How to Answer ‘What Is Your Biggest Regret?’

Illustration of a sad man sitting with his hands covering his face

This just might be one of the trickiest questions you’ll be asked in a job interview – and this concise guide will help you craft a powerful response that’s guaranteed to impress the hiring manager!

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How many regrets do you have about your career? As the years go by, many of us look back at our jobs and wish that some things may have turned out differently. Whether it’s taking that promotion that you thought you couldn’t handle or employing a different approach to a critical project, there are so many elements that we wish we could alter. If only time machines existed!

That said, after several years in the workforce, we all can say: been there and done that. Of course, it’s all about learning from our mistakes and trying to be better – both in our jobs and as individuals.

Because many of us have unique experiences and various perspectives, one of the more common questions that employers ask their applicants during interviews for a position is ‘What is your biggest regret?’. Suffice it to say, for those who have been working professionals for many years, your answer might be the length of a Charles Dickens novel. On the other hand, for those just entering the workforce, your response may be brief, like the length of an EE Cummings poem.

Are you interested in learning more? We’ve compiled an in-depth guide on everything you need to know about this question and what happens in a job interview.

See also: Tips to Prepare for a Job Interview

Why hiring managers ask this question

If you’re applying for a coding position or a sales job, it might seem irrelevant for the hiring manager to learn about candidates’ regrets. Does it serve a purpose and complete a strategy to gauge if you’re great for the position? Or is it a superfluous enquiry designed to stretch out the interview’s lengths and throw a wrench into the candidate’s gameplan?

It turns out that enquiring about applicants’ regrets is part of determining if the applicants can engage in self-reflection and initiate fundamental analysis of their past decisions and choices, says Irene McConnell, the managing director of Arielle Executive. ‘This gives a good understanding about the interviewee’s resilience and ability to recognise missed opportunities.’ And with enough confidence in your interviewing abilities, you can ace this part with flying colours!

Tom Winter, the lead HR tech recruitment advisor and cofounder of DevSkiller, notes that this is a behavioural question, allowing the interviewer to get to know you and your personality, thought processes and approaches to day-to-day challenges. ‘This question is specifically designed to understand how the person reacts to negative emotions, their ability to recognise their own mistakes and their ability to fix things when needed,’ Winter explains.

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How to craft a response

Now that you’re aware of the why, let’s get familiar with the how. In other words, how do you provide the best answer to this interview question? According to industry experts, the best reply is honest, thoughtful, introspective and solution-based, without any hint of negativity or resentment.

Let’s dive into some of the best tips for devising a stellar answer:

1. Don’t get personal

Yes, we all have regrets in our personal lives. The one who got away (or the one who stayed). The friends we mistreated. The live event we skipped because we didn’t feel like going out on a beautiful sunny day. But while these are universal regrets, they’re not associated with your profession.

‘When answering this question, don’t go into talking about your family, relationships or other very personal topics,’ notes McConnell.

Simply put: when you’re telling the hiring manager about your regrets, be sure to stick to your career rather than your love life. While potential employers do care about the wellbeing of their employees, they’re more focused on determining if applicants and their relevant skills are suitable for the position being offered.

2. Focus on the positive

When you look back at your regrets, it’s important to maintain an upbeat attitude without showcasing an ounce of antipathy for your previous company or your former employer. 

‘It is important to frame this in a manner that shows an ability to grasp reality, learn from it and use it as an opportunity for improvement,’ explains Joe Flanagan, senior employment advisor at VelvetJobs. ‘So, end by stating what the biggest lesson from the said regret and how it has helped in making better decisions.’

This is the most positive spin you could place on your professional regrets, highlighting how you have moved on from it and became a better employee. It’s better than complaining about factors outside of your control without claiming even a modicum of responsibility for what occurred.

3. Don’t play the blame game

One of the worst things every interviewee can do is blame others. Even if you think you’re entirely justified and that it really was somebody else who was in the wrong, it’s best to refrain from passing the buck. Instead, it’s about owning your mistakes, inspecting the past and moving on knowing that you have learned something, says Flanagan.

‘Candidates should not blame external factors, like a boss or a colleague, for their decisions, [and should] instead focus on their own role, learning and progress,’ he averred. ‘So, end by stating what the biggest lesson was from the said regret and how it has helped in making better decisions.’

By doing this, you’re placing an emphasis on your maturity and how serious you take your growth in your professional life and personal development.

4. Choose a regret that won’t disqualify you

How do you know choosing a regret to share with the hiring manager will not disqualify you from the position? This can be a challenge because you’re not a mind reader, and you desire to be forthright and open about career regrets. Indeed, you might think that potentially revealing weaknesses could diminish your odds of being accepted for a position.

Alex Mastin, the founder and CEO at Homegrounds, says that everyone makes mistakes, but it’s crucial that the applicants ‘avoid explaining that they let it still get to them’, adding a growth-based resolution is what interviewers are looking for.

‘What I want to know as an employer is how the potential employee will move past that mistake and learn from it,’ Mastin continues. ‘What I want to know in their answer is how their mistake [affected] them and what tools they used to really grow from it, how […] they [solved] that issue for themselves in order to grow and get themselves back on track.’

Ultimately, Mastin says, ‘mistakes need to be fixed fairly quickly before moving on and letting go; otherwise, it can bring all different parts of the job and the business to a standstill’.

5. Don’t say you don’t have any regrets

Do you think trying to convince the employer that you don’t possess any regrets will increase the odds of being accepted for the job? Not at all. Let’s be honest: nobody’s perfect. By not having any regrets suggests that you’re not growing or maturing, says Flanagan.

‘An outright denial might indicate a lack of maturity or inability to analyse nuanced decisions,’ he points out. ‘More so, this question is usually asked to get the candidate’s perspective on their own choices and journey and, in the process, determine what’s important for them.’

Of course, it might be challenging for any prospect to answer this question on the spot. But now you can overcome it and think about what could be your biggest regret in your career, whether it spans 2 years or 22 years.

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Example answers

Are you still unsure how to answer the question? It can be a daunting task, especially as you focus on trying to sell your education, experience, skills and overall CV to the employer or hiring manager. But don’t worry! We have some examples of what to tell the company about your regrets and ensure you have a successful interview.

1. When you turned down a job

‘There was a position that I could have gotten. It was really up my alley, but I rejected the offer. It was foolish on my part. I was not confident in my abilities, but as the years have gone on, I’ve learned that I should be a bit more confident because I’m a fast learner and I’m easily adaptable.’

2. When you didn’t land a client project

‘Years ago, when I was working at a mid-cap firm, I felt horrible because I failed to land a client project. This was extremely disappointing to me, and I felt like I let down the entire business. People tried to reassure me that it was a team effort and that it was not exclusively my fault, which I never believed. It was one of the reasons why I left. Looking back, I realised I was in the wrong. First, you shouldn’t take your ball and go home. You learn from your mistakes and determine what went wrong. Second, companies are a team effort, so it helped me be more trusting of my colleagues and, eventually, persevere.’

3. When you didn’t follow your dream

‘I was always of the mindset that you should take a job that will offer the highest salary. Since I know what it was like to starve, I wanted the biggest paycheque possible. This, unfortunately, forced me to miss out on incredible opportunities that would have allowed me to see some of my dreams, even though the pay was a little bit lower. Since then, I’ve learned to do a balancing act of maintaining my professional growth but also dabbling into my dream work on the side.’

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Final thoughts

What is your biggest regret in your career up to this point? Everyone has them, sometimes on a weekly basis. While you may have manufactured a blueprint of your working life, not everything may have gone according to plan. This doesn’t mean your professional life has been a failure. In fact, according to many experts, these are instances where your integrity is tested, your character is challenged and your overall aptitude allows you to make a major day-to-day decision.

Regrets are as guaranteed as the sun rising and setting. It’s about how you grow from past mistakes and develop better solutions for the future. As long as you’re honest with yourself, you can become an even better person, either at your job or outside the office.

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Join the conversation! Has this question ever come up in an interview before? Share your thoughts and experiences with us in the comments section below!


This article is an updated version of an earlier article published in June 2014.