Life is a journey of risk. If you play it safe, you’ll never going to achieve greatness. And it doesn’t matter if we talk about school, personal life, or your professional career. But it is a big difference to risk everything betting on luck, going against strong odds, and to take a calculated risk, cautiously considering your options, making an informed decision, and eventually doing the best thing for your employer. Because that’s exactly what the big corporate guns expect from you, on any leadership or managerial position. You will have to make decisions, and you will take a risk sometimes. Because you won’t have another option. They want to make sure you’re capable of doing it, without risking everything with some silly bet.

Let’s have a look at 7 sample answers to this tricky scenario-based question. You will find on my list examples from both corporate world and private life, because risk comes in many shapes and forms, and your attitude matters more than anything else for the hiring managers. One or two unconventional answers are also in the selection, and I hope you will find at least one answer that resonates with you, and makes sense for your interview and level of experience. Do not forget to check also my notes below the answers, for additional hints and explanations.


7 sample answers to “Tell me about a time when you took a calculated risk” interview question

  1. I recall such as example from my last managerial job. Leading a small team of developers, we were working on a new game for Android. But we knew that two other competitors were working on a similar release, and it was a race with time. Whoever released the game first would have the biggest chances of acquiring the prime position on the market. We had our insiders information, and I actually knew that we were behind one of the competitors. And I also knew that they had great PR and big marketing budget, and if they released the game before us, it would be game over for our studio. So I decided to skip the beta-testing phase. We just did some quick tests and released the game with the bang, aggressive marketing campaign followed. Of course some bugs appeared, and it was stressful, but I still considered it the best option in the given situation. Because if we did the standard one month testing period the competitor would release the game before us, and we would relinquish the coveted first position. My calculated risk paid off. We got many people hooked, managed to deal with the small bugs, and the company made hundreds of thousands on the release.
  2. I am taking such a calculated risk right now. Because I refused the offer I got from ABC company just two days ago, knowing I have an upcoming interview with you–my dream employer. It is a risk without a doubt, because I got a very decent offer from them, and it is not guaranteed I’d succeed here with you. But I have confidence in my abilities, and believe that my experience and education is an excellent match for this job. So I decided to go all in, instead of playing safe. Still I consider it a calculated risk, because even if you do not hire me (which I hope won’t happen), I can try my chances and ask for another chance with ABC…
  3. I took a calculate risk when applying for a place at a law school. You know, I didn’t want to do ten interviews and trips. I just couldn’t afford it with my busy schedule. So I sent my applications to three schools only, which, most certainly, many people would call risky. But I knew my GPA was good enough, I spent hours doing my research about the schools, and I knew that at all three would almost certainly invite me for an interview. And that’s exactly what happened, they accepted me to two of them, and here I am a few years down the road, applying for a job of a legal associate with you.
  4. I took such a risk in my last job of a logistics manager in a big warehouse. We struggled with staff. The workload was heavy, payment was low, and some people left for better jobs. I needed to replace them, but we didn’t have many candidates for the job. And so I decided to contact a staffing agency and recruit foreigners. It had a lot of risks associated with it–the language barrier, working experience and references that were hard to verify, uncertain response from existing employees, and so on. However, the only option I had was keeping the place understaffed, and increasing the workload for existing clerks, which would result in even more people leaving the place, and the problem widening. I could not afford it to happen. And so I decided to take this calculated risk with the staffing agency and foreign workforce, who didn’t demand wages we’d not be able to pay. Sure enough, there were some issues, and we had problems with the new employees. At the same time, however, I kept the operation going, and managed the workload, which was the most important thing.
  5. To be honest, I am not a man of calculated risk. I always follow my instincts, the gut feeling if you want, polished by years of experience in the field. Telecommunications is not a field where you can afford to wait. If you hesitate and take too long before making a decision, competitors will eat you alive. And you will miss the price entirely. I had to decide quickly always, and I followed my instinct, which proved successful most of the times. Without a doubt I made some mistakes. But if I waited for all analyses to be completed every time, and to have all information I needed to be able to take a highly calculated risk, I would just lose every time. Because one of our competitors would take action before us, and take our market share. That’s the way I see it. But I can assure you that having the luxury of time, I will consider all options carefully, and take calculated risks.
  6. I guess I took a calculated risk in my personal life. Two years ago, an amazing girl chased me. She kept texting me and tried to hang out with me. I knew I could have her, and it was as tempting as you can imagine. But I also knew I was amidst the hardest year at the University, and simultaneously having two part time jobs. I just didn’t have time to pursue a quality relationship with a woman. And so I decided to take a calculated risk, and let it go. Because I believed I could afford it, with my looks, education, and social skills. I knew that a time would come when I had more time. And that’s exactly what happened recently, after I finally graduated and ditched my part time job. I found a girlfriend, a great girl indeed. And at the same time I have a degree in my hands and can pursue this amazing career. Not sure if it would be the same story if I went after the opportunity with the other girl back then, because she was a huge party lover. Now it seems that my risk paid off.
  7. I’ve been an avid poker player for the last eight years. Now it doesn’t mean that I play professionally, or dream of making a living playing the game. Not at all. But I devote a lot of my free time to online poker. And I can tell you that more than anything else, it taught me to take calculated risks. Because if you want to be successful in a long run in poker–and perhaps also in business, you cannot rely on luck. You have to count your odds of winning each and every time, and take the risk–or avoid it, accordingly. I’ve been successful in the game, and believe I can bring the same attitude to my corporate office. Without a doubt, I’ll have to consider different things than I do at a poker table, but the principle remains the same: gauge the odds of winning carefully, and place your bets accordingly…


Doing the best thing for the employer, each and every time

When you aren’t sure how to answer a scenario-based question in your interview, or what attitude you should try to show, you can always remember this one: doing the best thing for the employer. And it is no different with taking risks.

Narrating the situation in an interview, ensure them that the decision you made, the risk you took, was actually the best thing you could do for the prosperity of your employer. Of course, you should be able to elaborate on it, explaining the risks other decisions would posses, and why the action you took made a perfect sense in the given moment. Check sample answers no. 1 and no. 4 from the list for good examples.

At the end of the day your judgment might prove incorrect, and the company might lose some money. But you did what you did with the best of intentions, and that what matters at the end of the day. Because a calculated risk is still a risk, and it won’t pay off each and every time…

* Special Tip: This isn’t the only difficult question you will face while interviewing for any decent job. You will face questions about prioritization, dealing with pressure, dealing with ambiguity, and other tricky scenarios that happen in the workplace. If you want to make sure that you stand out with your answers and outclass your competitors, have a look at our Interview Success Package. Up to 10 premium answers to 31 tricky scenario based questions (+ more) will make your life much easier in the interviews. Thank you for checking it out!

Don not hesitate to use an example from your personal life, or even an unconventional answer

It is easy to pick an example from work when one has ten years of professional experience under their belt. But what if you are just staring your professional career, and didn’t have a chance yet to make any important decisions at work, to take any risks?

In such a case, you should either refer to a situation from your personal life, or opt for a philosophical answer. Answers no. 5, 6, and 7 from my list are interesting examples. And while it may sound counterproductive to talk about playing poker, or about a relationship you let go, while you try to get a job with some corporation, you should remember that corporate managers are also men and women, from flesh and bones.

They also have their hobbies, virtues and vices, their joys and struggles. Talking about a situation from your personal life (while answering this question or any other one), you can actually connect with them on a rather personal level, especially if they have experienced something similar in their lives. So, as long as the example from your personal life conveys the attitude you try to convey, you should go for it!


Alternative question no. 1: What are the biggest risks you have taken in recent years?

In some instances they were ask you about the biggest risks you took (calculated or not), in recent years or overall. As always, your reasoning is the key, because no situation is black and white. As long as you can explain why you took the risk–you didn’t have another option, you saw it as a best thing to do for yourself or your employer, it was worth taking considering the eventual reward, etc, you will be good to go.

As I’ve already said, if you’re just starting your professional career or lack experience, you can talk about risks you’ve taken in relationships, in your personal life. Make sure to show them that you aren’t a coward, and when a situation demands it, you can take a risk, even a big one.


Alternative question no. 2: What was the first risk you ever took?

I’ve seen this question on some job application forms and essays for school admission process, hence decided to include it here. I like it, since it offers a lot of room for creativeness. You can take the question literally, and say that the first steps you tried to take as a child, risking an inevitable fall, was the first risk you ever took. Or further down the road, the first girl/boy you professed loved to, risking rejection and tears

Of course, you can also refer to first risk you took in school or work. Let your creativity roam, and show them that you are a courageous individual. You do not aim for mediocrity or conformity in life. Hence you have to take risks at times, and you do it with gusto!

Ready to answer this one? I hope so! Do not forget to check also 7 sample answers to other tricky interview questions:

Matthew Chulaw
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