Interview Lesson 101: What is your biggest failure in your career in finance?


As interview questions go, this one is second to ‘what is your greatest weakness’ in the list of feared questions. It may send you running to the hills when you think about it now, but it’s actually a great one to answer. And the perfect opportunity to show your strengths as an emerging finance leader.

Answer the question directly, don’t try to avoid it

I’ve asked this one a lot over my career, and 8 times out of 10, someone will provide an answer that pivots on something that ‘could’ have been a failure, but they managed to turn it around at the end OR it turned out it wasn’t that ‘bad’ after all.

This isn’t the question. The question is about a failure, not a semi-failure, or nearly-failure. And it’s not a question about problem solving or turnaround.

Think of something from earlier in your career you’ve really learnt from

Everyone has an early people leadership mistake. Or an example of a conversation with a stakeholder/customer/vendor/partner/non-finance manager that didn’t get the outcome you needed it to. Of course, you don’t want to showcase something that is really bad, so sense check your example for anything that might question your skills in finance or business.

Play this example out stage by stage, what went wrong? And how did you learn from it?


Explain how this has shaped you as a leader now

Talk the interviewer through how you’ve used that learning to shape your leadership or engagement/communication style now. Show clearly that you understand why this situation failed and what you could have done to make it succeed.

To really reinforce this point, think of a time more recently where you’ve been in a similar situation, but turned it into a success. Explain how you applied your learning, and how this engineered the successful outcome.
Above all, don’t equate failure with weakness. Everyone makes mistakes, and in many people’s view, it’s the only way you learn. Bear in mind that many businesses want people who are resilient and tough, and in the majority, these people have been through failure to make them that way. Moreover, you don’t want to come across as ‘perfect’, as this could communicate a lack of self awareness and emotional intelligence and worse still, may be perceived as a potential barrier to continued development as a leader.

Admit your failures, but critically, show that you don’t make mistakes twice!

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