The Most Difficult Interview Questions (and Strategies to Answering Them)


Are you ready for an interview? Be honest – if you were, you wouldn’t search for the most difficult interview questions and ways of answering them.

Did you know that 81% of people lie in job interviews? Not a fact to boast of. And until job auditions replace traditional “question-answer” talks with candidates, you need to come up with a plan and methods to avoid telling the common lies and the consequences they may lead to.

But why is it that interviewing should always be a nerve-racking and sweat-provoking process? Is it some kind of a fun challenge for hiring managers to ask the trickiest question?

Here’s Why Recruiters Ask These Questions

A list of things they want to check:

  • Whether you’ve got any ambitions
  • Whether you’re a perfect match for the team and company’s culture
  • Whether your unique qualification fits the offer
  • After all, whether you’re the one for this position.

But communication with a recruiter may not be burdensome at all, if you start with proper interview preparation and master the art of answering the hardest questions with the strategies and expert advice below.

The Most Challenging Job Interview Questions and Strategies to Answer Those

Depending on the interview type (contract vs permanent, STAR, tech interview, etc.), questions may be both: tricky or plain simple.

Grab the most successful strategies to respond to 9 hard questions, 3 in each of the following categories: “Why Exactly You”, “Why Exactly This Job & Why Here” and “Diverse”.

“Why Exactly You” Category

Can you tell a bit about yourself?

A bit? How much? What exactly should I tell? According to the VP of Motivosity, Logan Mallory, “it is actually a “bridge” between your eye-catching resume and an interview. And since interviewers already know some facts, you need to summarize what you did in your life, but, more crucially, explain what motivated you.”

Strategy to answer:

Move from “what choices you made” to “why you made them”. For example, elaborate on why you chose a particular major and college or what made you change careers. Or why you took a gap year and went backpacking across Western Europe, somewhere outside Barcelona…

Can you name your dominant weakness?

This is a test of your honesty.

Strategy to answer:

Variant 1. Go with a ready-made answer. Check how to answer the “what is your biggest weakness” question.

Variant 2. Tell the truth.

Which variant would be better? If you select Variant 1, it would be a lie, most probably. And HR managers already know these answers pretty well. With Variant 2, it would be an honest reply with the stronger points.

Nobody is ideal. Tell about the factual imperfection you have and dwell on how you work on self-development and self-improvement. But don’t go critical exaggerating your genuine weak point.

Do you consider yourself stress-resistant?

Naturally, your employers are eager to find out how well you work under tense conditions.

Strategy to answer:

To demonstrate professionalism in handling distressing situations, you need to give a clear example. Portray specific circumstances and how you managed to overcome stress treating a conflict/problem with a cold mind. Name several techniques or practices you used to achieve that.

Or even go further than that – mention how oppressive and tense conditions helped you boost productivity and became a motivational tool to find the solution.

“Why Exactly This Job & Why Here” Category

Where do you see yourself in “X” years?

This question concerns your career expectancy and the level of your ambitiousness.

Strategy to answer:

Heed the call from Brian Dechesare, Founder & CEO of BIWS, who says that “Humbleness and modesty won’t lead you anywhere, similarly to over-exaggerated ambition and enthusiasm. Never say you’re the utmost match for them and that you’re 100% certain about it. Picture a mental image of yourself as a worker at the company and how both you and your employer may benefit from cooperation in the long run.”

Why should we pick you for this position?

A typical interviewer would sit cross-legged folding arms in a position that says: “I give you a chance to persuade me.”

Strategy to answer:

What you should never do: Never beg, concentrate on other candidates or say that you are better than anyone who has applied for this job.

What to do: Emphasize what benefits you can bring to the team focusing on your strongest points (make a list of your advantages that fit this vacancy beforehand). Keep it short – up to 2 minutes.

What are your expectations about the salary?

Putting this question, a hiring manager checks the consistency between your demands (and whether they are sensible) and their offer.

Strategy to answer:

“Three things to do here: prepare to negotiate, do research on salary at the company and general salary ranges, talk win-win,” suggests Gates Little, the President/CEO of altLINE Sobanco.

“It’s advisable to speak about a pay range rather than a precise sum and show that you’re ready to negotiate,” he adds.

“Diverse” Category

What’s your favorite book?

This question tests your uniqueness and individuality.

Strategy to answer:

Don’t mention: Textbooks and encyclopedias.

What book to speak about? The one that indeed spurred the greatest interest and gave some useful food for thought or helpful pointers.

How can you categorize these pictures on the wall (alternatively – any “brainteaser-ish” question) here?

This is the question I was asked during my first interview.

This one is from the category of puzzle-like questions with no right/wrong answer to check your problem-solving skills. Like the one with a Boeing 747 and the number of ping pong balls to get it filled.

Strategy to answer:

“Take a pause to think about it. That’s absolutely normal. Such out-of-the-box questions require some non-traditional thinking,” says Roy Morejon, President & Co-Founder of Enventys Partners.

“Clarify and put questions, if you need. Enumerate the steps of solving the issue. Sometimes, you may need a piece of paper to pen them down,” he continues. Get a glimpse here on how to reply to a brain teaser.

Is there anything you’d like to ask me about?

"No, I want to get out of here and breathe out." Wrong.

Strategy to answer:

Shawn Plummer, CEO of The Annuity Expert believes that “A “no” is showing you don’t care. And you’re wasting a huge opportunity to learn more about the vacancy. Be wise and inquire about the peculiarities of the company and the job and don’t ask a question that may be answered by googling.” Scroll through the top questions to ask at the end of an interview.

Ready for an Interview Now?

When a job interview is approaching, it’s mostly panic, anxiety and a great deal of sweating. And when a candidate hears “Tell about yourself”, it’s again panic, anxiety and even more sweating. Fear of failing often provokes lying which is one of the things that can end the interview.

Luckily, it won’t happen with you, because you already know some winning approaches to answering each difficult question during a job interview. Have a thoughtful job-hunting, stay motivated, and good luck in your interviews!

HRO Today Yoh Workers Confidence Index

About the Author: David Patterson-Cole is the CEO of the salary negotiation platform, Moonchaser,

Related Posts

From the mouths of recruiters – Part 1 Read Post 4 Relationships All Effective Recruiters Should Have Read Post From the mouths of recruiters – Part 2 Read Post