https://www.nytimes.com/2020/03/13/smarter-living/how-to-answer-common-difficult-interview-questions.

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How to Answer Common Difficult Interview Questions

Don’t be stumped in your next job interview. These tips can help.

By Bryan Clark

March 13, 2020

In its simplest form, a job interview is an attempt to impress someone at the other end of the table. Your résumé and
qualifications got your foot in the door, but the in-person interview is where potential hires most often succeed or flounder.

“The interview is a better measure of emotional intelligence indicators, preparedness, punctuality, work ethic and all the
other little things that might make a good interpersonal fit,” said Kristin Sailing, a data scientist on the Talent Management
task force of the U.S. Army.

Though clearly important, these job interviews are also an exercise in managing anxiety. For 15 to 30 excruciating minutes,
you might as well be mounted under a glass microscope slide. You feel vulnerable, exposed. And then the questions start,
slowly at first but crescendoing with each new answer. Your brain struggles to find responses that don’t ring hollow or
come across as a cliché.

We spoke to several hiring professionals, asking each to identify the interview questions that commonly trip up prospective
employees. More than that, we sought to find ways to navigate the questions that seem impossible to answer in an attempt
to find ways to better prepare for them in the future.

We can’t quell the anxiety entirely, but a little preparation, you’ll find, can go a long way.

Tell me about yourself

It may seem simple, but our experts tell us that many people have a great deal of anxiety about this question. While most
interviewers use it as an attempt to break the ice, interviewees often have the opposite reaction. After all, you’re sitting
with a stranger who just asked you to open up. Should you use this time to tell her about your husband, or your two dogs?
Or is she asking you to tell her about where you’ve worked, your skills and qualifications?

The truth is, it varies. Most interviewers don’t think much about this question, using it solely as a tool to get you talking.
And while some may be trying to gain information, it’s not really about what you say, it’s how you say it. They might be
looking at your communication skills, for example. This is a golden opportunity to see if you ramble, or jump back and forth
between stories. Or maybe the interviewer is gauging your ability to frame key details of a story that’s understandable for
those who don’t know you.

But, chances are, it’s just an icebreaker. Don’t sweat it.

If you find that it’s a question you need to prepare for, try to focus mainly on career-oriented answers: your past
experiences, your qualifications and your ability to solve big problems. For example, maybe you instituted a weekly work-
at-home day in your department, a move that didn’t significantly raise costs while drastically lowering employee turnover.
This is a win that’s worth mentioning in this situation.

Where do you see yourself in five years?

Ms. Sailing believes this is another question that should be retired. The average person now transitions between jobs every
four years, according to the Bureau of Labor Statistics. And while it’s an antiquated notion, employers still tend to respond
negatively to “the idea that an employee wants to spend two to three years on a project and then move on to something
new,” she said.

“Who can really tell what the world will look like in five years,” said Chuck Edward, head of Global Talent Acquisition for
Microsoft. “I would be looking for a candidate to demonstrate how they are lifelong learners who embrace the future,
whether that be for the specific role they are applying to or for future opportunities.” He said that Microsoft was always
looking for “curiosity and a willingness” to learn, but also valued “resiliency and ambiguity.”

In a practical sense, you should focus less on where you’ll be physically or practically in five years, and more on what you
plan to learn between now and then, and how it might add to your set of skills.
What is your greatest weakness?
Of bad interview questions, this is the gold standard. Most of the hiring professionals we spoke with said that this was a
question they would never ask these days. Though it doesn’t mean other employers won’t, as you’ve probably already seen.
That’s not to say it won’t appear in other forms. Questions like “Tell me about a time you failed and what you learned from
it,” for example, offer an alternative to get the same information.

If you run into this question, your first reaction might be to answer the question by pointing out a weakness that’s actually
a strength — “I work too hard” or “I’m a perfectionist.” Don’t do it. “Both of these come across as insincere,” Ms. Sailing
said.

Instead, look for ways to pick an actual weakness, albeit a small one, and focus on the ways you’re trying to correct it. This
isn’t an opportunity to point out that you’re chronically late or often absent. Instead, focus on smaller, more manageable
weaknesses and what you’re doing to address them. “If you have to answer this question, you want to answer it in the
framework of pursuing self-improvement and growth opportunities,” Ms. Sailing said. If I had to answer this question, I’d
note that I am awful at estimating how long a project will take me to complete, and that leads me to take on more work than
I can handle. To remedy the problem, I’m currently taking a class on Udemy, an online education platform, to learn ways to
better manage my time and my work flow.

Mr. Edward agrees. He told us that he would be “looking for a candidate to show me how they might have leaned into their
weaknesses and created solutions to find success in a previous role.” Microsoft calls this “learning agility,” and Mr. Edward
said it’s an appealing trait for anyone he’s interviewing.

Alternatively, you could always point out flaws that aren’t related to the job. If you’re applying for a job as a software
developer, for example, you could mention that you aren’t particularly good at, or fond of, public speaking. This wouldn’t
often be a deal breaker, as public speaking skills aren’t commonly associated with software development.

Do you have any questions for me?

Both Ms. Sailing and Mr. Edward stressed the importance of turning an interview into a dialogue. It shouldn’t feel like an
interrogation, but a conversation. Look for ways to reciprocate interest, even asking your interviewer questions to learn
more about the company or the role.
“I enjoy when candidates ask thoughtful questions that push me to think deeper; that lets me know that this candidate will
make our organization and our teams smarter and more innovative,” Mr. Edward said.

Ask questions about the team itself: Who leads it; what does an average day look like; why did the person in the position
you’re applying for leave? In fact, asking for a tour of the work space, particularly the area where you’re stationed — as
well as an introduction to some of your future colleagues — certainly wouldn’t hurt.

Ms. Sailing and Mr. Edward agree that preparation is another key element they seek. “My bare minimum prep for talking
to vendors we might be working with to potential hires is taking a look at their LinkedIn profile and seeing if we have any
mutual connections,” Ms. Sailing said. Show an interest in the company by knowing its key players, mission statement and
some of its history. You should have a solid understanding of what the company does and how the team you wish to work
for aids in this mission.

“It might sound corny, but show you care,” Ms. Sailing added.

Interviews, as the saying goes, are where opportunity meets preparation. Preparation, in this case, is self-serving. Keeping
the interviewer engaged allows them more opportunities to offer information about the job you want. And when that
happens, you may just find them behaving as if you already have it.
Bryan Clark is a journalist from San Diego who lives at the intersection between technology and culture. You can follow him on Twitter @bryanclark.