Master the Top 5 Hard Interview Questions and Get the Job

finding a job interviewing job search strategies May 20, 2023
Picture of 4 tacos of different kinds with the text

So it's time for your job interview. 

Are you ready to ace those notoriously hard interview questions?

You'll find them in almost every interview, but few people actually know how to answer them without B.S.-ing or tripping up.

In this article, we will cover five of the toughest ones and how to answer them — including the B.S. answer vs. the no B.S. answer that actually communicates your potential — so you'll be in good shape to handle them, no matter who's interviewing you.

Job searching is stressful, and job interviews can be hella intimidating, but with the right preparation and understanding of what employers look for in your responses, you'll have no problem tackling even the most difficult interview questions.

Let's dive into these challenging yet essential topics so you'll be ready to nail the interview and get the job.

Hard Interview Question #1: Why Did You Leave Your Last Job?

  • B.S. answer โŒ: Bluffing your way through it because you fear bad-mouthing your past/current job, company, employer, coworkers, etc. OR, answering generically in a way that doesn't provide much information, i.e., "I didn't see a path forward for growth."

  • No B.S. answer โœ…: Telling the truth, but not the whole truth. Be honest about why you left your last job (or why you're thinking about leaving), but leave out key details that identify specific people.

One of the very first tough interview questions you might get is "Why did you leave your last job?" It can be a tricky question to answer, as you don’t want to say anything negative about your former employer or colleagues.

The best course of action for addressing this question is to be honest and specific without feeling like you have to tell *everything*.

For instance, if your boss repeatedly refused your request for a raise, you can say your potential for growth in your position was capped and you had nowhere to go. 

If there were any challenges at your previous workplace – such as a lack of resources or conflicting priorities – don't pretend they didn't exist. Instead, talk about how those experiences have made you better able to manage competing demands and prioritize tasks efficiently. This shows that despite any hardships, you can remain dedicated to attaining success.

After all, even if things weren't ideal at your previous workplace, there were still opportunities for personal growth. Showing that you took advantage of these chances to learn new things demonstrates to potential employers that their organization would benefit from having someone like yourself on board who isn't afraid of taking risks, using their killer problem-solving skills, and pushing themselves out of their comfort zone. 

Finally, emphasize why this particular opportunity appeals to you so much more than staying where you were before. Whether it offers greater career progression opportunities or allows more creative freedom than before — make sure they know why they should hire you. After all, your awesomeness extends past your ability to check boxes for the job requirements.

Understanding why you left your prior employment can be a difficult question to respond to, yet it is an integral part of the interview process. This inquiry affords insight into how you think and act when faced with tricky circumstances.

Key Takeaway: Navigate uncertainties and spotlight the advantages when responding to questions about your past jobs; this will demonstrate to recruiters that you are a strong-minded problem-solver who can manage tough circumstances.

Hard Interview Question #2: Tell Me About Yourself

  • B.S. answer โŒ: Revisiting the points on your resume without adding anything personal.

  • No B.S. answer โœ…: Talking about who you serve and how you serve them. Add personal details, including how you got to where you are.

Another of the toughest interview questions asks you to candidly talk about yourself. This is hard AF for a lot of job seekers. It sounds halfway like the hiring manager wants to interrogate you like something out of CSI and halfway like they want you to share your entire professional history.

As it turns out, this common question definitely isn't about regurgitating your resume. Your interviewers have read that already — now they want to know more about you on a personal level.

That's why I recommend answering this question with an emphasis on your story. Who do you serve? How do you serve them? What problems do you solve? How did you get interested in the work you're pursuing? What was your professional journey? What are your interests in your field, and where do you hope to go?

You can tell your story without being long-winded or too detailed - that's very important since it's usually one of the first questions you'll get. It's a good idea to practice telling your story until you can sum it up quickly. Shoot for sharing this in 90 seconds or so and you'll draw in the hiring manager without boring them to tears.

Be candid and assured when responding to this question, but bear in mind that it's just the start of your interview. Now let's move on to discuss your weaknesses so you can showcase how they are actually strengths.

Key Takeaway: Your interviewers want to get to know you personally, too. Don't be afraid to share a few personal details that highlight your strengths, goals, and background.

Hard Interview Question #3: What Are Your Biggest Weaknesses?

  • B.S. answer โŒ: Talking about how your weaknesses are actually strengths. 

  • No B.S. answer โœ…: Talking honestly about areas where you need improvement, but also describing how you're learning to manage them.

Every time someone asks me what my top weaknesses are, it takes everything I have not to answer "Tacos and Diet Coke".

(No. That's not a joke. I even put that in my speaker bio.)

Being serious, the question is just such a hard one.  It feels invasive and icky and scary.

Here's the thing, though. When discussing your weaknesses in a job interview, honesty is key.

Be honest about areas where you could improve, but DON'T emphasize how you have turned your weaknesses into strengths.

When interviewers ask this question, they're not looking for a clever answer. They just want to know whether you have self-awareness.


People who can't see themselves clearly or who refuse to admit to their weaknesses/mistakes are often difficult to work with. They don't have the growth mindset necessary to work in a team or face challenges in the workplace.

Here's a better way to talk about your weaknesses: Take responsibility for them AND talk about how you're working on them.

For instance, if you find yourself challenged when it comes to interacting with unfamiliar faces or addressing a crowd, acknowledge that this is something you've experienced difficulty in. Then explain what steps you have taken to work on it such as taking classes or joining Toastmasters International. This shows employers that even though these are weaknesses of yours, they're not insurmountable obstacles and that you take initiative in improving yourself.

Finally, don’t forget about positive traits which could potentially become weaknesses if left unchecked - like having too much enthusiasm for projects which leads to one person taking on too much responsibility at once. Being aware of this tendency allows us to recognize when we need assistance from our peers instead of attempting everything ourselves, which ultimately makes us better team players overall.

By coming to grips with your weaknesses, you can strive to augment them and turn into an even more distinguished leader — one plenty of companies will want to hire.

Key Takeaway: Being honest and open about weaknesses, while taking steps to improve them, is essential in a job interview; this also applies to positive traits which could become weaknesses if left unchecked.

Hard Interview Question #4: Where Do You See Yourself In 5 Years?

  • B.S. answer โŒ: Coming up with a pretend answer about where you see yourself in the company after half a decade because you're not actually sure (no one is).

  • No B.S. answer โœ…: Honestly discussing the general goals you have for your whole career, including the milestones you want to achieve with those goals.

When you’re asked “Where do you see yourself in 5 years?” during a job interview, it can be an intimidating question. It requires thoughtfulness and reflection on your career goals and aspirations.

Consider where you aspire to be in your professional career over the long term. What would you like to be doing? Who would like to be working with? Who do you want to serve with your skills?

It's important that your response is realistic yet ambitious. 

For instance, when I was interviewing for a job with a software company, my simple answer when the hiring manager asked this question was, "I'd like to make cool stuff with cool people." (By the way, this was my answer to "Where do you see yourself in 5 years" for over 10 years.)

Additionally, emphasize what value you can bring to the organization if they hire you now: What are your unique qualities, and how could these contribute towards helping them reach their goals?

For example, if your current experience has been mostly focused on software engineering but also includes some project management tasks, mention how you, an obviously analytical person, can combine those skill sets in ways that will benefit the team both now and in five years when more complex projects come along.

Finally, remember that no one knows exactly what lies ahead, so don't feel pressured to provide a perfect answer. Be honest about where your career may take you over time while emphasizing why hiring someone with your qualifications now would still prove beneficial for their business even if things change later on.

This can be a difficult question to answer, yet it's imperative to consider your aspirations and objectives for the future. It also shows employers that you are motivated and have a plan in place.

Key Takeaway: No matter the job interview question, be honest about your goals and emphasize how you can bring value to the organization now and in five years.

Hard Interview Questions #5: Why Should We Hire You?

  • B.S. answer โŒ: Recapping all of your amazing qualities from your resume.

  • No B.S. answer โœ…: Tie all of your amazing qualities to the organization's problems and how you'll leverage your strengths to help solve them.

When it comes to why you should be hired, there are a few key points that can help you stand out from the competition.

The major key? Don't be "you"-centric when you answer this question. Instead, you need to demonstrate how your knowledge and expertise will benefit their organization - how you are the missing piece for their puzzle.

For example, showcase how you have used analytical thinking and problem-solving techniques to solve complex issues or develop innovative solutions in past positions — then talk about how those skills could translate to the organization.

You should also emphasize any leadership qualities that make you an ideal candidate for the role by highlighting instances where you took initiative on tasks or led successful initiatives at previous organizations. This could include taking ownership of specific projects, managing teams efficiently, and creating strategies that resulted in positive outcomes for everyone involved — including stakeholders outside of the team itself.

Finally, being able to adapt your answers depending on who's interviewing you is crucial.

For example, if you're interviewing for a project manager job and you're talking to the head of operations, you might talk about how your knowledge/experience will improve processes. You might even get into granular details about how. But if you're talking to the CEO of the company, you might talk about how your skills and expertise will ultimately help the organization make more money.

Overall, answering this question strategically will show employers why they should hire someone like yourself over other applicants; especially if they want someone who can hit the ground running right away.

Be Ready for Those Tough Interview Questions: Wrap-Up

Interviewing for a job can be daunting, particularly when you're confronted with those notoriously hard interview questions.

It's important to remember that the interviewer is looking for someone who can handle stress and think on their feet.

Take your time to prepare yourself by researching common questions and practicing how you would answer them. With enough practice, you'll be able to confront any difficult question with poise. Regardless of the outcome, remain upbeat and self-assured - it could be the key to securing that perfect job.

Are you a leader in tech looking to ace your next interview?

I'm here with no-nonsense career advice and solutions from 20+ years of experience to help you succeed. 

If you want to dig deeper into succeeding with job interviews, check out the Interviewing playlist on my YouTube channel.

If you need help preparing for your next interview, send me a message to inquire about my Interview Prep coaching package.

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