How to Answer 5 Tricky Interview Questions

May 18, 2021

Interviewing with a new company can be a significant source of stress for job-seekers. Candidates are expected to seem polished but not overly rehearsed, confident but humble, experienced but teachable. They know they might be pressed to explain career moves, or asked to “sell” their personalities and experiences as a great fit for the company. All the while, candidates are also evaluating the company with which they are interviewing, trying to determine whether there is a good cultural fit and whether it would be a strong career-advancing move. To help ease the stress of preparing for an interview, here are five of the most common interview questions, as well as examples of ways in which candidates might address them. 

Tell me about a specific problem you've faced that you've had to overcome.

For a question like this, candidates should be able to provide plenty of details. They should choose a problem that felt significant to their professional growth, that taught them something particularly valuable, or that they may be likely to face again in their industry, armed with experience that will help them better navigate it. For example: was there a scheduling snafu, material mix-up, or equipment failure? What were the risks to the final product and company’s bottom line if the problem was not swiftly resolved? How was the problem solved, and what did the individual and their team learn from the incident? Candidates should be clear about specific ways in which they contributed to resolving the problem, while using “we” language and giving appropriate credit when describing the team effort of working through and overcoming challenges.

What do you like least about your current/previous employer?

The most important thing to remember when preparing to discuss one’s current or previous employer is never to let emotions get in the way. Despite the slightly negative tone of this question, candidates should not attack their most recent employer or sound vindictive about or ungrateful for their time with the company. Instead, they should speak positively about their experience, while emphasizing what they’re looking for in an ideal workplace: opportunities for growth and professional development, more challenging projects, or the chance to diversify their career, for example.

Why do you want to leave your current employer? Why are you looking to make a career change now? Why do you want to change jobs?

There is some overlap between this style of question and the previous question. As in the previous example, candidates should plan to be positive about their current situation, but provide examples of what they are looking for in their next steps. It’s important to note that while money is a factor to be considered with every job opportunity, it should never be the primary motivator for changing jobs. Instead, focus on significant long-term benefits, such as opportunities for learning and growth. For example, if the prospective new employer has a top-notch reputation in the market, mention an excitement to work for the best. If it’s a newer company, speak to the challenge of growing a team from the ground up. And candidates should give specific examples of how they will add value to the new organization by making money, saving money, and solving problems. 

Why have you had [X] jobs in [X] years?

If a candidate has a significant number of job changes over a short time span, it will inevitably come up during an interview. Frequent job-hopping is not an automatic disqualification for a new opportunity, but it’s important that the candidate be honest and own their struggles and mistakes. Sometimes layoffs and project losses result in “last in, first out” turnover that is easy to explain to a new company. Other times, candidates may have changed jobs for a higher paycheck without considering the cultural and big-picture implications; as long as they tell the truth and own what they’ve learned from the experience, hiring managers are more likely to understand. Never make excuses -- learn from each change, and move forward positively.

How would your colleagues describe you?

While candidates do not want to sound over-rehearsed and come across as insincere when answering this question, they should give it plenty of thought before an interview. They can draw on their strengths and weaknesses as a teammate, a leader, and a subordinate. Are they excellent in client-facing roles, or exceptional problem solvers in high-pressure environments? Are they dependable teammates with a desire to develop stronger leadership skills? Or are they natural leaders who excel at bringing out the best in their teams? However the candidate is known for engaging with their colleagues, they should prepare to discuss that honestly with the interviewer. 

The key to a successful interview is preparation. Answering these five questions (and any others that may be asked), making a strong first impression, and moving forward in the interview process will be much less difficult if a candidate takes the time to organize their strengths, goals, and motivations before the first handshake.

About the Author

Mark Jones

Mark started working with Kimmel & Associates in 2000. He spent the first 20 years of his post-collegiate career in the commercial insurance industry, performing auditing, underwriting, and sales management. He eventually worked on the brokerage side, where the vast majority of his clients were contractors and sub-contractors.

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