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  1. Blog
  2. Interviewing
  3. February 21, 2023

Hard Interview Questions Are Easy with These Expert Strategies

Knowing what you want is key

Woman sits at office conference table answering hard interview questions
Photo courtesy of Tima Miroshnichenko

There was a popular job interview question making the rounds years ago: “How many windows are in New York City?” Sure, it tests analytical thinking, but what about a question asking to describe a time you handled a difficult situation (that you spent hours rehearsing the answer to)?

There’s also been “how would you rate your intelligence on a scale of 1-10?”; “what items would you bring to a deserted island?”; “how many basketballs can fit on a bus?”...

There are plenty of interview styles, so job seekers don’t know exactly what they’re going to get (although that is changing, as one of our experts shared…). You might have to tackle hard interview questions, or you might get to enjoy an easy breezy conversation with a peer. Either way, the best interview prep is becoming confident in what you want, where you want to go, and who you are (and working out any tech issues beforehand, if it’s virtual!) 

I talked to two experts who shared their advice on how to do that. 

New job interview trends to prep for

First, there are a few new trends in interviewing you might see when job hunting this year. 

One, as mentioned, is a more structured interview process, often used by some of the biggest companies. 

“There will be guides, instructions, suggestions on how to answer questions sent out ahead of time. You literally get the playbook of what’s going to happen,” says career coach and founder of The Career Edit, Leah Stallone. “They really want to level the playing field so everyone has the same tools and resources. Examples like using STAR stories to explain your accomplishments—they will give that to candidates ahead of time; they’ll say ‘this is how we want to hear your stories.’” 

The second trend Stallone sees is the exact opposite approach.

“Interviewing is turning more into a two-sided conversation, which I think is good. And what I mean by that is I think the best interviews these days really just sound like two industry peers talking shop. The candidates are asking questions the whole time. It’s really engaging for both sides. Sometimes I’ll even have candidates get off the phone and say to me, ‘I’m not even sure—was that an interview?’ It was—just because you were able to participate and ask questions doesn’t mean they weren’t able to get the information they’re looking for. 

“[It’s more like] playing catch with information,” Stallone says. “We’re brainstorming, we’re having conversations about what could happen, what we have seen, rather than a very pointed question-answer.” 

Stallone credits the interviewers for changing the process to be more like a conversation than an interrogation. (Anyone else picturing a man leaning back in a chair, holding your resume, asking “so why should we hire you?”?) 

“I think we’re getting more savvy interviewers, who are willing to push the limits as it relates to asking questions and being engaged in the process.”

COVID-19 has also reshaped interviews, adding more competition and tech needs.

“Now that more companies have shifted to a remote and/or hybrid model, there may be more competition from candidates outside of your local area than ever before, which is why it’s even more crucial to find ways to stand out,” says career coach and communication strategist Rowena Winkler. “Also, virtual interviewing and/or video submissions (as opposed to in-person interviews) have increased in the past several years.” 

Does this mean the end of the “how many windows are in NYC” question? Hopefully! But there are always simpler questions that can trip you up if you haven’t prepared to address them. Here’s how to tackle common hard interview questions and situations.

Read more: How To Answer: Do You Want To Tell Us Anything Else About You?

3 types of hard interview questions that stump even the best candidates

1. The interview question you have to answer with “no”  

Stallone says one of the most consistently hard-to-answer questions she’s seen for her clients, from junior employees to senior executives, is any question where the answer is “no.” 

“In an interview, you want to hesitate when you say “no” because it’s almost like a signal to people, maybe subconsciously, but they turn off, and they don’t hear the lovely information that you share after the ‘no,’” Stallone says. 

Of course, you shouldn’t lie and say, “yes, I’ve managed a big team before!” when you haven’t. Instead, learn to show your interviewer how your skills translate to what they’re looking for. 

“What I talk to my clients about is identifying what your personal ‘nos’ are,” Stallone says. “You can do that by looking at the job description. Identify the areas that you’re feeling are your weaknesses or that you’re less than competent in and break them down. 

“So for example, if this was a role that involved managing a team and you had not managed a team ‘formally’ before, that would be a ‘no’ for you. If I was to ask you ‘tell me about a time when you managed people,’ your first response would be ‘I haven’t.’ But what I would train you to do is to break down what makes up management. Management is made up of a lot of smaller pieces. It’s mentoring. It’s performance management. It’s delegation. It’s project management. All of these pieces. And then I really encourage my clients to look at questions with a glass-half-full mentality, and to speak honestly and truthfully, and to focus on the positive. So instead of saying ‘no, I actually haven’t done that,’ they would speak to the areas that they have done. It’s just getting into the thought process of what you can do to make this information more accessible to the interviewer.”

Similarly, Winkler says not to get discouraged if you don’t think your skills match the job listing’s requirements. It does not mean you are unqualified. 

“As someone who specializes in working with clients in the middle of a career pivot, I’ve observed that questions tied to gaps in skill sets and knowledge can be tricky for candidates to handle,” Winkler says. “Being able to translate the work you’ve done into skills that align with the job description is totally doable. The first step is to let go of the idea that you may not be qualified just because you haven’t worked in that particular field. Then, find ways to reword your experiences to better fit with the job description. For example, a teacher looking to move into marketing can say they have experience with ‘developing training materials’ instead of ‘curriculum development.’” 

2. The interview question that requires giving “evidence” 

Like a resume, it’s not best to simply list your responsibilities in a job interview. Interviewers want to hear more on what your actions yielded.

“Let’s say that you’re asked to demonstrate your leadership skills, or to describe your working style,” Winkler says. “Being able to not only provide a clear (and concise!) example to answer the question, but to also provide evidence, is super impressive to employers. How do you do this? By taking stock of what you did at previous jobs, and being sure that you capture specific stats, percentages, and trends alongside it. For example, being able to say that you demonstrate leadership skills by managing a writing team and growing blog engagement by 15 percent versus just simply saying that you demonstrate leadership by being a manager of five people.” 

3. The interview question about why you want the job

“I’d be great at it!” “It’s my dream role!” “You have amazing parental leave!” You might want to belt these out, but instead, Winkler says to think about communicating what you’ll deliver. 

“There has to be a value-add for the company within your response, but it should also be sincere. A lot of candidates respond how they think the company wants them to respond, and employers can see right through that. Instead, review the job description and the company’s website, social media presence, etc. and come up with a response that shows how your skills and expertise align with their needs.” 

Of course, you might not know if you’ll have to answer these exact types of questions (although they’re common, so be ready!). Here’s how you can be prepped for anything you get asked—and calm your nerves, too.

Read more: How To Answer: What Are Your Salary Expectations? 

The must-do prep to be ready for any hard interview questions

Stallone says the most important step is to know where you want to go, professionally. 

“I can’t emphasize enough to job seekers how important having a career target is,” Stallone says. “It’s so important. And I think a lot of times people skip that step in starting to look for a job, and then they wonder, ‘why isn’t my information getting anywhere, why am I not progressing?’ I liken it to throwing spaghetti against the wall. You need to be clear and direct, and know who your audience is. When you have that clear career target in mind of what you’re looking to do, whether that’s a role and an industry, then you use that as a strainer, to say what is applicable [in an interview].” 

Once she helps them clarify their career targets, Stallone works with her clients on their “accomplishment stories.” 

“Sometimes when people hear the word ‘story,’ they think it’s made up, or not factual. All of this is factual,” Stallone says. “You just get to present your angle with that target in mind. Otherwise we’re just including a myriad of information and facts, and it’s not in a clear storyline.”

This is why Stallone recommends her clients conduct a SWOT (Strengths, Weaknesses, Opportunities, and Threats) analysis of their careers. 

“A SWOT analysis is often used in business to look at your competitors and position yourself. It’s also incredibly useful as you go through the interview process. You have a library full of strengths, but when you’re preparing for an opportunity, you can literally assess which strengths would be most meaningful in that opportunity, and kind of keep those as your North Star, rather than including all your strengths, which seems very unfocused and untailored.” 

While the strengths and weaknesses are about your abilities, the opportunities and threats address the external environment. 

“That could be the market, that could be the industry, that could be what’s going on in the world around us,” Stallone says. “Doing research on that side going into an interview is one of those things that influences your answers and shows the interviewer that you’ve really done the research. So, that SWOT analysis is good to influence your answers, but I also think it’s good to influence your confidence.” 

A SWOT analysis also helps job seekers navigate interview questions that tap into what they fear are their weaknesses, or anything they’re self-conscious about. 

“Usually when we have a fear, we raise a red flag, and we shake it all over,” Stallone says. “The interviewer may not have even been aware or cared or worried, but now we’ve put it in their face a little bit, and now they’re wondering if they should worry about this. So I want people to address those areas as it relates to their tender spots. We all have them. We put them down to figure out how to address them in an interview without raising those red flags.” 

There are also interview logistics you can prepare for to remove some potential anxiety. If your interview is virtual or on video, Winkler says a few things will make it go smoothly. 

“One, place Post-It notes with potential responses/things to mention around the top of your computer near the camera so you’re looking at interviewers versus down at your notes; second, have adequate lighting and appropriate decor/backgrounds when you interview; and third, use technology such as Zoom, Streamyard, or iMovie to have the ability to edit and polish a video submission.” 

Once you know what you want to say and have your tech set up, practice! Do a mock interview to get a feel for talking about yourself and bringing up key points. 

“This can be done with a friend, family member, or mentor, or you can hire a coach to facilitate a session,” Winkler says. “The benefit to mock interviewing is the ability to obtain feedback in real-time on why your responses (or your energy or even your non-verbals) aren’t coming across in the way you’d like, as well as it gives you the structured time and space to revise responses so you’re better prepared and more confident.” 

Finally, don’t ignore the benefit of a good “power pose.” 

“I am also a fan of Dr. Amy Cuddy’s work, and have done power poses in the restroom or in front of my desk in my home office before an interview,” Winkler says. “By adjusting my posture in a way that exhibits confidence, I actually feel more confident going into the interview. I also take some deep breaths prior to interviews and give myself some affirmations such as, ‘I am the best fit for this job,’ and ‘I have work experience relevant to this job,’ and ‘I am worthy of employment.’

Now prep, practice, and get the job you want! 

Read more: How to Send a Job Interview Follow-up Email (with Examples)

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