What is the riskiest decision you've made in your career?

Why the Interviewer Asks This Question
What You Need to Know
Experienced Example
Community Answers

Risk-taking plays a role in their company culture. One of Facebook's original core values was to "Be Bold." Often, being bold requires taking calculated risks. Mark Zuckerberg also detailed in an address that information flow is necessary for making calculated risks. So, your interviewer is curious about your approach to taking risks, your experience, whether you are risk averse, or whether you compulsively take risks based on intuition rather than information. As one senior Meta employee puts it, part of what makes someone successful at Meta is the ability to make "bold decisions and take calculated risks without being afraid of being wrong."

In one of Meta's interview prep guides, they advise their candidates to be honest. "Not every project is a runaway success. Being transparent in these situations won't be counted against you in the interview. In fact, sharing & discussing how you learned, improved, and grew from your past experiences is valued. Know yourself. Take the time to review your own resume, as your interviewer will almost certainly ask about key events in your work history. Be prepared to discuss projects in depth. It's helpful to outline 2-3 major projects ahead of time." And, as Mark Zuckerberg once said, "The biggest risk is not taking any risk... In a world that is changing really quickly, the only strategy that is guaranteed to fail is not taking risks."

"One of the riskiest decisions I made was to leave my job with an established organization to create a startup. But I did so in stages, first by reducing my hours, from full-time to part-time, then by making the leap to dedicating myself to the business full-time. My start-up was focused on providing a service that would pioneer a new space in the nutraceutical marketplace. Of course, we had some roadblocks along the way, but I learned to quickly pivot in the face of a challenge. I grew significantly during that time, and although it was a risk, I stand behind my choice. I later sold the business and did well, and was incredibly proud of what I created and passed on. It was a lot of work, sometimes too much work, but working hard and putting in long hours is something I am used to."

Anonymous Answer

"One of the riskiest decisions I made was my attempt to transition from the EE side to Computer Software. I have an MS EE background, and I could have stayed in my comfort zone and stuck to working in companies where I could continue to build on my EE background. I chose to leave my comfort zone and take on more challenging roles that needed me to ramp up on the software side. I have done this so many times now, and I have learned and grown from these experiences."

Rachelle's Feedback

Excellent answer! It sounds like you made a well thought, calculated risk and ended up winning. Nice work.

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Anonymous Answer

"The riskiest decision that I took was when I was given an opportunity to lead an infrastructure team outside of my domain area. I had to spend the extra hours and learn about the technology and nuances of it. However, it paid off, and I was very successful at it. Since then, I have taken more responsibilities from different infrastructure towers."

Kristine's Feedback

Nice response! It's a strong start. To help the interviewer understand the impact of this decision, I recommend elaborating by explaining what new technology or technologies you learned as a result of accepting the project and more about the outcome or achievements of the project. I reworded it slightly for clarity.

"The riskiest decision that I took was when I decided to accept an opportunity to lead an infrastructure team outside of my domain area. I spent extra hours learning about the technology and its nuances. However, it paid off, and our team was successful. Since then, I have felt confident in taking on more responsibilities from different infrastructure towers."

Anonymous Answer

"The riskiest decision I ever made was to present something different than what the client asked for. I thought my choice would be better for them. One of the managers from the client-side argued with me because he had promised something different to his CEO; however, once I presented it to the CEO, he liked the idea, and we proceeded with it."

Stephanie's Feedback

This is a great example, but you could improve your response by clarifying just a bit by how you handle potentially risky situations at work. Do you manage risk? Can the hiring team feel confident that you'll take the right risks without creating unnecessary challenges for the company? These are a few questions you may wish to consider.

Anonymous Answer

"One of the riskiest decisions I made was to leave my industry job and join academia to boost my knowledge of database systems. It was very hard, in the beginning, to cope with the coursework, research work, and project works. I worked very hard to balance my time to be as productive as possible in my research. I failed a lot along the way while defining my thesis topic, research goal, and new solutions for my problem. At the same time, I learned how to think critically, understand the state of the art systems and build on small research ideas to complete full-grown systems."

Cindy's Feedback

Good. Can you explain your decision-making process and discuss the pros and cons? The question presents an opportunity to show your reasoning and demonstrate your ability to make logical high-stake judgements.

Anonymous Answer

"I would say when I left xx as I had spent many years of my education and competition to get there. At the time I left without a solid position at hand, but just with the conviction that I wanted to work in a fast-moving company, the technology industry in Southeast Asia. It was a risk, but with just that goal in mind, I worked myself towards it, acquired new skills, got to work in known tech companies in Thailand, got more education in business, and here I am, more solid than before."

Stephanie's Feedback

Wow! Good for you for taking that risk. It can feel daunting to jump out on a limb not knowing what will catch you, but it sounds like you made this decision thoughtfully and the rewards have paid off for you.