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How To Answer The 7 Toughest Job Interview Questions With Confidence

Chris WestfallContributor

Business coach. Author of Easier and Leadership Language. Jul 13, 2023,03:46pm EDT


Finding confidence, when the stakes are high. GETTY


Job interviews may be on the rise, for workers looking for new opportunities. Last week, data from the US Bureau of Labor and Statistics showed the highest January-May jobs growth since 1939. So far this year, 1.57 million jobs have been added, and last month’s net increase of 314,000 jobs far exceeds results during the pandemic, according to CNN Business. “Overall, the job market is outstanding and is getting back to a balanced, sustainable level,” Chicago Federal Reserve President Austan Goolsbee said, in a recent interview. Joseph Brusuelas, chief economist at RSM, tells CNBC, “This is a strong labor market where demand for higher paying jobs is clearly the trend.” Meanwhile, a constant obstacle still exists for every job seeker. Namely, the seven most difficult job interview questions - and how to answer them with confidence.


The First Question You Must Answer, Before the Job Interview

Where does confidence really come from, in the job interview?


Most lists like the one you are about to read won’t tell you what you really need to know. But confidence - the ability to convey certainty, assurance and conviction in the interview - is the key to your success, no matter what questions you are asked.

If confidence matters to you, consider the difference between what you believe, and what you know. When it comes to your career, what are the things that you believe to be true? These beliefs would be matters of opinion, such as the belief that you are a hard worker or that you have the skills to do the job. While these beliefs may be true, and certainly all of our beliefs appear to be true, consider what it is that you know. Things that you know are not a matter of belief, faith, preference or expectation. Things that are known exist outside the realm of opinion, hope, or geography. Things that are known are things like the fact that you received your degree from Fordham University in 2006. Or that water boils at 212 degrees farenheit (if you are at sea level).

When you go into the job interview, do you speak of what you believe - or what you know? The answer might help you to discover where confidence comes from.

Applying what you know to be true, consider how you might approach these seven toughest job interview questions.


  1. Why don’t you tell me a little bit about yourself? This is a trick question. The real question is, “how can your personality and background be of benefit to me and this organization?” Knowing that personality can change, according to Psychology Today, you might want to change your perspective on your answer. Quoting chapter and verse from your Meyers/Briggs or DISC profile shows that you have taken a test, and exhibited some valuable self-awareness. Congratulations. Now: What’s the impact of your awareness? What have you discovered in your journey? After all, if being an INFJ was all it took to get the job, you’d already have it. Showing that you know yourself is good. Showing that you know how you can be of service to your employer is better. Connecting your life experience and personality to the job at hand is best.

  2. Where do you see yourself in five years? That’s an impossible question. What are you going to have for lunch next Thursday? Unless you are a caterer, that’s unknown - because we all know that the future is, well, uncertain. The fact is, when the future arrives, you will figure it out. Detailed plans, showing that you know exactly what 2026 is going to look like, are at best a speculation. So, how will you discover and decide over time what trajectory your career will take? How will you approach the future - not predict it? Start with what is known: the future begins right now. Always. A future goal (such as where you’d like to be in five years) brought into the present moment (right here, right now) is called a value. What are your values, right now, and where are those values leading you? The next five years may be a mystery, but what matters to you, right now, is something that is known. Does a path emerge from what you value most, right now?

  3. Why do you want this job? Every company, from Denny’s to the Department of Defense, hires one thing and one thing only. From the supply closet to the C-Suite, organizations are seeking solutions providers. What is the solution that you know you can provide? How does this position tie into your values? This question is an opportunity to talk about your commitment, and express what matters most to you. How does this gig align with who you are, and the solution you know you can provide?

  4. What is your greatest strength? Try answering this one with the same conviction that you might use to describe the way that gravity works, or the fact that horses stand on four legs. There’s no arrogance involved in describing what is known. And remember, false modesty is still false. As they say in Texas, “It ain’t braggin’ if you can do it.” If you say something like “creative problem solving” is a strength - how do you know? Examples and corroboration are key, when answering this question. Show, don’t tell, your greatest strength.

  5. What is your greatest weakness? There are some great answers from Harvard Business Review, Indeed, and other resources on this one. Remember, your interviewer has read those pat answers and scripted responses already. So, the resource that will help you most with this question is: authenticity. Here’s a chance for you to be vulnerable, and show your initiative. What would you do, if you loved your weakness? You would care for it - either taking a class to improve yourself, hiring a coach, outsourcing that task to someone more qualified, or aligning yourself to focus on other things. Fall in love with your weakness, before you answer this question, and your response will show that you are taking the kind of action that aligns with your values. Start with authenticity, and add action, and you are on the right track.

  6. What is your purpose? Questions that are as broad as all outdoors are always tough. If an over-arching grand vision for your career feels like a bridge too far, remember: you already know how to answer this one. Take a look at your values, and see if a purpose starts to emerge. Be careful not to make some bold and unsupported aspirational claim - unless “fake it till you make it” is your purpose in life.

  7. Why should I hire you? Without any intrusive thoughts, consider the service you know you can provide. Consider how you might answer this question if you weren’t on your mind. It’s hard to do, because we often fall into a misunderstanding. Applicants think that the job interview is about them - the person applying for the job! But it’s never about you. It’s about what you can do. More specifically, what you can do with, through and for others. So, without subjective mental chatter or personal opinion, what do you know to be true about the solution you offer, the contribution you make, the values you possess, and the impact you can create? Speak as if you were a scientist, describing a hypothesis and a related experiment. The scientist has no regrets, shyness, or limiting beliefs around the experiment. It’s just an experiment! And here’s what is known and not a matter of belief: experiments never fail. Even if the hypothesis doesn’t work out, the experiment isn’t a failure. Because a good scientist is always more informed, regardless of how the experiment turns out.

What is Known, in the Job Interview Process

The job interview process is a series of experiments. Sharing your story may not be easy, but there’s a way to make it easier. Start with what you know, focus on service, and speak from a place of conviction. Projections about the future are tough for anyone to tackle, so bring those aspirations back into the present moment. Open up about your values. Start there, and you just might discover that you find yourself being valued - above the other candidates.


https://www.forbes.com/sites/chriswestfall/2023/07/13/how-to-answer-the-7-toughest-job-interview-questions-with-confidence/?sh=50a99d5666c5

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