How to Respond Effectively to Tough Interview Questions

I’ve coached many job seekers, and most of them have expressed some anxiety about being interviewed. Some of the anxiety comes from knowing that the hiring decision will largely be based on their performance in the interview situation, which by its nature tends to be quite different from doing the work of the job, and which can only give a limited view of them as a candidate. Some anxiety comes from not knowing which questions will come up, and feeling pressure to think and speak on the spot in a compelling way. But perhaps the greatest anxiety comes from dread of getting asked tough interview questions—questions about weaknesses, shortcomings, failures, and other unpleasant topics that you’d never include in a résumé.

In this article, I’ll share some thoughts that may help you get a new perspective on tough interview questions, and help you prepare to respond to them in a way that convinces interviewers that you’re a great choice for the job.

Why Do Interviewers Ask Tough Questions?

Given how uncomfortable tough questions can make you feel, you might wonder if the people who ask them have sadistic tendencies. Though we can’t prevent all sociopaths from becoming interviewers, the vast majority of interviewers are reasonable, empathetic people who have perfectly valid reasons for asking the tough questions. Most of the information they will have gathered about you before the interview will be biased toward the positive—the achievements you listed in your résumé, the glowing reviews you included on your LinkedIn profile, the enthusiastic testimonials given by the references you provided. In order to get a complete perspective, interviewers need to also know things about you that might not be so wonderful, because they need to know what gaps might need to be filled, what coaching you might need, and what issues they might need to manage.

Another key reason that interviewers ask tough questions: they need to assess your ability to handle difficult situations and produce good outcomes. The true value of an employee is not demonstrated when things are going well; it’s revealed when they are faced with adversity. And many important job skills—such as creativity, problem-solving, social skills, flexibility, persistence, and resilience— are best proven in times of crisis.

A third reason for the tough questions: people learn much more from failures than from successes. Failures are inevitable whenever we are trying new things; they’re normal occurrences when individuals and organizations take reasonable risks. What’s important about failures is that their consequences are limited, and that they produce learning that generates better outcomes later.

(Note that attempting to avoid all risks is a form of failure itself. Companies that don’t take risks may find their markets stolen by scrappy competitors. Investors who put all their money into “safe” instruments like savings accounts, CDs, and bonds are taking less investment risk than stock market investors, but are likely to experience devaluation of their assets over time due to inflation.)

Ground Yourself in Reality: Nobody’s Perfect

The pressure of interviewing can make you set unrealistically high expectations of yourself, and to suppress anything that might make you look imperfect. This can be counter-productive; it can increase anxiety (“what if they find a flaw?”), and leave you unprepared to talk realistically about challenges you’ve faced and how you have dealt with them, which is what most interviewers want to know.

Most interviewers don’t expect perfection; they understand that every candidate is an imperfect human who has some “dirty laundry”. They simply need to understand the nature of any issues, how big they are, and what impacts they might have. If you can’t discuss them openly and honestly, you can leave the interviewer very unsatisfied, and thinking thoughts like:

• “This candidate isn’t being honest with me.”
• “This candidate thinks (s)he’s God’s gift to the world!”
• “This candidate has no self-awareness.”
• “This candidate is too cautious, and unwilling to take reasonable risks.”
• “What issues will I learn about only later?”

As a candidate, you need to provide the interviewer enough information to convince them that you’re real, that you’re aware of your limitations, and that the positives about you greatly outweigh the negatives. Getting more comfortable with talking about your imperfections can greatly increase your confidence in interview situations, and make you a much more attractive candidate.

Tough Questions that Often Come Up in Interviews

To prepare to respond to tough questions, you must first anticipate which ones are likely to come up. Start by thinking like the interviewer – what concerns should they have about all candidates for the job, and what concerns should they have about you in particular?

Concerns that relate to the nature of the job are often addressed using behavioral interview questions, which seek evidence that candidates have demonstrated skills in actual job situations. Here are some examples:

• Tell me about a time you realized that you would not be able to deliver on all your commitments, and how you managed it.
• Tell me about a time you had a conflict with a co-worker / boss / customer, and how you resolved it.
• Tell me about a time you made a significant error, and what you did to correct it.

For more about behavioral interviewing, see Getting the Most Out of Behavioral Interviews.

Concerns that relate to you specifically are often triggered by what is in or not in your work history:

• Why did you leave your job at employer X?
• Why were you fired?
• Why do you have a significant gap in your work history?
• Why have you changed jobs so frequently?
• Why did you stay at one company so long?
• Why did you make a major change in the type of work you do?
• Why do you want to do this job, when your work history seems very different from it?
• What is your greatest weakness?

Practice Your Responses

After you have created a list of tough questions that are likely to come up, compose responses to them. Keep in mind your primary goal: you want to alleviate concerns that the interviewer might have about how you would perform in the job. To do this effectively, your responses need to be:

Clear, concise, and straightforward

A muddled or incoherent story will only increase concerns. Keep it short and tightly focused.

Stated with confidence

Any apprehension you show in talking about the situation will leave the interviewer also feeling uneasy. Practice the story until you can tell it in a matter-of-fact way.

Demonstrating a forward-looking mindset

Interviewers want to know that you learn from your mistakes, and that you are continuously striving to improve. Look for the lessons in your stories, and finish them by talking about how you have been applying what you learned.

You may find it helpful to practice telling your stories in front of a mirror, or to a friend or coach who can give you feedback.

Some Real-World Examples

To give you a better sense of how the above guidance shapes stories, I’ll share some examples that have been used by candidates I have coached.

• “I had to quit my job as a program manager to take care of my ailing parent, which was itself a full-time job. I kept up with industry developments and completed online courses in order to keep my skills relevant, and I’m eager to get back into the workforce.”
• “I stayed at __ for 16 years because I loved the work, the people, and the company, but it’s no longer a good fit for me because of recent changes in (industry / management / business climate). While I was there, I gained experience in many different roles, and developed skills that have positioned me for success wherever I land next."
• “After a decade in the insurance industry, I decided that my opportunities for growth and advancement were becoming too limited. I’m transitioning to a role in healthcare because its growth prospects are better, and because I’ll be able to develop data science skills that will be applicable across a wide range of industries.”
• “I was fired from my job as a purchasing agent because an insecure co-worker had been spreading lies about my work, and management believed her instead of me. I learned the importance of going beyond just doing my job well without much supervision; I now make sure that I keep management informed of all the good work I do, so that if there are ever any doubts, they’ll discuss them with me before taking any action."

Prepare for Tough Questions, and Have a Great Interview!

I hope that this article has helped you gain a healthier perspective on tough interview questions, and prepare to answer them effectively. Get comfortable with talking openly and honestly about your mistakes, failures, and shortcomings, and skillful at guiding the conversation from those accounts to the skills and learnings you gained from them that will propel you forward. You’ll project confidence, win the trust of your interviewer, and increase the likelihood that you’ll convert the interview to an offer.

Jim Schibler leads product management teams that deliver software experiences customers love, and he coaches professionals on job search and career management. He writes on a broad range of topics; see more of his articles at his website.

Copyright ? 2022 Jim Schibler — All rights reserved

Image Credits: Torturer courtesy Bethesda Game Studios; Mistakes courtesy Despair.com; Laundry Basket (creator unknown); Interviewing Candidate courtesy Edmond Dantés at pexels.com; Mirror Practice courtesy tschundler at flickr.com.