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“Tell Me About a Time You Failed”: How to Answer Like a Pro

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We’ve all been there—you’re in a job interview, on a date, or at a social gathering, and you’re asked that dreaded question: “Tell me about a time you failed.”

It’s a question that often leads to cringe-worthy moments or awkward silences.

But what if I told you that there’s a tried-and-true formula for answering this challenging question? Let’s dig into how to tactfully share a story about failure while emphasizing your growth and resilience.

Watch our video below to learn the power of sharing failure:

Answer With Your True Failure and a Redemption Story

When faced with the question about failure, your best bet is to share a genuine, heartfelt experience. Don’t try to mask it or make up a story; people can sniff out a lie. Honesty, especially in admitting faults or shortcomings, is generally appreciated and can even make you more likable.

But we need an “aha!” moment for this failure. This is where the redemption part comes in—what did you learn? How did you grow? And how did this failure make you a better person?

Remember this formula:

True Story + Redemption = Success

Like this:

“In [Year/Timeframe], I was working on [Project/Task] at [Company/Occasion]. Despite our best efforts, [Specific Failure]. This led to [Impact/Consequence]. However, I took it as a learning opportunity and [What You Did to Redeem Yourself].”

Here’s the formula, broken down into bite-sized tips:

Choose a failure story

The first step is selecting a failure that is both real and impactful enough to share. Remember, everyone has failed at some point, so admitting to a mistake can actually make you more relatable.

If you’re struggling to think of something, keep in mind these 4 points:

  • Relevance: Your failure should be relevant—for example, if you’re in a job interview for a marketing position, a failure related to a marketing campaign would be more relevant than, say, forgetting your friend’s birthday.
  • Impact: Choose a failure that had a real consequence, such as missing a deadline and losing out on a potential client.
  • Learning Opportunity: Your failure should ideally be something that spurred personal or professional growth. Did it make you reassess your priorities? Did it result in you acquiring new skills? Or perhaps you decided to delve into a great professional people skills gift:
pointing in photos

Master Your People Skills

  • Create a Memorable Presence
  • Communicate with Confidence
  • Achieve Your Goals

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  • Recency: While a failure from your distant past could still be relevant, something more recent may be more convincing as it shows your ability to adapt and learn in your current stage of life or career.

Be specific

Sure, it might feel better to be less vulnerable and hide those iffy parts of your failure story.

But vague or generic answers don’t impress anyone. So be specific.

What happened? Who was involved? What was the outcome? Specific stories are much more engaging and believable.

Take these two stories, for example, and notice how much better the specific story is:

Vague: “Yeah, there was a project that didn’t meet its goals because of some delays and miscommunication. We tried to make it work, but it just didn’t. However, we learned from it, and future projects were more successful.”

Specific: “Two years ago, I was leading a team of five on a software development project for a key client. Our goal was to launch a new feature for their website within three months. We were well into the second month when one of our main developers had to take an emergency leave, and the ripple effect led to delays in two critical stages of the project.”

Aim for less than a minute

Aim to share your story in about 30 seconds to a minute. Dwelling too long on your shortcomings could create discomfort or cast a shadow over your capabilities.

Too short, on the other hand, and you risk treading on vague territory and not going deep enough.

Highlight your redemption

This is perhaps the most crucial part. After you share the failure, immediately follow it up with what you learned from it, how you grew, and how you remedied the situation.

People love a good comeback story!

The Structured Approach (Formula)

To craft an answer that leaves an impression, follow this simple four-part formula:

Set the Scene: Briefly outline the situation where the failure occurred.

Describe the Failure: Explain what specifically went wrong.

Share the Impact: Talk about the consequences of this failure.

Highlight Redemption: Most importantly, describe how you learned or grew from this experience.

Here’s how to put it together:

“In [Year/Timeframe], I was working on [Project/Task] at [Company/Occasion]. Despite our best efforts, [Specific Failure]. This led to [Impact/Consequence]. However, I took it as a learning opportunity and [What You Did to Redeem Yourself].”

Examples for different scenarios

For a Job Interview

Scenario: You’re applying for a role as a project manager.

Example Script:

“In 2021, I was leading a team to roll out a new software feature at XYZ Corp. Despite our planning, we underestimated the complexity and missed the deadline by two weeks. This led to a delay in the product launch and a loss of about 5% in projected revenue for that quarter. However, I took this failure to heart and enrolled in a project management course. I also implemented new project tracking tools, and since then, my projects have always been on time and within budget.”

For a Date

Scenario: You’re on a date and the topic of personal growth comes up.

Example Script:

“Last year, I planned a surprise weekend getaway for my partner’s birthday. I was so caught up in the surprise element that I forgot to check if they were free that weekend. It turned out they had important family commitments. I felt terrible about it. But, I’ve since learned to always communicate better and consider other people’s plans and feelings. It’s made me a more attentive partner.”

For a Social Gathering

Scenario: You’re at a social event and someone asks about your most significant learning experience.

Example Script:

“A couple of years ago, I organized a charity event where I was overly ambitious with our fundraising target. We fell short, only reaching about 60% of our goal, which impacted the charity’s programs for that year. But, I learned the importance of setting achievable goals and better engaging with the community. The following year, we exceeded our fundraising target by 20%.”

So, When Did You Fail?

Let’s face it: the question “Tell me about a time you failed” is not going away. Whether it’s in a job interview, on a date, or during a casual conversation, people are interested in how you handle setbacks—because life is full of them.

But answering with genuine authenticity will get you ahead of the game. When you’re authentic and vulnerable, you’ll become more likable and relatable—as long as you learned from it. Want to learn to be more vulnerable? We got you covered: How To Be More Authentic By Being Yourself: 3 Easy Steps

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