How to Answer Tough Interview Questions Like a Pro

It’s easy to spiral when you’re asked a hardball question in a job interview. These hiring experts share tips on how to get back on track after a tough interview question.

Written by Sunny Betz
How to Answer Tough Interview Questions Like a Pro
Image: Shutterstock / Built In
Matthew Urwin | Jan 31, 2024

Even the most experienced professionals can get tripped up by tough job interview questions. That’s why we’ve compiled a list of the most common and challenging interview questions — and sample responses for how you can answer them.


Tough Interview Questions and Sample Answers 

Interviewers may ask tough interview questions to go beyond your resume and get a deeper understanding of your skill set and professional background. Here are some questions you might be asked along with sample answers, so you can set yourself apart as a top candidate.

1. Tell Me About Yourself

This question often comes up in the early rounds of the interview process. While it’s intentionally open-ended, your answer should still focus on your professional experiences and skills that are most relevant to the role you’re applying for. Be sure to note a few strengths and accomplishments that confirm your fit for the role. 

Example: “After earning my degree, I worked for two years as an associate product manager before being promoted to my current role as a product manager. During this time, I have overseen 12 successful software releases over the past three years while leading collaborative efforts between the product, engineering and UX design teams. On top of this, I’ve worked to cut the product development process in half, and I’m eager to achieve this same kind of efficiency at your company.”  


2. When Is a Time You Received Critical Feedback?

Interviewers ask this question as a way to see whether you can demonstrate active listening when receiving feedback. This means not only acknowledging constructive criticism, but responding to it by making an effort to improve your skill set based on this feedback.  

Example: “While I excel at working independently, I’ve been told this working style can result in me being disconnected and hard to work with during team projects. In response, I’ve made sure to ask my peers more questions and share more of my thoughts during team meetings. I’ve also scheduled one-on-ones with each of my teammates to build stronger relationships moving forward.”   


3. What’s Your Biggest Weakness? 

Because not everyone has had a crucial weakness pointed out to them before, this question is meant to test a candidate’s self-awareness. It’s best to provide an honest assessment while outlining actions you’ve taken to improve upon any key flaws. This approach shows you’re willing to hold yourself accountable and take steps to mature as a professional.   

“Showing that you have a growth mindset is more beneficial to an interviewer than just listing your weaknesses,”  Sophie Symonds, senior recruiter at Springboard, told Built In. “Talking about opportunities for improvement can show a company that you’re a self-reflective person with a growth mindset.”

Example: “I used to sometimes struggle with accepting and implementing feedback. To get better at this, I’ve committed to practicing active listening techniques and understanding that my manager’s comments are about improving my writing, not questioning my abilities. I’ve also requested to meet at least once a week with my manager to discuss any questions I have and talk through any concerns to avoid misunderstandings and make sure we’re on the same page.” 


4. What’s Your Greatest Achievement?  

Employers ask this question to get a better sense of what matters to a job candidate. Daniel Miller, head of product at RecruiterPM and co-founder of Empowered Staffing, said that bringing concrete data points to the conversation is crucial in showing prospective employers the value someone brings to their company. It’s more impactful to share something specific, like ROI or the percentage of YoY growth, he said.

Example: “As a sales representative, I’m proud of closing the three biggest deals for my company last year, earning up to $1 million in revenue for the company and contributing to a 116-percent increase in business growth. I’ve since been assigned to three more major clients, showing that my manager now trusts me to secure our business’ most important deals. Achieving such a big win for the company while earning the respect of my teammates has been the highlight of my career.”   


5. Why Should We Hire You?

While this question gives candidates a chance to highlight their best attributes, answers should still be grounded in bringing value to the employer. Candidates who ace this question talk about their strengths and how these will enable them to make an immediate impact at the company they’re applying to. 

Example: “In my current role, I’ve developed a knack for solving complex challenges and making processes as efficient as possible. For example, I oversaw and reorganized workflows for our logistics team, reducing the time it took to complete an order by 60 percent and doubling our production numbers as a result. I will bring this same drive for optimizing processes to your company and look forward to applying these skills in a new operations manager role.”   


6. How Do You Handle Stress?

Many employers value resiliency and adaptability, especially in ever-changing environments and industries. When responding to this question, think of a situation where you faced pressure from deadlines, difficult projects or other challenging scenarios and how you navigated the situation using a positive mindset.

Example: “During busy times, I like to talk things over with my manager. For example, when I had several major projects on my plate, I met with my manager and asked him what projects I should prioritize and what timelines to establish. I then organized my schedule accordingly and completed each project by its corresponding deadline. Maintaining open lines of communication really helps me calm down and understand how to structure my days when I have a heavy workload.”     


7. What Have Been Your Most Positive and Negative Management Experiences?

This is an opportunity for candidates to emphasize what management style they prefer. However, this is not a space for candidates to complain about bad managers they’ve had in the past. Be clear about what behaviors you welcome from managers while remaining professional when talking about managers who have fallen short of expectations.

Example: “I really appreciate managers who remain available for questions, but also know when to let employees solve problems on their own. For example, my current manager lets me schedule quiet time to focus on my work, but I know I can reach out to her via Slack with questions or bring up other issues in our weekly one-on-ones. I had a past manager who was very kind and resourceful, but sometimes they would get a little too hands-on and prevent our team from experimenting with new approaches.”   


8. Why Are You Leaving Your Current Position? 

Companies may ask this question to reaffirm that a candidate is a good fit for the position and to make sure the candidate isn’t simply running away from a less-than-ideal situation. Even if you are ready to leave your job, be sure to place a positive spin on your answer and reaffirm what’s drawing you to apply for a role. 

Example: “While I owe a lot of my professional growth to my current team, I feel I’ve accomplished everything I’ve wanted to in my role and want to take the next step in expanding my skill set and experience as a software engineer, and I don’t think my current employer can offer me this. I was really impressed by the career development plan you’ve laid out for your position, so I feel your company is a place where I can continue down the engineering path I’m passionate about.”   


9. Tell Me About a Time You Overcame an Obstacle

Rarely do things go according to plan in any position, so employers want to know how candidates deal with adversity and how they adjust on the fly. The formula for answering this question should include a summary of the problem, what actions a candidate took and how their actions led to a resolution. 

Example: “In my current role as a marketing manager, I discovered sales reps weren’t using our marketing team’s branding guidelines to describe a new product. To bridge this disconnect, I arranged a joint meeting between our marketing and sales teams to ensure everyone was on the same page. As a result, we agreed to hold these joint meetings once a month, and our customer conversions rose by 40 percent since leads were receiving clear and consistent information about the product.”  


10. Why Do You Want to Work Here?

Employers want to make sure candidates have thought through their decisions and aren’t just randomly applying to jobs. This is also a chance to point out what you like about the company and how you see yourself seamlessly sliding into the company culture. Be sure to draw these connections in your response. 

Example: “I was really impressed with how your company culture encourages cross-team collaboration. As an engineer, I would be eager to work with members on the product and marketing teams to better understand your company’s technology and how it benefits your customers. I also saw you recently expanded into the solar energy sector with your latest product, and I feel energized at the thought of building products that leave a positive impact on people and the environment.”  


How to Answer Tough Interview Questions

No matter what tough interview questions come up, these tips from recruiters will give you the tools to approach your next interview with confidence and ease.

How to Answer Tough Interview Questions

  • Understand your own strengths 
  • Turn your weaknesses into opportunities
  • Take your time before answering
  • Ask tough questions back 
  • Follow up post-interview 
  • Utilize your network


1. Understand Your Own Strengths

When asked what ways people can prepare for difficult interviews ahead of time, Miller stressed the importance of evaluating your own strong qualities before having the hiring conversation.

“People need to understand their own backgrounds before they get on a call with a hiring manager,” he said. “Think about your accomplishments.”

It can be tempting to talk about big-picture progress, but highlighting your specific efforts can demonstrate how you’d be an asset to the team. “Sometimes you want to be like, ‘my team, my company,’” Miller said. “But what can you do without your team and company? Explain the accomplishments you own as an individual.”

More Interview AdviceAnswering ‘How Would You Describe Yourself?’ 5 Tips and Examples.


2. Turn Your Weaknesses Into Opportunities

It’s likely that you’ll be asked to talk about your weaknesses during the interview — Miller hates this question, but recognizes that it’s one most people will encounter. Often the best way to counter that question is to turn your weaknesses into strengths, or at least chances for growth, he said. 

“That question is a double-edged sword,” Miller said. “You need to show that your weaknesses are things that you need to improve on, but that they aren’t going to affect your chances of getting the opportunity.”

For example, if you tend to be overly detail-focused and independent when working on a project, you can talk about the ways you’re learning to share your ideas and accept feedback from others in order to come up with stronger solutions. Be honest about what areas you need to improve upon, but don’t forget to describe exactly how you plan to carry through on that improvement.


3. Take Your Time Before Answering

When you’re faced with a difficult question, your instinct might be to rush and fill in the silence — but that can lead to a superficial answer. Taking the time to pause and gather your thoughts before answering a difficult question may feel awkward, but will show the interviewer that you’re being intentional.

“I think it’s always OK to tell your interviewer, ‘is it alright if I have a minute to think about that?’ rather than panicking and starting an answer you really don’t have the words for,” Symonds said. “It will definitely make you look better than just diving in and giving an aimless answer.”


4. Ask Tough Questions Back

Preparing detailed questions is beneficial in two ways: It’ll help you figure out if you actually want to work for an employer and it’ll show that you have a genuine interest in the position, Symonds said. Find out about the company retention rate — are people sticking around? If you’re focused on growth, ask what training they offer or what the career path looks like for this role. Ask about the challenges your team is facing or what you’ll be expected to accomplish in the first six months. These questions will “give you a sense of how a company invests in its people,” Symonds said.

Keep the interview in perspective and know that an interview goes both ways. Not all interviews will go perfectly, and if that’s the case, then it’s just more information for you to use in your decision. “If you’re not feeling super positive [after] coming out of it, sometimes it’s not even about you, it’s about the company,” Miller said. “It might not be the right fit.”


5. Follow Up Post-Interview

If an interview didn’t go as you’d hoped, that doesn’t mean you’ve run out of chances to make your case. “If a candidate really feels bad about an interview, what I suggest is writing a really good thank you letter that reiterates why they’re a strong candidate, and how they’re excited to move forward,” Miller said.

Plus, a strong follow-up conversation can give you an added opportunity to share things that might have been missed in person and to further display your interest in the company, Miller said. A follow-up note can be the secret key to ensuring managers feel more confident in hiring you.


6. Utilize Your Network

What does networking have to do with answering hard interview questions? Tackling a daunting interview is much easier when you aren’t starting from square one. Relying on your professional connections for introductions and referrals establishes credibility with the hiring manager. It lays the groundwork so that you can better handle those challenging questions.

“Knowing people and building relationships with people so that they will want to help you is part of the interview process as well,” Symonds said. “It always helps if you know somebody that can speak highly of you.”

But what if you’re brand new to the tech scene, and don’t have connections to people at the companies or startups you want to join? Regardless of where you are in your career, you likely already have a network of people to help you along, Symonds said. If you don’t have a robust network yet, start by sending emails to people you admire and ask them about how you could break into the tech industry. 

“I spent a lot of time in college building my network,” Symonds said. “You’re never too young to start building connections, going to workshops and conferences, and introducing yourself.”


Frequently Asked Questions

Some examples of tough interview questions include, “Tell me about yourself,” “What’s your biggest weakness?” and “Why should we hire you?” 

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