5 tough interview questions and how to handle them

Interviewing for a new job can be stressful, but finding yourself unprepared for a challenging question might cost you the interview entirely.

Fortunately for candidates, the most challenging types of interview questions can also be the most common and therefore easy to anticipate. Sure, you’ll probably have to field your share of difficult, domain-specific questions that require technical or industry expertise. But what we’re talking about here are those potentially tricky, general topics that can pop up in any interview. They usually relate to how you operate in stressful situations, how you get along with difficult people, how you handle mistakes, and how you deal with your own shortcomings or limitations.

The point of these gotcha questions is usually to identify personality red flags, clarify concerns the interviewer may have about your resumé and give the interviewer a sense of how you respond under pressure. So, it’s important to come to the interview prepared for any of these. 

Here’s how to answer five of the most common types of tough interview questions without breaking a sweat.

Depending on your situation, you might get a different version of this question. (e.g., “Why are you leaving your current job?”)

Either way, you have to address the assumption that you wouldn’t be leaving if things were going extremely well.

In reality, there’s no such thing as a perfect job, perfect company or perfect employer, and there are plenty of perfectly good reasons to explore your options and seek new opportunities. Hearing your motivation for leaving (or whether your departure was voluntary) can tell your interviewer a lot about how you might fit in at their company.

The top reasons people quit their jobs are:

• Compensation
• Advancement opportunities
• Manager relationships

Often, it’s a combination of all three.

Ultimately, it’s best to be direct and succinct in your response to this question. If you hesitate, spend too much time contemplating or talk in circles, you’ll likely raise concerns. 

If you’re leaving for more pay, it’s important to convey that in a way that reflects a healthy sense of your value without coming across as greedy or mercenary. Even if you’re justified in deserving a higher salary, citing compensation as the only reason for job searching comes across as a red flag to potential employers. It can be OK to mention compensation as a motivator but cite other, non-financial incentives for why you’re looking for a new role.

Also, make sure to do your homework. Get to know the going rate in your market so you have a sound basis for your expectations. (More on this when we get to salary questions below.) Check reputable industry sites, such as the U.S. Bureau of Labor Statistics and Indeed.com, to start researching salary ranges for your role.

Looking for advancement in your career is generally a good thing; employers usually want people who are looking to grow with their company. Briefly speaking to why the advancement you’re looking for wasn’t available in your last company can help assuage concerns you might not have been promotable before or might be avaricious in your expectations.

Again, healthy self-advocacy is the best approach. If advancement opportunities at your last company were generally limited because of the company’s size or the long tenure of senior staffers, speak to that as matter-of-factly as you can. If, on the other hand, you’d been repeatedly passed up for promotion while others advanced, be cautious of sending the signal that your expectations outstripped your job performance. 

We know from well-published research that dissatisfaction with a boss is a leading reason people quit their jobs. In all likelihood, your interviewer knows this too.

According to Pew Research, 57% of workers quit because they felt disrespected at work.

Speaking to manager conflicts can be tricky because, while it could be that your boss was a jerk, it could also be that you’re hard to get along with or have problems with authority.

In reality, many factors inform workplace relationships. Maybe it’s not you or your manager but just a bad fit with the company culture, burnout that strained your relationship or a personality mismatch.

These things happen, and if you choose to speak about them in an interview, be mindful to show sensitivity, emotional intelligence and self-awareness.

One way to do this is to turn your experience into a learning opportunity. If your previous manager was too hands-off or distracted, for example, try framing it along the lines of, “Working for a company where I had a lot of latitude to achieve my goals taught me self-discipline and time management. It also showed me that I really thrive in situations where I have more guidance and mentorship.”

If your interviewer asks you about your professional strengths, you can bet you’re about to be asked about your weaknesses next.

How you speak about your personal and professional shortcomings says a lot about your mindset, so this question typically is less about your particular weaknesses and more about how well you know yourself and strive for improvement.

The thing to avoid here is the humble-bragging “I may just be too perfect” type of response. I’ve had scores of candidates try variations on the theme of “I’m too hardworking,” “I’m too loyal” or (and I swear this is a real example) “I’m so efficient, it makes people around me look bad.” Whichever variation is offered, it almost always sounds obnoxious.

Sometimes, these are actual weaknesses to manage, but if that’s the case, you should be prepared to give specifics.

For instance, if you tend to spread yourself too thin and burn yourself out, that can be a good observation to share, along with strategies you employ to manage that tendency.

An effective strategy for answering questions about your weaknesses is to couch them in terms of your ideal environment or best-case situation for managing them. If you don’t deal well with being micromanaged, for example, you can focus on your need for independence, which gives you an opening to speak about how you operate and succeed with little direction.

A common variation is, “What would your previous manager say is your biggest weakness?” This question is designed to gauge your awareness of how others perceive you. The catch here is that your prospective employer might actually have an opportunity to ask your last manager this very question in a reference call, so it’s a good idea to be reflective when addressing it.

That said, you can still apply the principle of framing your response in a way that speaks to your strengths and capacity for growth.

Whatever example you choose to share, be sure your answer demonstrates a fit for the role. Also, avoid oversharing. If you find yourself thinking about weaknesses that show a poor fit for the opportunity, you may want to reconsider whether it’s the right fit for you rather than attempt to talk your way around it in an interview.

While some positions have very explicit technical, credentialing or competency requirements, many job descriptions posted to major job-search sites include ambitious or even downright unrealistic lists of requirements.

Hiring managers often load up job postings with wish lists of qualifications, hoping to narrow the field of applicants to the cream of the crop as they imagine it. That’s why it’s good to get familiar with the exact requirements and nice-to-haves mentioned for the role in question, and then scrutinize how your own experience or qualifications align (or not). That way you’ll be ready if this question arises in your interview.

If your experience and training fall wildly short of what’s listed for the role, you likely won’t get an interview. So, if you’re answering this question with a hiring manager, it’s a signal you’re probably within the hiring manager’s expectations.

However, if you’re nervous about a few of the wish list’s bullet points, be ready to speak about them. For instance, if the listing calls for five years of experience in the same role, but you have only three years of experience, be ready to talk about the way your time in another role was similar enough to prepare you for this one.

Likewise, if your education is not in the required field, think ahead about how your experience or other education helped you develop the same skills or knowledge.

Overqualification can be a particularly frustrating problem to address. In general, hiring managers worry that an overqualified candidate will get bored, struggle with authority or perhaps be dissatisfied with the compensation offered.

At the same time, there are plenty of good reasons why a person with extensive qualifications might want to downshift to a less senior position. How you speak to this can make all the difference in demonstrating that your extra experience is an asset. It may be that your life circumstances have changed, for example, and you no longer want the added stress of managing people.

Or it could simply be that the market has few opportunities for positions at your previous level.

Perhaps you’re seeking better work–life balance than you had in your previous roles, or maybe you’re pursuing further education and want bandwidth to be able to focus on that alongside work.

There’s a delicate balance to strike in addressing overqualification, and the important message to get across is that you’re confident this role is the work you love doing and the right fit for you at this point in your life.  

When interviewers ask for examples of tough situations, what they’re looking for is a sense of how you handle stress and manage relationships. Will you listen to others and collaborate, or will you stick to your guns against all odds? Are you resilient in the face of opposition, or do you cave quickly?

Good answers to this prompt demonstrate a blend of emotional intelligence and fortitude. This might not be the right moment, for example, to bring up that one time you really frustrated a customer and held your ground. But then again, it could be if the situation worked out well for all involved and demonstrated your ability to turn around bad situations.

Look for an example that showcases your personal aptitude for reading emotions well and de-escalating conflict. If you found a way to strike a bargain that helped both sides, even better.  

For many of us, salary negotiation is the most uncomfortable part of job hunting. Negotiation is a specialized skill that requires strategy and practice, so it can be nerve-racking for the inexperienced.

Whether this question arises at the end of the interview process or earlier, it’s always a negotiation question. As a result, it’s important to address it with a mixture of confidence and market-savvy.

Negotiation experts are divided on whether you want to be the first to state a number or let the employer state their range first. The act of stating the initial number in a negotiation can have an anchoring effect, as it becomes the baseline number around which the negotiation revolves. If you anchor the number too high, you could put yourself out of the running, while a lower number could leave you with less than you could have walked away with.

If you’ve been in a particular industry or role for a while and you’re familiar with going rates, this can be more straightforward. You probably even have numbers in mind for your minimum requirement and the top end of the range. In that case, it may be a good idea to anchor the discussion near the top of the range, giving the employer room to negotiate downward, and taking your level of experience into consideration.

In some states, it’s now mandatory for employers to list salary ranges with job postings. If you’re interviewing for a role with a posted salary range and you’re not ready to negotiate, you might try simply stating that the posted range is acceptable and that you’d look forward to speaking more specifically about it.

When you reach the point of actually negotiating your compensation package, you’ll want to be ready with some proven negotiation tactics.  

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