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July 6, 2023

3 Hardest Interview Questions You’ll Need To Answer To Land Your Next Job

For most of us, interviewing is an uncomfortable and nerve-racking experience. The stakes are high, and we worry we’ll fumble the opportunity to land that next big job. But here’s the good news: interviewing is a skill, and so much of putting your best foot forward and distinguishing yourself from other candidates comes with precision […]

For most of us, interviewing is an uncomfortable and nerve-racking experience. The stakes are high, and we worry we’ll fumble the opportunity to land that next big job. But here’s the good news: interviewing is a skill, and so much of putting your best foot forward and distinguishing yourself from other candidates comes with precision and practice.

Ludovica Colella, a therapist and coach dedicated to empowering women to up-level their confidence, emphasizes, "The prospect of job interviews often brings about anxiety as we face real judgment and evaluation. However, it's important to keep in mind that true confidence doesn't stem from having all the answers; it lies in embracing yourself even when you don't."

So, why not get started by tackling the questions that might throw you for the biggest loop? Here are the three hardest interview questions and how you can nail them.

1. Tell me about yourself.

Most interviewers start with a seemingly simple question: Tell me about yourself.

It seems so straight-forward that inexperienced interviewers may not spend time preparing to answer it— after all, who knows more about you than, well, you?

But once you’re actually on the spot and the nerves set in, this question is so open-ended that it makes it easy to ramble or provide an unclear picture of who you are professionally and in context of the job for which you’re applying.

While you want to add personal elements and spark organic conversation, everything you mention should help convince the interviewer you are the right person for the job.

Here’s a structure you can follow:

Share a story that demonstrates your career interest.

You don’t stand out in an interview by sharing what’s already on your resume. Instead, shake things up when you get the usual, “tell me about yourself” by sharing a personal anecdote that relates to your skills and interest in the position you’re applying to.

Here’s an example from a client who wanted to break into the corporate side of luxury hospitality:

I didn’t grow up in the lap of luxury, but my dad always collected Starwood points and allowed me to spend them all on one night at a hotel of my choice each year. I spent months researching hotels and would count down for the occasion…I became so enamored by luxury and beauty that I worked all sorts of jobs in hotels throughout my adolescence.

Share the most important skill(s) you possess that will help you excel in the role.

Now that you have the interviewer’s attention, let them know how you can meet their needs or solve a problem that they have. It’s always more effective to share what other people have noticed about your skills, so if possible, speak in testimonials like this:

Now that I have my Bachelor’s degree in Business, as well as a few internship experiences in marketing, I’m ready to contribute to the vision of a cutting-edge hospitality brand. Throughout each of my work experiences, I was often told that I was a very detail-oriented and innovative employee, which I’d love to apply in my next role. In fact, I saw on your website that you’re advertising X. I looked at what your competition is doing, and I saw that they have this interesting campaign doing Y… If I joined the team, I’d look at how we could do something even stronger, such as Z.

Explain why you want to work at this company, specifically.

If you can clearly communicate why you want to work for this company as opposed to any other, you’ll be one step ahead. Reference the company’s mission statement, client roster, press coverage, and/or corporate responsibility to speak about why they’re so special. Do your research!

Here’s an example once again from the same client:

I’m looking to take on a marketing role that allows me to constantly be challenged, learning and growing. I’d love to be a Marketing Director for a brand like yours someday, and I think it’s great to start here and learn everything that I can about it.

2. What’s your biggest weakness?

This is one of those classic interview questions that feels intentionally tricky. While you may already know what not to say (i.e. “I run late often” and “I lose enthusiasm over projects I don’t care about”), you may still be wondering, what is a good answer that still sounds sincere? You need to learn how to impress your interviewer by sharing a weakness.

The best way to approach this question is by providing a quality or skill that is malleable— meaning, something you can work on. The best way to frame your answer is by:

  • Identifying the weakness/challenge
  • Contextualizing why you’ve had this challenge in the past
  • Providing a clear plan of action to address your weakness/ challenge

Here are a couple of examples; and keep in mind, the weakness

Example 1: Public speaking

One area I've been actively working on is my public speaking skills. In the past, I used to feel nervous when presenting in front of large audiences. However, I recognized this as an opportunity for development and took steps to overcome it. I enrolled in a public speaking course and joined a Toastmasters club, where I actively practice and refine my presentation abilities. While I've made significant progress, there is still room for improvement, and I'm committed to further enhancing my public speaking skills to become a more confident and effective communicator.

Example 2: Lack of experience in Salesforce

One area where I recognize I have limited experience is in working with Salesforce. While I have a solid understanding of customer relationship management systems and their importance in streamlining business processes, I haven't had the opportunity to work extensively with Salesforce specifically because my previous company used another technology. However, I am a quick learner and I believe that with my analytical skills, I can adapt to new software quickly, and become proficient in Salesforce. I am eager to embrace any training or resources provided by the company to ensure I can contribute effectively and efficiently in utilizing Salesforce to its full potential.

3. Where do you see yourself in five years?

Whether it be through PTO, 401K match, or a wellness stipend, most companies look for ways to appeal to workers so they can avoid quick employee turnover rates. The fact is, training new employees comes at a cost, so it’s in their best interest to keep you around however long that may be.

One subtle way that employers ensure high retention rates is by weeding out workers who are not set out to grow with the company before hiring them — and they do this by asking: Where do you see yourself in 5 years?

If you find this question difficult to answer, you’re not alone. Data suggests that most workers — especially young workers — leave their job before 5 years. Given this fact, we can assume most job seekers’ sincere response to this question is not appealing in an interview setting.

But carefully crafting your answer can leave your potential employer confident you see a future with the company … regardless of your actual career plans. This is crucial for landing a job.

Here are a few tips for communicating your commitment to the company:

  • Focus on personal growth. Emphasize your desire to develop a specific set of skills and knowledge within the respective industry.
  • Align your goals with the company. Showcase how your aspirations align with the company’s long-term vision and objectives. (i.e. express an understanding of the company’s values and why you see yourself committed to those values for the foreseeable future)
  • Express enthusiasm for the role– and not where it can take you. Show genuine enthusiasm for the position for which you’re applying and explain how the job itself is exciting for you. While it’s helpful to show how it plays into your career vision, you want to sound excited about the role at hang, and not in the mindset of trying to use it as a tool to go elsewhere. In fact, discuss how you envision taking on more responsibility and contributing to the company’s success.

By preparing for the toughest interview questions, you can boost your confidence and leave a lasting impression on your interviewer. Take time to familiarize yourself with common, difficult questions like the ones above and craft thoughtful responses that let your true potential shine during your next interview. And like anything, practice interviewing.

Article written by:  Orville Lynch, Jr.
Mr. Lynch, a member of the legendary two-time Ohio Civil Rights Hall of Fame Award winning Lynch Family. Mr. Lynch is a nationally recognized urban media executive with over 20+ years of diversity recruitment and serial entrepreneur with numerous multi-million dollar exits.
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