What is the Worst Thing That You Have Gotten Away With?

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“What is the worst thing that you have gotten away with?” This is a rare interview question, but some employers ask it in order to get a better sense of your personality and whether you would fit in with the company. An employer might also ask this as a way to make sure you have not done anything that might be considered a red flag for the position.

This is one of those tricky interview questions. You don't want to say that you never did anything that you have gotten away with, because nobody is perfect.

On the other hand, you definitely don't want your "worst thing" to be something really bad, such as something illegal, unethical, or cruel.

What the Interviewer Really Wants to Know

Interviewers who ask trick questions like this one really want to see whether you can “think on your feet” when pressed. Can you maintain your composure even as you navigate between saying too much and saying too little?

Unlike many trick questions, where there may not be a right or wrong answer, you do need to think carefully about the example you choose to share with the interviewer in order to avoid saying something that might be construed negatively.  

How to Answer "What is the Worst Thing That You Have Gotten Away With?”

One way to answer is to keep your response on the light side. For example, you might give an example of something small that you got away with that involves your parents or siblings or school (staying out late, pulling a prank, etc.).

You might also turn the question around and instead provide an example of the “best” thing you got away with. For example, you might explain that you did a good deed for a friend and he or she never found out it was you. However, you don’t want to sound perfect, so you might conclude with a quick, lighthearted example of something more mischievous that you got away with.

Examples of the Best Answers

Here are some sample answers you can use for inspiration as you decide which bit of mischief is “safe” to discuss in your own response.

I’ve never been much of a troublemaker, even as a teenager. I suppose the biggest thing I ever got away with was a college prank I helped organize and arrange. We turned all of the desks upside-down in every classroom. I love to have fun, positive relationships with my colleagues, although I think my pranking days are over!

Why It Works: This answer is expressed light-heartedly, demonstrating that the candidate has a goofy side that might make him a congenial team member. It also shows how he and his friends were able to relieve some college stress by “acting out” in a way that was non-destructive – a useful talent for professionals whose jobs require that they work in fast-paced, high-stress environments.  

While this is actually a positive thing, the biggest thing I got away with was helping to arrange a surprise vacation for a sick friend. We planned the whole thing without her finding out until we took her to the airport! Of course, I’ve gotten away with a couple of less positive things too – I’m sure I stayed out past curfew a few times without my parents ever finding out!

Why It Works: Here the candidate redefines the question from a negative (“the worst thing”) into a positive (“the biggest thing”). This ultimately works, though, because of the “add-on” reference to early family curfew avoidance – while his emphasis is on the positive action, he doesn’t duck the question entirely. Instead, he offers a “light” allusion to a common situation.

The worst thing I’ve gotten away with in college was sometimes cutting class the week before midterms and final exams. Especially in large, 400-student lecture classes where attendance wasn’t taken, I often found it was a better use of my time to study the class materials independently at home or with a study group in the library rather than sit in the classroom. I generally arranged things with a group of study partners so that one of us would attend the lecture, take good notes, and share them with the rest of the group. We rotated the note-taking responsibility between group members over the course of the term, which allowed us all extra time to cram for the exams.

Why It Works: This answer gives an excellent rationale for “breaking the rules” in the classroom, demonstrating that the candidate is resourceful, can organize and assign tasks within a team, and understands how to “think out of the box” in order to achieve a common goal.

There were times during college – especially towards the end of the year when money was tight – that my friends and I turned dumpster diving into an art form. None of us wanted to explain to our parents (again!) how we’d run short on food money (with me, it was generally because I loved to de-stress by going to out-of-town football games and concerts). So we’d do midnight raids on the upscale grocery store dumpsters and stock up on expired canned food and slightly-wilted veggies. We justified this to ourselves by deciding we were just doing our part to reduce landfill and save the environment. It probably wasn’t the smartest thing to do – but none of us got bitten by a rat or got tetanus or food poisoning.

Why It Works: This is a good example of picking a situation that, while potentially stupid, is a relatively common risk-taking behavior among college students – it wasn’t immoral or calculated to harm people. The candidate demonstrates maturity in owning that it might not have been the safest idea, while keeping her tone light as she jokes about how she and her friends justified their action.

Tips for Giving the Best Answer

Take Your Time: The thing to remember with the tricky questions is that it's fine to take a moment or two to frame a response. Then be honest, relatively speaking, so you are answering the question, but not in a way that would make the interviewer not want to hire you.

Emphasize the Positive: Keep your answer – and your tone – as positive as you can. Your interviewers are primarily interested in how you respond and in the composure and attitude you display while doing so.

Lighten Up: If you can, try to use humor to “excuse” behavior that might be construed as negative. If you go this route, though, make sure that your tone isn’t facetious or sarcastic. Tread lightly.

Use the STAR interview response method: In your answer, describe a past situation, the task (or challenge) involved, the action you took, and the result of this decision.

What Not to Say 

Don't share examples of seriously flawed behavior. Avoid all reference to situations that you know were morally or ethically wrong – such as cheating on an exam, breaking the law, or engaging in activities that were harmful to yourself or to others.

Nothing. While you don’t want to admit too much about a past indiscretion to an interviewer, neither should you try to avoid the question entirely by claiming perfection. Instead, choose an innocuous, common situation where you got away with something, owning your responsibility and sharing the lesson you learned from the situation.

Possible Follow-Up Questions

Key Takeaways

AVOID RED FLAGS: When asked about “the worst thing you’ve gotten away with,” choose an example of behavior that wasn’t serious. Don’t mention any action that might make an employer question your integrity as a professional.

SPIN THE QUESTION: Try to rephrase the question, turning it from the “worst” thing you’ve gotten away with into the “biggest” or “best” thing you’ve gotten away with.

REVIEW THE SAMPLE ANSWERS: And then create your own responses. Having thought about the question ahead of time will allow you to respond appropriately and with confidence should this question arise in an interview.