How to answer 5 of the toughest interview questions

The better prepared you are for each type of interviewer, the better your odds are at landing a new title and office environment that’ll start your next lap around the sun on a positive foot.

Though it might seem silly or redundant to go over each and every last question that could be thrown at you, practice does indeed make perfect, especially when it comes to practicing interview questions and answers. Sharing your response out loud in front of a mirror — or to a trusted mentor or pal — will ensure you’re ready for anything.

Another way to sharpen your skills? Try to craft your own response to these super-hard and super-tricky interview questions from real professionals who managed to nail ‘em.

‘Do you love to win or hate to lose, and why?’

All is fair in love and war? Better to have tried and lost than to never give it a go?

The questions all land in the same arena, but when Alexa Garshofsky, a licensed real estate salesperson for Triple Mint was thrown this zinger, she was caught confused for a hot second.

The toughest aspect of the inquiry, she explained, was the lack of a so-called ‘right’ answer. “Whichever side you choose, you have to be able to convey your argument in a quick and concise manner, which can be challenging,” she said. Her approach was to illustrate her tenacity and dedication to creating the most optimal, successful results, making her someone who loves to go big.

“I went with what I felt would project me as the best candidate, especially in real estate. Companies want to know you are a closer and you will do whatever it takes to win,” she explained. Her reasoning must have won their hearts, considering she landed the job.

‘If I were a genie and could grant you three wishes in this next role, what would they be?’

While nearly everyone has been asked this question, it’s not a common one for job interviews, but rather, a sleepover favorite from high school or a first date curiosity.

That’s why media and public affairs consultant Rhonda Craig says this interview experience was her hardest, especially since the rest of the asks before had been generic and straightforward. Even so, she didn’t resist the curveball, and instead, went with it by laughing and buying herself some time by making references to her favorite movie, Aladdin.

Once comfortable on the magic carpet ride experience, she replied with her career desires: “The opportunity to take full ownership of a project related to the role, to help the company close a deal on a massive company merger with a specific company, and for more wishes, naturally.”

In the end, she was offered the position.

‘Sell me this pen.’

Sometimes the trickiest questions of all aren’t questions, but rather, challenges that force you to think on the spot.

As the founder of the 9 to 5 Project, Neely Raffellini discovered when applying for a sales role, it’s important to be prepared for anything, even when you think the interview was over.

“This was asked at the end of a sales interview when I was already exhausted! Of course, no one is going to ‘buy’ a pen unless they actually need it. That’s what made this question difficult. It was very abstract,” she recalled. She kept her cool and decided to emphasize the art of her convincing by reminding a potential customer that if they were in the market for a pen, this one would be the best bet for their money.

“I quickly outlined the features — color, ink style, cost — versus other options. Then, asked if they would have any objections to purchasing this pen when they needed one. The most important thing was to ask for the business,” she said.

Her tactic worked, and she went on to sell for the organization for nearly four years.

‘Tell me about yourself?’

When you took exams when you were in college, multiple choice answers were always preferred, since they at least give you a 25 to 50% shot at accuracy. Those open-ended paragraphs provided the most room for error, and the same goes for questions that force you to rattle off for a few sentences.

For freelance writer and blogger Kerri Hill, an expected interview question actually proved to be hardest.

“The difficulty was that I didn’t want to sound arrogant or narcissistic, however, I wanted my future employer to know that I was extremely confident in myself,” she said. Once she collected herself, she realized the answer wasn’t in overanalyzing, but in candor. “I answered honestly and confidently. I shared experiences that showed my eagerness to learn but how I persevered in difficult situations,” she said.

A few days later? She received and accepted the offer.

‘How would you measure our marketing efforts in this role?’

As every impactful marketer understands, campaigns are only worth their effort if they can be measured. That’s why so many employers are adamant about hiring employees who prioritize analytical guidelines and can effectively deliver reports, strategy advice, and creative visions to produce stronger results.

While freelance marketing consultant Melanie Long wasn’t surprised to be asked about how she would implement analytics when she was interviewing for a brand marketing position, she knew answering the question would be tricky. How come? It was nearly impossible to provide a genuine, accurate response without knowing the company’s current practices.

“I needed to know what systems were already in place: were they using email marketing? Social media? Before being able to give an actual recommendation, I had to know what was working, what wasn’t and where they wanted to go,” she said. Her solution was to answer a question with a question by inquiring about their current goal. From there she could give hypotheticals, but also illustrate her robust knowledge of this area from an honest place.

Though Long was offered another opportunity she couldn’t pass up and pulled herself out of the running at the third round of interviews, she felt her approach was the best one for the situation.

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