How to Answer "Tell Me About a Time When..." Interview Questions

You’ve reviewed your resume, practiced your elevator pitch, and reviewed a few stories you can share during the interview. All is well, and you’re feeling confident. And when the interviewer says, “Tell me about a time you disagreed with your supervisor,” you are ready to go and launch straight into a story about that one time you bravely confronted the director of marketing at your previous company about a new campaign you had a bad feeling about.

Okay, so maybe that doesn’t sound like you—yet. Let’s take a step back and talk about how you can get there.

Pick the Right Story

All these “Tell me about a time when…” questions require stories. As a hiring manager, it’s incredibly unsatisfying to interview someone who has no stories to share. After all, how can someone know what you can do if you can’t talk about what you’ve done? Don’t be that job candidate.

So, how do you find the right stories to share? Go through the job description and highlight all the soft skills that are featured. You’ll likely find things like “ability to work on a team and independently,” “comfort with multitasking,” or “strong communication skills.” Then, come up with an example of a time you demonstrated each of these traits—though keep in mind that you don’t necessarily need a different example for each. In fact, it’s better to come up with stories that are flexible, since you’ll likely have to adapt them to the exact questions anyway.

There are, of course, a few things that interviewers frequently like to ask about that will not be on the job descriptions. Be prepared for “negative” questions, like “Tell me about a time you had to deal with a conflict on your team” or “Tell me about a time you failed.” It’s not that interviewers are out to get you—how you handle conflict and failure are good things to know—it’s just not the best idea to put “must deal with frequent team conflict” in a job description.

Finally, brainstorm a few more questions that could potentially come up based on the position you’re applying for and your particular situation. For example, if you have a big gap on your resume, you’ll want to be prepared to talk about why you’re no longer at your previous job, or if you’re coming into a newly merged department, you should be prepared to discuss a time you’ve been part of a big change.

Make a Statement

Once you have your stories, it’s time to think a little deeper about why these questions are asked in the first place. What does the interviewer actually want to know?

Take a few seconds to think about this before you start answering the question—even if you have the perfect story prepared—so that you can make an appropriate introductory statement about essentially what the moral of your story is going to be. The reason for this is that even though the interviewer is specifically asking you to tell a story, the idea is that he or she will learn something about the way you do things. The problem with this is that what the interviewer gleans from your story could be very different from what you were hoping to share.

For example, say you tell that story about standing up to the director of marketing when asked to talk about conflict with a previous supervisor. You eloquently move through the story about how you shared your hesitation about the new marketing campaign to no avail, but once the initial numbers came in, it was clear that you were right. You triumphantly showed the performance to the director, and she agreed to scrap the campaign. While this story is definitely suitable, there are actually a few different ways it could be taken the wrong way. The interviewer could hone in on the fact that you really didn’t do anything until it was too late or that you were unpersuasive or a poor communicator the first time you raised concerns about the campaign.

To make sure your stories are as effective as possible, make a statement before you start telling the story. In this particular example, it might be something like this, “I learned early on in my professional career that it’s fine to disagree if you can back up your hunches with data.” Now, when you tell your story, it’s not about the various ways you could have approached the situation better, but about how you learned from that experience and how you use it to inform future disagreements.

Finish Strong

So, when it comes to these behavioral questions, have some stories prepared and then practice framing them based on the question you’re asked. Practice, practice, practice, and you’ll sound like a natural in no time. The final piece of the puzzle is wrapping up your answers well. You don’t want to ruin your perfect frame and story by ending your response with, “And… yeah.”

Instead, try connecting the story back to the company or position. Quickly explaining how your experience would be useful in the position you’re interviewing for is always a strong way to wrap up. Another way to finish up a response is to give the “in short” version of the answer. For example, “In short, it’s not that I’m an amazing multitasker—I just set and review my priorities frequently.” Wrapping up an interview answer is such a commonly neglected area of preparation, but it can really help you nail the “strong communicator” impression, so don’t disregard it when you’re practicing.

The thing people assume about these questions is that they’re all about the story. And, yes, that is a critical component. But even if your story isn’t exactly what the interview question asked for, if it’s framed well and you go the extra mile to tell the interviewer what he or she should take away from it, you’ll actually end up making a stronger impression.

So, don’t stress too much about having the perfect stories lined up or the exact relevant experience. Instead, focus on the messages you’re trying to communicate to the hiring manager, and back them up with the stories that you have.

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