“What is your biggest failure?”
I’m sure I’ve been asked this question in interviews before. It’s a common, even clichéd question to be asked.
In my case, there’s one very obvious example from my career history: the fact that I didn’t graduate from clinical training as a doctor. At the time, it was very much a career-defining moment with substantial consequences. In the immediate aftermath, I had to secure a first paid job that fitted my education and experience while also dealing with the personal fallout – the emotional storm of grief and regret over letting down my family, anger at the institutions that I blamed for failing me, and the loss of much of my social circle of medical student friends and colleagues who went on to become junior doctors (now called resident doctors). Keenly aware of the sunk costs invested in my education, my father would ask every now and then how my work was going, usually taking the opportunity to suggest that I look for jobs where I could apply my medical training, simply for the sake of not letting it ‘go to waste’. As my career progressed from market research to data analysis, my parents found it difficult to explain my job as a data analyst to relatives in Malaysia – on one occasion settling for the convenient fiction that I “worked in IT”.
Even after all this time I still have occasional recurring dreams about going back to medical school. While I believe I would stand a very good chance of passing clinical training these days, I wouldn’t relish having to navigate the extremely onerous assessment system for clinical skills that was in place at the clinical school I attended – to avoid failing this aspect of the curriculum, you had to leap on every opportunity to tick one off your list, and get a busy healthcare professional to take time out of their day and sign off on the fact that you’d performed the skill correctly before their very eyes – or the encounters I had with the minority of consultants, usually surgeons, who treated students with open contempt and used ward rounds and clinics as opportunities to belittle and humiliate students they took a dislike to. (Hopefully times have changed.)
One of the silver linings, as a few doctors have mentioned to me afterwards in regards to their own careers, has been that I no longer needed to plan my career around the fierce competition for limited training places in the NHS or the standard stages of a consultant’s professional pathway. I have the freedom to choose from many possible directions, unconstrained by the demands of a career in medicine.
There’s an expectation that one should learn from failure; by reflecting on our experiences, we can draw lessons about what happened and take those into future situations. This is the standard advice given to interview candidates, in which the question about failure becomes an opportunity for the candidate to emphasise qualities such as “courage, determination and resilience”. Often, there will be some valuable lessons to learn, but sometimes failures are of no greater significance – just disappointing experiences that teach us little and simply chip away at our dignity – and sometimes failure has high costs and consequences, as described by a woman from Côte d’Ivoire mentioned in Amelia Hill’s Guardian article on the Museum of Failure, who was angry that the museum approached failure from a position of privilege, while she couldn’t afford to fail when her family depended on her business succeeding in order to avoid poverty.
So I’m not too keen on a hard and fast rule around how we should think about and talk about failure – it very much depends on the circumstances, and I’ve been fortunate to work with recruiters and interviewers that retained an open mind with regard to this kind of thing – such as gaps in a candidate’s career history. Failure shouldn’t be treated as a defining feature of someone’s career or life journey, but as a common human experience that doesn’t necessarily rule out someone for a role.
Further reading
- Amelia Hill, December 2025. The Titanic, Sinclair C5 and Brexit: the Museum of Failure is coming to the UK. https://www.theguardian.com/culture/2025/dec/25/titanic-sinclair-c5-brexit-museum-of-failure-coming-uk. Guardian article about the Museum of Failure exhibition, whose founder, Dr. Samuel West, wants to “reframe failure and show it is a universal and neessary part of innovation and learning… we need to take bold meaningful risks to solve the largest problems of our times, environmental, social, economical.”
- Joel Schwartzberg, January 2023. How to Answer “Tell Me About a Time You Failed” in a Job Interview. https://hbr.org/2023/01/how-to-answer-tell-me-about-a-time-you-failed-in-a-job-interview. Harvard Business Review advice that recommends candidates choose a specific episode that paints the candidate in a positive light, in what seems to me to be a particularly manipulative approach to the interview question. Perhaps it says more about US cultural attitudes to self-promotion…
- Indeed Editorial Team, December 2025. Interview Question: “What is Your Biggest Failure?” https://www.indeed.com/career-advice/interviewing/interview-question-what-is-your-biggest-failure. A short, fairly neutral advice article that recommends a three-step approach: choose a specific failure, share the story, and focus on what was learned.
- Nemo Job, October 2023. How to Answer “What Is Your Biggest Failure?” Interview Question? https://talent500.com/blog/how-to-answer-what-is-your-biggest-failure-interview-question/. “Courage, determination, and resilience in the face of failures represent highly attractive qualities in a candidate.” This advice article emphasises talking about the lessons learned and taking responsibility rather than assigning blame to other people or to external factors.