development

10 of the Toughest Interview Questions (& What to Ask Instead)



Conducting interviews can be a tricky task, as you have a relatively short amount of time to assess a range of candidates. Every interviewer is different and some really want to put the pressure on with tough interview questions.

While these can show how candidates work under pressure, there are alternative ways to phrase them to get a more genuine answer. Asking closed questions won’t lead to a good collaboration with your interviewee and a potential missed opportunity!  

Let’s delve into some of those tricky questions and give alternatives that can help your candidate to open up!


“Can you tell me about yourself?”

In terms of interview questions, this one is very vague and makes it hard for the candidate to kick things off. It’s often one of the first questions that the interviewer will ask and often involves a lot of umming and ahhing as the candidate tries to get their thoughts in order.

On the other hand, you may encounter candidates that take this question as an invitation to tell you their life story – including all the relevant information you don’t need to know. This can lead to a lot of rambling and wasted time for both parties.

Instead of starting with this old gem, get more specific. The first question should be a real conversation starter. You can pick a part of their CV to get you started, such as their most recent job, qualifications or personal statement.

Simply asking them to tell you more about these thoughts and experiences gives them a starting point, and you might find out more about their motivations and where their passion comes from.


“Where do you see yourself in five years?”

Another question that puts your candidate on the back foot, and this one can be interpreted in a variety of ways. You’ll usually get a short answer about hopefully working with your company and a lifestyle aspiration. Again, not very enlightening!

Take the initiative and ask them more about the qualities or skills they want to develop further. There’s no need to put a timescale on it. This can show you an authentic side to the candidate, as they think of the skills that they would like to build upon.

For some, this may be the likes of public speaking, leadership or further knowledge of the industry. A desire to learn and grow is a fantastic quality to find in your prospective candidate.


“Are you a team player?”

No candidate in their right mind is going to say “no” as the answer to this question! Almost every job requires you to work as part of a team or with others, so they know the value of this question. It’s a closed ‘yes/’no’ question that doesn’t give your candidate a lot to work with, other than being emphatically positive.

Take the lead and push them to tell you about teams that they’ve worked within. This gives you much more context on their background and previous workplace too. Ask them to highlight challenges that they’ve faces as part of a team and how they worked around these.

Team experiences never go perfectly, so there’s always plenty to talk about if you take this question in the right direction.



“How do you respond to pressure?”

The way in which the candidate reacts to the pressure of the interview effectively answers this question for you. A nervous candidate will most likely tell you through gritted teeth that they work well under pressure, as they won’t tell you something that could negatively impact their chances.

This also creates an implication that the workplace is stressful: they’re still in the interview stage and you’re ready to gauge their stress levels!

Alternatively, you can ask them to tell you about their biggest achievements in their current position or private life. This gives them an opportunity to boast about tasks they’ve completed – which will no doubt contain an element of pressure.


“Why do you want this job?”

Another classic question for interviews, this can be a hard one to handle. For many, they want the job for better financial standing or to get out of another work environment. These are fairly standard reasons, but they tend to be frowned upon in interview.

This will usually set off a load of mental gymnastics, as the candidate tries to think of other reasons to show themselves in a better light.

If you want to cut to the chase and get genuine answers, then you’ll need to elaborate further. Hone in on what about the job posting prompted them to apply and what they know about the company.

This isn’t a memory test; if the advert really resonated with them, they’ll be able to tell you all about it. This is also a good way to test how much homework they’ve done before they come to the interview.


“What are your weaknesses?”

This is a question that most candidates dread, as there’s really no right answer for them to choose! There are plenty of guides out there dedicated to how to answer this question for interviewees.

You’re pretty unlikely to get a real answer here: it will either be scripted or an unhelpful fact about their personal life. So, resign this question to the recycling bin and come up with something more inventive.

You could ask if there’s an area of their discipline that they want to gain more experience in, for example. They may have been pigeonholed in their current or previous position with the same tasks. They might not be experts at these tasks right away, but it takes a weakness to a strength in a flash.



“What did you dislike about your last job?”

This is another question that can be difficult to answer authentically, as the candidate doesn’t want to be negative. The truth may really be that they had a terrible boss or an issue with the work that they were given. In the interview however, they’ll try to gloss over this with a more positive reflection of the company.

A good way to turn this on its head is to ask what their perfect working environment would be. Understanding how they like to work and the types of boss they like can show if they’re a good fit for your environment.

This can also be useful to cross check some of the information that they’ve already given you in the interview. If they say they’re a self-starter but their ideal working environment contains a lot of hand holding, then something doesn’t add up.


“Have you applied for any other jobs?”

This question is a little too probing and doesn’t bring much to the interview. It’s tough for the candidate, as they don’t know whether applying for other jobs seems proactive or as though they don’t really care about the opportunity.

They don’t want to seem like they have all their hopes on one interview either. If they do answer positively, they will tend to be reticent with details about the other opportunities that they have applied for.

You can use the time that you would have wasted with this question to find out more about the candidate’s talents or ideal role.


“What makes you the best candidate for this job?”

The candidate doesn’t really have any context for this question, as they don’t know what the other candidates have to offer. This tends to be more of an exercise in self-confidence, than anything concrete.

They can touch upon their skills that are relevant to the job, but you can ask for this information in a much more direct way. Open it up and ask which elements of the job description they feel particularly confident that they can provide.

Follow up questions about examples and proven experience can also be demonstrated through this question, rather than a closed question about being the best for the job.


“If you were an animal, which one would you be?”

Many interviewers feel like they’re being quirky or interesting with this question, but the truth is that it has become almost expected by a lot of interviewees. It’s not relevant and there’s nothing much to be gleaned from their answer.

You can replace this question with almost any other that’s more relevant and targeted to the role.

Remember, tough interview questions aren’t always the best! The goal of an interview isn’t to make your candidate squirm, it’s to get to know them in an authentic way. To choose the right candidate for the job, you must get the right information by using the interview to ask questions that really matter.


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