How to Answer Tough Job Interview Questions Expert Insights, Tips and Tools to Sell Yourself

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Become Team
Updated November 9, 2020

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Building a strong resume, choosing potential employers and getting your foot in the door to pitch yourself are huge accomplishments when searching for jobs. After all, only about 2 percent of applicants even get asked to interview, according to a report from Glassdoor, a job search and review website. Proper interview preparation is the crucial next step. Even the most qualified candidate can get shaken by an unexpected or difficult interview question. While it's impossible to know exactly what an employer will ask, examining tough questions, their purpose and ways to approach them can help job-seekers feel confident and prepared going into their interviews.

17 Tough Interview Questions and How to Answer Them

Thinking about potentially difficult interview questions in advance and taking the time to tailor answers to a particular company can go a long way toward making an interview go smoothly and helping a candidate stand out. Some of the toughest questions are quite common, pushing interviewees to think critically and creatively about their answers. Others are unexpected and may catch candidates off guard. Career strategist and founder of Rebuilding Foundations, Hannah Stenson, and master interview coach and founder of Rocket Interview, Jeevan Balani, weigh in on some of the toughest interview questions job-seekers face today.

Humans are complex and multifaceted, so committing to a one-word descriptor can seem misleading. It's tempting to choose a broad adjective, like “unique,” or an all-purpose, safe bet like “hard-working,” but such answers are generic and don't tell prospective employers much. Instead, interviewees should consider the specific position they are applying for and tailor their answers accordingly. “Pick something that is aligned with who you are and who the company is,” Stenson suggests. “For example, if they are innovating I wouldn't go with ‘classical' as my word. If you could boil down the best of you to pitch to the company, what is that one word?” Balani says an equally appropriate tactic is to choose a personal characteristic that doesn't change, regardless of setting. “Focus on a behavioral trait, like resilient, that speaks to how you go about getting your work done and potentially showing how you would be a good culture fit.” Strive to link that trait, whatever it is, back to the job or company.
Interviews are opportunities for people to sell themselves, but it's important to be strategic and connect their accomplishments to the position they're seeking. “This is not only an opportunity to show an achievement, but also to show what type of impact you like to drive,” says Balani, such as helping others' careers or growing the company's revenue. He believes a candidate can cite an accomplishment that's either professional or personal, but Stenson suggests keeping it in the work realm. “Did you climb Mt. Everest, start a nonprofit or save an endangered bird species? If not, keep it in the professional space. Candidates can easily overshare in interviews when they feel like the interviewer has asked them a personal question.”
“This is about showing value and character, and again showing how you align with the company,” says Stenson. The tricky part comes in making sure the right strengths are highlighted. Chances are, candidates who got called for an interview already have plenty of strengths that got them there. However, citing “creative thinking” as your most valuable quality when interviewing for an accounting position is a wasted opportunity. Instead, showcase a strength that is more relevant to that type of work. Balani points out that notable strengths don't have to be hard skills, either: “Behavioral strengths, like resilience or tenacity, are especially important and can be complemented with capabilities. An anecdote or two to bring them to life will also make them stick with the interviewer.”
The key to this one is sincerity. Presenting a positive trait as a weakness is a tired tactic that doesn't go very far with hiring managers anymore. Instead, job-seekers should be honest about their weak points and focus on the changes they are making to improve those weaknesses.
“This is a classic ‘tough' question since there is no perfect answer,” Balani says. “A good approach is to be candid about an area you are working on. But it is critical that you highlight how you have already started improving in this area, and the actions you continue to take to improve on this weakness.”
Stenson agrees and provides an easy-to-follow formula: “Go to WAR with this question: Weakness, Action, Result. My weakness is [a common weakness you experience and have learned from] which has forced me to [show maturity in how you have recognized it in your life] which has led me to [insert something positive about how you have grown because of it].”
Both stress that the weakness should be meaningful, not something trite (“I'm a perfectionist”) or trivial (“I need a couple cups of coffee before I get going in the morning”).
Rather than launch into an exhaustive account of interests and accomplishments, interviewees can treat this question as an opportunity to give their elevator pitch — a concise, professional rundown of who they are, what they have to offer and what they hope to accomplish. Balani recommends focusing on what drives you, and proactively answer why you want that particular job. “Tell them why you are there; don't wait for them to ask.”
“Candidates often feel they have to say ‘Hopefully being at your company' or anything very specific,” says Balani. “While specific can be good if you have a clear plan, often candidates are unsure. In that case, focus on the characteristics of the career situation you hope to be in at that point.” If you don't know whether you want to be working in marketing or HR, then talk about how you hope to develop your communication skills into leading a team in the future.
Also, recognize that while employers may be sincerely interested in a candidate's plans for the future, Stenson points out there's quite likely another motive. “Often the intent behind this question is about longevity — will you stay with the company, or will you leave? Positions are expensive to fill, and if you are planning to leave before you even get the job, that can be a red flag. Pivot the question to the here and now, and your commitment to this position.”
If the job they're interviewing for isn't the interviewee's ideal position, this question can be especially awkward to navigate. Even if the job seems perfect, you don't want to risk sounding disingenuous by listing your prospective employer as the best place you can think of. Balani suggests pairing your specific career goals with the qualities of the open position. “Frame up the characteristics of a highly desirable job and then connect the dots on how this job meets that criteria.”
When employers ask this question, they want to know that a candidate will handle uncomfortable situations honorably, discreetly and tactfully. Stenson suggests moving with caution when asked this question. “Do not overshare and do not throw people under the bus.” Focus on your behavior and response to the situation, and how you attempted to deal with it in the most honest and upstanding way possible.
Job-seekers who have been out of work for an extended period should expect to answer this question. Many employers consider employment gaps a red flag, since they may indicate the person was fired. Stenson and Balani agree that honesty is the best approach, and that job-seekers shouldn't feel guilty about their employment history. “Be candid, but do not apologize,” Balani advises. “If you took time off for personal reasons, just state that you did (and do not feel the need to be overly detailed), and then shift the focus to why this is the right time and the right opportunity for you.”
“How you talk about your current employer is a reflection of your character,” Stenson says. “There is no better way for people to let down their guard than to be asked about a job they hate.” Complaining about their former jobs, coworkers or employers won't put prospective employees in a favorable light, even if the grievances are valid. Balani suggests that interviewees focus instead on the opportunity they are pursuing.
Sometimes, employees have to make quick decisions without a thorough understanding of the situation. Interviewees don't want to come across as irresponsible or rash, so this question can be problematic. “This is about a broader problem-solving approach, so a candidate can highlight how they identify potential solutions, get insights across those solutions and ‘pressure test' the assumptions behind them,” says Balani. “Even if hard data for that specific problem is not available, a candidate can talk about how they get others to weigh in and how they pull from analogous problems where there is data.”
“This is a tough one,” Balani admits. “You can either punt to later in the interview process or frame up a range based on what you see as your worth. Too often candidates give a lowball number out of fear, and then get disappointed with the compensation, rather than indexing their compensation to the value they will bring.” It's also important to discuss the full compensation package, not just salary. Consider the hours you have to work, the amount of time off, health benefits, employee perks and discounts, commute time and other factors.
“What makes this prompt difficult is that it is often asked of candidates who have not formally managed others,” says Balani. “That said, the question is about ‘leadership', and candidates often forget about common situations where they may have demonstrated leadership by being proactive, and motivating and influencing others.” Candidates don't have to limit themselves to examples of formal leadership; any well-executed exhibition of leadership qualities will work.
Depending on the job, employers may want to know if prospective employees have the potential to move up the company ladder. Assessing a candidate's tact and thought processes when managing others can give employers a fuller picture of the interviewee's leadership and professionalism. Balani says this is a good time for an interviewee to show that they can hold their team to high standards, while also demonstrating empathy and grace in managing situations where performance is falling short. “In the case where candidates have done this, they should highlight why they let the person go and how they helped the person be successful in their transition. Often candidates have not [let someone go], so the thoughtful pivot is to answer the underlying question, which is how the candidate keeps a high bar for performance by demonstrating ‘what great looks like' and giving tough feedback when necessary.” Providing specific examples is crucial.
This question is meant to test a candidate's self-awareness about their strengths, weaknesses and overall approach. “It is best for candidates to provide clarity on the strengths that their colleagues have pointed out as well as their working style,” says Balani. “Stylistically, these strengths should be noted in an almost matter-of-fact sense instead of in the form of a sales pitch.” When preparing for an interview, job-seekers should consider many perspectives: How would their best friend describe them? Their former manager? Their mentor? Such insights can be valuable not only on this question, but on related queries about personality and abilities.
It's a straightforward question, but it can make interviewees nervous, especially if they aren't confident or feel uncomfortable selling themselves. However, the interviewer only has a short time to get to know a potential candidate, so this question can be a valuable opportunity to make sure nothing important is left unsaid. “You should be ready to show why you are the best,” Stenson says. “Do not mention the other candidates; this is a time to focus on yourself. Have a powerful, concise answer of why the company needs you.”
According to Stenson, this is by far the hardest question for an interviewee — in part because it takes a lot of thought and research to put together questions that are useful and convey genuine interest and effort on the part of the job-seeker. “Always, always, always have questions ready to go,” she stresses. “Do not make them answer questions that you could have Googled and gotten the answer. Ask questions about the culture, about the interviewer and how they like their job or the company, how success is measured in this role — questions no one but that interviewer can answer for you. If you do not bring questions, that tells me you do not care.”

Job Interviewing Apps and Tools

Practicing interviewing skills can help job candidates craft thoughtful responses and go into their interview feeling confident and prepared. These apps and sites can smooth the process.

  • Big Interview

    Big Interview is a subscription-based, online interview training platform that provides advice and practice interviews specifically tailored to users' industry, position and experience levels. Students and alumni can check to see if free memberships are available through their schools.

  • Charlie

    Doing extensive research on a company and the specific people in charge of hiring can be time-consuming, but it's a necessary part of building thoughtful interview responses. Charlie scours the internet and puts together a summary of pertinent news and social data regarding a company or person, giving interviewees a background upon which they can build.

  • Interview4.ME

    For those who prefer to practice their interview skills on a computer rather than through an app, Interview4.ME is a good solution. Users answer interview prompts and record them with their computer's webcam.

  • Job Interview Questions and Answers by Career Confidential

    This free app uses video to help users practice their interviewing skills. Users can watch as Career Confidential's CEO asks them interview questions, and make a video recording of their responses so they can see and hear their answers from the interviewer's perspective.

  • Monster.com Interviews

    This free app is a comprehensive interview prep tool for iOS. It provides practice questions, an interview playlist builder, pre-interview brain warm-ups and tips for post-interview follow-ups.

  • My Interview Practice

    This computer-based, free mock interview platform allows users to customize their interview practice to specific industries, and the site's question bank is updated regularly. Users can share their interviews with mentors or request feedback from an expert. My Interview Practice also has a blog where job-seekers can find more advice and information to help with job prep.

  • Pramp

    Aimed specifically at engineers and programmers, Pramp is a free peer-to-peer mock interviewing platform that helps prepare job-seekers for coding interviews. Users can interview, practice and give and receive feedback with a peer. Pramp also matches users' skills, based on practice interviews, with potential employers and facilitates resume-free interviews within the platform itself.

  • Wordzen

    While Wordzen won't provide any mock interviews or practice questions, it's an excellent tool for reaching out to prospective employers and following up after an interview via email. Live editors ensure users' emails are professional and free of errors, so a clumsy phrase won't quash a candidate's opportunity.

    • What If You Don't Have Some Answers?

    No matter how much they prepare, there is still a chance that prospective employees will not have an answer to an interview question — and will freeze up as they search for what to say. When a clear answer isn't available, the best approach is to be honest rather than try to fake your way through. Stay calm and poised, and try to work around the question while still providing the information the interviewee is after.

    Balani says it's good to think about the underlying intent of the question and address that. “Consider this example: ‘What experience do you have with SQL?' This is a common question for analysts, and often they do not have much experience. The way to pivot here is to discuss your relevant skills, which can include analyzing data and working with a variety of technological solutions, and to potentially articulate your understanding of SQL, even if you don't have the experience. Express enthusiasm for applying your transferable analytical skills to SQL.”

    Showing a willingness to learn, whether it's a particular skill or something related to the company's inner workings, is a great way for candidates to demonstrate honesty, sincere interest and investment in the position.

    Some companies like to ask word problems or trivia-style questions to see if a candidate can think on their feet and work through problems in stressful situations. If asked how many golf balls would it take to fill the room, a “would you rather” scenario or some other off-the-wall question, candidates should avoid saying they don't have an answer. In these situations, employers are more interested in seeing analytical skills than correct answers.

    “Pauses to think are OK,” Stenson says. “Not knowing the answer, especially to a more technical question, is OK as well. Walk them through how you would find the answer or as much of the answer as you know. These hard questions show them how you deal with stress and pressure, so recover by showing tact in this stressful situation.”

    If an interviewee finds themselves in a particularly tricky situation they can't handle in that moment, they should calmly acknowledge the question and say they need some time to think about it. In a follow-up email thanking the interviewer, include an answer to the tough question. While it's not ideal, remembering the question and demonstrating that they've actually given it thought can show that the candidate is thoughtful and true to their word.

    Stenson notes that it's important to remember that sometimes interviewers ask inappropriate questions about things like age, ethnic background, religious beliefs and gender, and that in these situations, it's OK to not answer. “Know what your legal protections are,” she says, “and learn to respond appropriately: ‘Is there something specific you are wondering or worried about?' Asking for the intent behind the question can help you clear up any concerns, no matter how awfully phrased the question. And at any point, if the interviewer is asking inappropriate questions, making you feel uncomfortable or disrespecting you or your time, you can leave.”

    Additional Resources

    People getting ready for job interviews can access more tips, preparation tools, mock interview software and other useful job search resources by checking out these websites.

  • Creddle

    Before landing an interview, job-seekers need to have a good resume. Creddle allows users to customize a range of sleek resume templates. The templates automatically format to fit a single page and can be printed or used online.

  • Glassdoor

    Glassdoor is a job search and review site that focuses on workplace transparency. Job-seekers can research careers and salaries to help prepare for salary questions.

  • Headspace

    This popular guided meditation app can help job candidates gather their thoughts and stay relaxed before their interviews.

  • LinkedIn

    This business-focused social media platform is full of job search resources and expert advice on tackling interviews.

  • Huntr

    Huntr is a job search organization app that helps job-seekers keep track of all aspects of their search, including jobs they've applied to and interviewed for, wage information, job descriptions, locations and contacts.

  • Mindomo

    For some job-seekers, assessing themselves and identifying strong talking points is a real challenge. Mindomo is a brainstorming and organizational tool that can help users visualize and connect ideas by using mind maps, concept maps and outlines.

  • O*NET

    Sponsored by the U.S. Department of Labor, O*NET is an excellent resource for career and salary research.

  • The Prepary

    This blog provides advice, templates, courses and other information to help job-seekers successfully navigate all aspects of a job search.

  • Visualize.me

    Using this site, job-seekers can make their resumes pop with eye-catching infographics based on information pulled from their resumes or LinkedIn profiles.

  • Rocket Interview Blog

    Find video and text-based answers to job interview questions and conundrums.

  • Interview Stream

    This interview training platform was designed specifically for college students to help them become stronger job candidates. The system allows professors and career coaches to customize training to specific fields of study and has a range of features to make providing feedback easier. Free memberships may be available through students' schools.

  • Princeton University's Career Services Department

    This is an example of an on-campus resource for student job-seekers. Many colleges and universities have career centers where students can draft resumes, research jobs and prepare for interviews.

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    Become Team
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    LearnHowToBecome.com is an advertising-supported site. Featured or trusted partner programs and all school search, finder, or match results are for schools that compensate us. This compensation does not influence our school rankings, resource guides, or other editorially-independent information published on this site.

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