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4 of the Toughest Interview Questions, and How to Respond

Deborah Swerdlow profile image

Deborah Swerdlow

A young woman sitting at a desk with her laptop during a virtual interview.

One of the most important aspects of interview preparation is having answers on the ready for some of the most common questions. Whether you’re great at thinking on your feet or you take a bit more time to thoughtfully respond, knowing what’s likely to be asked is a great way to present yourself as a strong and prepared candidate.

We’ve compiled a list of four of the toughest interview questions, and to help you better navigate them we’ve asked hiring managers and human resources professionals for details on what makes for a strong response.

Tell me about a professional experience where your integrity or moral code was challenged

This was the most common question that people submitted when asked to share the toughest interview question they’ve faced.

Carla Reed, Deputy Director of Human Resources at Community Change, said she has asked this question to get insight into how someone will behave in difficult situations. “We know oftentimes that past behavior is an indicator of future behavior,” Reed says. The exact answer Reed is looking for depends on the role she’s trying to fill, but as with any response, she’s seeking candidates who can be honest and open about past experiences while staying professional.

Pro Tip: Questions that start with, “Tell me about a time when…” are known as behavioral interview questions, and there are some straightforward formulas you can use to prepare an answer for any scenario you might get asked about.

Tell me about a time when you had to deal with a challenging or difficult personality at work

Here’s another behavioral question about a tricky situation you may have encountered in the past. When she asks this question, Reed says she’s looking for insight into a job candidate’s communication skills.

“Of course, not all employees or colleagues are going to agree all the time,” Reed says. “But are you someone who is going to fly off the handle and tell your colleague that they’re wrong? Or can you respectfully navigate your relationship with a difficult coworker?”

Pro Tip: This is a situation where there are clear right and wrong answers for how you deal with difficult personalities at work or difficult behaviors, such as passive aggression. If you haven’t always handled this situation in the best way, you can acknowledge that in the interview and explain what you would do differently today.

If you are able to create change in the world over the next 10 years, what will that impact look like?

This question is a twist on “Where do you see yourself in 10 years?” By focusing on the impact you want to create instead of the career status or other milestones you want to achieve, Reed says it helps her get a sense of whether her organization will be a good fit for someone’s goals and aspirations. It also usually gets her a more honest answer than if she asks directly about how the organization fits in with a job candidate’s career goals.

Becka Wall, Vice President of Digital Communications at National Immigration Forum, who has helped interview members of her team from the assistant to the deputy director level, has a different way of finding out if her organization is the right fit for a job candidate. She asks what may sound like a simple question: ”Why do you want to work at our organization?” and then listens closely to determine if a job candidate can articulate what it is about the organization’s work in particular that makes them want to work there.

“Many applicants think about the mission, but not the organization,” Wall says. Instead of more general responses about career goals, Wall wants candidates to talk about how the organization will help them advance their vision, or hear them discuss a recent campaign or project that moved them.

Where do you get your news from?

This question isn’t necessarily difficult, but it can throw you off in an interview if you’re not expecting it. Wall often asks candidates who they follow on social media, since that can be the digital equivalent of where you get your news. “It’s an interesting way to see where people are coming from and what their knowledge base is,” she says.

Tips for any tough interview question

No matter how much you prepare for your interview, you’ll probably still encounter a question that stumps you at first. We can’t predict the future, but Reed and Wall both offer suggestions for how to react when you’re faced with a tough interview question.

“You can always take a few seconds to pause and think about your answer,” Reed says. “Sometimes you can repeat the question or ask the interviewer to clarify, and then use that extra time to formulate a good response.”.

Wall adds that it’s okay to acknowledge that you’re thinking about it. “It’s fine to acknowledge that we’re only human and we may need a minute to collect ourselves before we answer a tough question,” she says. Acknowledging that you need a moment also illustrates that you’re thoughtful and willing to admit when you don’t have it all figured out already. Most hiring managers appreciate both the honesty as well as the desire to give a good response over a quick one.

“And when you do come up with your answer,” Wall adds, “say it confidently.”


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Deborah Swerdlow profile image

Deborah Swerdlow

As a nonprofit advocacy professional living in Washington, D.C., Deborah works with groups across the country to educate their communities and lawmakers about public policies that can help low-income residents make ends meet. She is passionate about helping people connect their interests to a cause they believe in and empowering them to take action.

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