Master 30 tough interview questions covering pressure scenarios, ethical dilemmas, and high-stakes decision-making.
Question 12 of 30
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Christine Pasqueretta is a human resource and recruitment professional with experience creating, developing, implementing, leading, and measuring HR impact initiatives.
Think about a time you failed, or made a big mistake. What would you change about that situation, if you have an opportunity for a re-do? Perhaps there is a missed opportunity that you still regret not taking. This question sounds more intimidating than it is. Even though the interviewer is asking about your most significant regret, you indeed don't have to share the worst mistake you have ever made in your life. Make sure that you keep your answer professional and career-related.

Christine Pasqueretta is a human resource and recruitment professional with experience creating, developing, implementing, leading, and measuring HR impact initiatives.
"I had an opportunity to study under one of the top personal trainers in the country, but I was so busy with my clients that I didn't take the chance. Looking back, I know I could have learned so much from them. Now I pay much closer attention to educational or training opportunities that come my way."

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.
"I am of the belief that it live is meant to be lived without regrets. Does that mean you don't fail or learn from mistakes? Not at all. We all make choices in life, and we should embrace them, and adapt when we want to change course. JK Rowling has a great quote that comes to mind when asked about regrets. She says, 'Some failure in life is inevitable. It is impossible to live without failing at something unless you live so cautiously that you might as well not have lived at all"”in which case, you fail by default.' That sums out how I feel about failure and regrets."

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.
"The most prominent regret I have is with my most recent career move. Despite doing my due diligence, and working with an experienced headhunter, the role was not what it was supposed to be, and the company was in complete disarray. Despite this misstep, I did learn a lot over the past year. I stuck it out, adapted to the changes, and have made the best of it, despite the bait-and-switch and multiple leadership changes. I honestly don't know what I could have done differently, besides not taking the position. Because of that, I feel that it was put in my path as a learning moment and to test my resilience. I feel as though I've passed the test and it is time for the next opportunity."

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.
"The most significant regret I have would be not advocating for myself early on in my career. I believe I was passed up for two promotions that I deserved because I was too concerned with being friendly and likable. I missed out on opportunities to advocate how I was the best for the position because I didn't want to ruffle any feathers or be unlikable. Luckily, I've learned quite a bit since, and I've earned plenty of promotions since, however, I sometimes wonder where my career might be if I would have received those promotions early on. Nevertheless, I know I've learned plenty from those experiences of being passed over."

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.
"I feel pretty fortunate that I don't have many regrets, but I'd say the one that would nag at me most would be that I didn't leap into marketing sooner. I think my career would be on an even better trajectory if I'd jumped about six months earlier. However, I am where I am today because of the decisions I made, and I feel great about where I am today and the prospect of working here!"

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.
"My biggest career-related regret is my choice to enter the private school sector before entering the public school sector. I found a home, and a new passion for teaching, once I began working in the public school system. I wish I had chosen this path all along!"

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.
"I do not believe in living life with regrets; however, if there is one thing I could change about my career path, I would have completed my business administration degree before entering the workforce. It's ten times as tough to complete my education now that I am taking online courses on the weekends! I do look forward to finishing what I started, though! My estimated completion date is this April."

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Anonymous Answer
I had a JCAPHO class I could of went to for extra credits for the Eye clinic. I missed it due to being so busy at work. I want to try to go to more of these classes when they become available to build my skills and keep learning.

Rachelle's Feedback
It's great that you recognize the importance of attending these classes, which will help get you to your end goal!
Anonymous Answer
My biggest regret is that when I was running my own consultancy, I focused my attention on execution and none on marketing and networking. As a result, when the main client merged with their biggest competitor, I lost most of my business. The biggest takeaway from this is that if I ever do this again, I need to spend some of my week, say 15 %, on marketing, writing blogs, and networking with clients.

Rachelle's Feedback
It sounds like a lesson to learn, indeed! One suggestion is to avoid mentioning going out on your own again, as this could have the interviewer feeling that you would not stay long-term if hired. I have offered a slight revision below.
My biggest regret is the way that I set up my business when running my consultancy. I focused all of my attention on execution and put little emphasis on marketing and networking. As a result, when my main client merged with their biggest competitor, I lost most of my business. The biggest takeaway for me is that every business should dedicate a percentage of their time to marketing efforts such as distributing digital content and networking with prospects and clients.
Anonymous Answer
My biggest regret is not completing college before entering the workforce. Competition is tough to beat with taking only part-time, weekend, and night classes. I do look forward to finishing what I started, acquiring my bachelor's degree, to moving up to a senior or supervisor position.
Marcie's Feedback
This is a strong answer because while your regret is legitimate, you explain your desire to one day overcome it by obtaining your degree. Perhaps talk a bit about why you didn't finish college so the interviewer understands what happened. And definitely emphasize any plans you have to take additional courses in pursuit of getting your degree in the future.
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Written by Rachelle Enns
30 Questions & Answers • tough

By Rachelle

By Rachelle