“What Is Your Biggest Regret?”

“What Is Your Biggest Regret?”

How many work-related regrets do you have? As it turns out, it’s fairly common to wish that things had turned out different in your career. Even the millions of people who left their jobs during the Great Resignation in hopes of finding something better are starting to lament their decisions en masse.

But since time machines have yet to be invented, the best way to handle our regrets is to learn from our mistakes and try to do better — both in our jobs and as individuals.

That’s exactly the type of sentiment you’ll want to convey when you’re asked this common interview question: that although mistakes were made, you were able to grow from them and move on.

So, let’s look at the best way to answer “What is your biggest regret?” in 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 inquiry designed to stretch out the interview’s lengths and throw a wrench into the candidate’s gameplan?

It turns out that inquiring 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 recognize missed opportunities.” And with enough confidence in your interviewing abilities, you can ace this part with flying colors!

­Tom Winter, the lead HR tech recruitment advisor and cofounder of DevSkiller, notes that this is a behavioral 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 recognize their own mistakes and their ability to fix things when needed,” Winter explains.

Tips for crafting 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.

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 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 avers. “So, end by stating what the biggest lesson was from 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 won’t 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 that “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 analyze 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 or 22 years.

Example answers

Are you still unsure how to answer this question? It can be a daunting task, especially as you focus on trying to sell your education, experience, skills and overall résumé 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 realized 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 paycheck 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.

What not to say

So far, we’ve looked at the meaning behind this question and some good ways to structure your answer. But apart from the dos, there are some don’ts, too. Here are some things you’ll want to avoid saying:

Final thoughts

The bottom line is: regardless of age or industry, everyone has some career-related regrets. But when we focus on nurturing a growth mindset, shortcomings start to look less like end-of-the-world scenarios and more like opportunities to learn.

Before we close off, here’s a summary of what we discussed in this article:

  • Some interview questions can sound random, but they’re not. They’re carefully chosen for the hiring manager to form a better picture of who you are as a person, in and out the office.
  • Try not to incriminate yourself — or others. Getting into too many details, beating yourself up or making someone else look bad are all things you’ll want to avoid when answering this question.
  • Add a positive spin to the story you choose to share. If you took a risk that didn’t end up working out, for example, let the hiring manager know what you got out of the process and how it helped you grow.

Regrets are as guaranteed as the sun rising and setting. But as long as you’re honest with yourself, they can help you become an even better person, either at your job or outside the office.

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


Originally published in June 2014. Updated by Electra Michaelidou.

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