How To Answer Difficult Interview Questions

While you don’t want to sound like a robot during an interview, preparation really is key to success, so it’s good to have previously thought about difficult interview questions that can arise. In this post I will outline some of the common interview questions that candidates can often slip up on, as well as some tough questions that we’ve heard people ask.

What’s your biggest weakness?

This is one of the most familiar and tough interview questions, and it is difficult to know which direction to take it. On the one hand, you are trying to show the hiring manager every positive side you have and ignore your negatives. On the other hand, showing your self awareness is a great skill to have and so being able to show that in an interview can be a huge advantage.

What not to say

Don’t turn it into a positive with something like “I’m too much of a perfectionist” or “I work too hard”. This is clearly a cop-out, and the interviewer will know it is.

This article from LifeHacker argues that if you try to answer like this, essentially implying that you have no weaknesses, “you’ve probably revealed your real issue then and there — a lack of clarity, honesty, and capacity for self-introspection”.

What you could say

The best answers we have found are where the candidate is honest, identifies that they are aware of their real weaknesses, and outlines what they have been doing to work on improving themselves.

Honesty is the first chapter in the book of wisdom — Thomas Jefferson

One way of doing this would be to use the STAR technique (Situation, Task, Activity, Result). This is a great technique that you can use to confidently answer most interview questions. This post by The Ladders outlines how you could use STAR to answer the specific question of your biggest weakness.

It is often claimed that this question itself is weak. Interviewers ask it for two main reasons; to see how you react to a tough question under pressure, and to get an idea of how your biggest weakness may affect your performance in the role. Using the STAR technique and using real examples to show that you are aware of and working on your weaknesses can go a long way to persuade the interviewer that they have nothing to worry about.

Talking about past successes / failures

During your interview, you will probably be asked to describe past situations where you have either been successful or unsuccessful. These are extremely common questions, and can again usually be answered using the STAR technique. However, it is important to note that the language you use to answer questions can be just as important as the idea or information you are trying to convey. Steve Pogorzelski, former Group President of Monster.com has been interviewing candidates for 25 years. He says that when asking about past successes or failures, he looks for two specific words. This idea is that if you are talking about successes, you should use the word ‘we’ and if you are talking about failures, you should use the word ‘I’. This shows the interviewer two things; you don’t simply take all the credit when things go well, and you are accountable when they don’t.

It is important to remember that failure is learning. If you can show that you don’t pass the blame onto others and that you can learn from mistakes, this will stand you in good stead.

However, bare in mind that different company cultures will be looking for different answers. If you are entering a competitive sales environment, the interviewer will want to know how much impact you had directly on previous deals. Riding on your teammates might not be such a good idea in this scenario, whereas if the company values teamwork highly then they will be looking for team players.

What do you want to do after this job?

The idea of a “job for life” is virtually non-existent now. Where in the past a successful career would have been staying at the same company for 30 years and slowly moving up the ladder, success is now often seen as having experienced many different roles at different companies.

Because of this, there is a balancing act that both the employer and candidate will have to overcome if this question comes up. The employer does not want the role to be seen simply as a short term stepping stone that they will have to be hiring for again in the near future, but they also have to realise that a successful candidate will have the ambition to grow their careers.

One take on this comes from Reid Hoffman, founder of LinkedIn, and Ben Casnocha, Silicon Valley-based entrepreneur / author. In their book ‘The Start-Up of You’, they argue that a job should be an agreement between an employer and employee. Under this agreement, the employee will work for a defined “tour of duty” to move the company forward in some way. In return for this, at the end of the ‘tour’, the employer agrees to help the employee grow and progress in their career. This would preferably be at the same company, but they recognise that this may not be the case and if not, the relationship would end on good terms.

What important truth do very few people agree with you on?

I have included this one as a slight curveball and one I cannot answer for you. As far as I’m aware it’s not a common interview question, but hopefully it will provide some food for thought. This is a question that Peter Thiel, founder of PayPal & investor in Facebook, says in his book ‘Zero to One’ he likes to ask in interviews. He argues that this is psychologically a very difficult question to answer, as you have to say something that you know is an unpopular viewpoint. He states: “Most commonly I hear answers like the following: ‘Our educational system is broken and urgently needs to be fixed’, ‘America is exceptional’, ‘There is no God’. Those are bad answers. The first and the second statements might be true, but many people already agree with them. The third statement simply takes one side in a familiar debate.”

A good answer takes the following form: ‘Most people believe in x, but the truth is the opposite of x.’

Peter Thiel’s own answer to this question is: “Most people think the future of the world will be defined by globalization, but the truth is that technology matters more.” So what is your important truth that very few people agree with you on? It would be great to hear some in the comments below. And you never know, with the popularity of Peter Thiel’s book you might find this question come up more than you think!

Do you have anything to add or ask?

This question will obviously come towards the end of the interview, and is a chance for you to ask for clarification on anything that may need it. However, it can also be a chance for you to stand out above other candidates and leave a lasting impression, as well as gauge an idea of your chances. This post on Big Interview argues “you should prepare at least two questions that demonstrate your interest in the position, your drive to excel in the role, and the fact that you’ve done some homework”.

What You Could Say

“What would success look like to you for this role?” — Lou Adler, best-selling author and creator of ‘performance-based hiring’, argues that you should not accept a job offer until the job expectations have been clarified. This is a great question to ask for two reasons. Firstly, it shows the interviewer that you are keen and eager to find out exactly what would be expected from you. Secondly, it gives you the chance to make a case for why you are a suitable candidate to achieve the specific expectations they outline. These two things could really set you apart from the competition. Also, looking further down the line, if you get the job, then you have clear objectives laid out and you know that you have been “hired based on your ability and motivation to achieve these objectives”.

Another way you could answer this question is asking about some recent news and / or public successes. This shows that you have done your research prior to the interview and are genuinely interested in the company. This would be an especially effective strategy if the interviewer happens to be a founder or the person responsible for the success. You would be surprised how proud people can be and how much they enjoy talking about their achievements.

Another question you could ask — “Do you have any immediate concerns that could prevent me being suitable for this role?” This is a bold one, but if you feel that the interview has gone well and you have built up a rapport with the interviewer then it could give you a great idea of what your chances are. It will also give you a final chance to clarify any misunderstandings if any concerns are outlined.

Bernard Marr suggests asking a question in a similar vein; “Do you see any gaps in my skills or qualifications that I need to fill?” — The benefit of this question is that if you are not hired then you can walk away with a tangible set of skills or qualifications to learn and improve in order to become more employable. Remember, you should always be learning.

I hope that these questions, answers and insights will help you in your job search and specifically how to answer difficult interview questions. Something to bare in mind — you should be thinking about all of these questions that could come up and how you might answer them, but you shouldn’t be preparing word for word answers. Your answers could change slightly depending how the conversation is going and the direction the hiring manager is taking the interview. Most of all you want to come across as authentic and personable.

What have I missed? Are there any other brilliant answers to these questions that you’ve tried? Or are there other tough questions that you’re not sure how to answer? Leave a comment below or tweet me @LiamNolan90.

Note: This post was originally published on 4th March 2015.