How to Answer the ‘Failure’ and ‘Success’ Interview Questions

Published: Jul 15, 2021

 Interviewing       Job Search       
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When you tell compelling stories in interviews, you create connections with your interviewers in ways that just listing your accomplishments (no matter how extraordinary) can never do. Stories connect people to each other because our brains love to follow stories. Stories engage us nearly automatically, trigger our attention, and stay with us—they’re memorable.

So, to help you create stronger connections during your job search, it’s essential to tell compelling stories in interviews—especially when answering popular questions like “Tell me about a time you demonstrated leadership and achieved success as a result” and “Tell me about a time you failed and what you learned from it.”

Before we get into how exactly to answer those two questions, it’s important to understand how to tell strong stories.

Three essential storytelling tactics

First and foremost, it’s essential to ask yourself how you feel about a story before you decide to share it. Your feeling about your story will largely determine how your listener receives and perceives it. For example, if you’re feeling that a story might sound too braggy, or not be what your interviewers are looking for, or like it contains too much information, then your doubt and uncertainty about the story will impact how you tell it. As a result, this will impact how the interviewer receives your story. So, before you decide to share a story, you want to make sure you’re proud of it, it’s a solid story, and it’s worth sharing.

Second, you want your story to include specific details that your interviewers will not only find interesting but also are applicable to the role you’re applying for. This means your story’s implications will be clear—they’ll highlight experiences you’ve had in the past that will inform your future success. Note, though, that your stories don’t have to be directly related to the role. You could be applying for a completely different role than you’ve had in the past, so your experience might be indirectly related. That’s okay. Just make sure that your story’s message is clear and relevant.

Finally, it’s important that you clearly explain the results of your story and what you learned. That is, you want to connect the essence of your story to the role you’re applying for, explaining how they’re related (even if you think it’s obvious) and how you think about your experiences. Interviewers are always judging candidates on how they process and put into context their past experiences.

Now that you understand the storytelling basics, here are two sample answers, using these storytelling tactics, to two of the most widely asked interview questions.

Q: Tell me about a time you demonstrated leadership and achieved success as a result.

A: A year ago, I was transferred into a new department at work. I was assigned as the new team lead. Before I was introduced, the team was disgruntled and had low morale—the department wasn’t staffed properly and turnover was high. There were a lot of office politics going on, and people were burned out and unhappy.

So, I scheduled one-on-one meetings with each team member to understand their issues and concerns. I wanted each team member to feel heard. I asked them each what they thought I should do next and what the biggest challenges the team were facing. I also asked what they thought was holding the team back.

After meeting with each team member, I followed up with everyone as a group. I’d determined from my meetings that the most important thing to do was take quick action to repair some of the issues that were causing the most stress. These issues included managers emailing and Slacking some team members at all hours of the day, including late at night and on the weekends. It also included scheduling too many meetings during the week, and the meetings lasting far too long.

So, I instilled some new protocols around emailing and Slacking, and shortened meeting times. Just by these small initiatives, the results were impressive. Morale significantly improved after 90 days. It was apparent in the energy of the department. Everyone was in much better spirits and much more productive. From these actions, the department’s turnover rate was brought down from 40 percent to zero. 

I think this example demonstrates the way that I lead to get results. My team still talks about the turnaround sometimes, and I’m proud of this because even though I know there were many ways to turn this around, the actions I took were aligned with how I would have liked someone to manage something like this. I think it’s important for employees to be individually heard even when we can’t act on all their suggestions.

Q: Tell me about a time you failed.

A: Early in my career I made the call to hire someone who, in the end, didn’t work out. I owned up to this mistake, made sure to clearly articulate my mistake, and learned what I could have done better in the interview process.

I learned about the characteristics that set A players apart from B and C players. And I learned to ask the right questions early in the search process to avoid wasting time and resources later. Now, I’m extra careful not to hold back on asking hard questions, both during the interview process and when checking references. Now I look for different things in interviews, such as how someone works in teams and how they deal with critical feedback.

Because of this experience, I became a much better interviewer and can better determine if someone would be a good fit or not. Also, I really appreciate how difficult hiring can be, so I’m happy to elaborate on anything that you’d like to know about me and my candidacy.

A final note

Most people feel comfortable speaking about their achievements and successes, but not so comfortable talking about their failures and mistakes. This is understandable, as people often think that talking about failures and mistakes will highlight their weaknesses. So, they shy away from, thinking that speaking about them might hurt their chances of getting the job. However, speaking about failures and mistakes can have the exact opposite effect—they can highlight your strengths.

Keep in mind that it’s unrealistic to have never made a mistake or failed in the past, and unrealistic that you’ll never make a mistake in the future (also, it’s often thought that if you don’t fail, you’re not really trying hard enough and taking enough risks). So, one of the most important things hiring managers want to know is how candidates handle making mistakes and, more important, how they learn from them. So, taking some time now to think about your failures, what you learned from them, and how you’ll be taking different action will be a valuable asset when it comes time for you to tell compelling stories in your next interview.

Natalie Fisher is best known for helping professionals land their ideal roles and achieve explosive salary growth (even with little experience). If you loved her examples above, she has put together some sample stories in a resource called The Ultimate Guide to Situational Based Interviewing. In it, she includes more than 10 examples of compelling stories. The guide includes fill-in-the-blank templates for you to fill in your own stories, as well as 25 questions you can ask yourself to help you find the stories you want to tell in your next interview. You can get a copy of that here.