The 7 Toughest Interview Questions & How to Answer Them

If you’ve made it to the interview round during your job search, congratulate yourself! The hiring manager obviously thinks you could be a good fit for the position and wants to learn more about you.

Now comes the time to practice your answers to the questions you’ll probably encounter. Practicing helps you not only perfect your answers, but also sound confident while you’re answering their questions.

Here are some of the toughest questions to prepare yourself for and how to answer them:

“What are your weaknesses?”

Experts are mixed on the “correct” answer to this question—but most agree that the hiring manager doesn’t actually want you to share major weaknesses, especially those that are vital to the job at hand. Instead, take one weakness and put a positive spin on it, such as one you recognize that you have and discuss how you’re working to correct it. Oh, and don’t give a strength disguised as a weakness, such as “I am a perfectionist.”

“Why did you leave your last job?”

Employers want to see if you’ll talk badly about your former employer—so resist the urge to do so. Even if you left your last position for negative reasons, put a positive spin on it and stay professional. Perhaps the cultural fit wasn’t right for you or you were looking for the opportunity for promotion and felt it would be best to look elsewhere.

“Tell me about yourself.”

This is where your prepared elevator speech (a 30- to 60-second pitch about yourself) can come in handy. A hiring manager wants to hear about your accomplishments and traits that make you a good fit for the position. Keep it concise but compelling—they won’t have time for your life story.

“Tell me about the worst boss you’ve ever had.”

Again, this is a question where you need to resist temptation to divulge dirt on your past experiences. Take the high road and don’t vent frustrations during the interview. Making a broad statement such as, “I’ve had all types of bosses, and some were much better than others at managing and communication,” should be enough of an answer.

“Why should I hire you?”

To answer this question, you need to have a strong handle on your fit at the organization—which requires some research. Perhaps you see that the organization lacks a clear marketing strategy, something you have experience in creating and implementing. Depending on what you find and your unique selling points, answer confidently and show the hiring manager how you will benefit the organization if they hire you.

“Give me an example of a time when you had to [work in a team, think on your feet, work with a difficult client, etc.]…”

This is where the accomplishment stories in your cover letter and resume can come in handy. The worst thing you can do when asked to give an example of something is to panic and fail to come up with one. Come prepared with several stories that you can share about past experiences to show that you are capable in a variety of situations.

“Where do you see yourself in five years?”

Show that you’ve thought about sticking around the company and possibly moving up in the organization. Discuss how your skills and traits can help you excel at the current position and benefit the company in the future. Don’t share anything too personal, such as plans to start a family or travel the world, which could take you out of the running for the job.

These are some of the most common interview questions that job candidates struggle to answer. What other tough interview questions have you encountered? How did you answer them?

About Heather R. Huhman

Heather R. Huhman is the Career & Recruiting Advisor for Cachinko. She is also the founder & president of Come Recommended, the author of Lies, Damned Lies & Internships: The Truth About Getting from Classroom to Cubicle (2011), #ENTRYLEVELtweet: Taking Your Career from Classroom to Cubicle (2010), and writes career and recruiting advice for numerous outlets.

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5 Responses to The 7 Toughest Interview Questions & How to Answer Them

  1. Brian Cormack Carr June 3, 2011 at 3:55 pm #

    Great article, Heather!  Fear of “horrible interview questions” is one of the biggest blocks my clients face – I’ll definitely be sharing this useful list with them.

  2. Staffing Solutions January 26, 2012 at 2:37 pm #

    Well said Heather! I will definitely be passing this on to my colleagues in the staffing services realm as I know they too have a fear of asking “bad interview questions.”

  3. Tammy_daniels17 February 9, 2012 at 8:39 pm #

    great tips

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