How To Answer Those Tough Situational Questions In A Job Interview

produced by Erin Yamagata; modeled by Hoku Gepp; modeled by Micaela Verrelien; photographed by Nicolas Bloise.
Picture this: You're in a strange office, sitting directly across from a hiring manager you just met. Things are going great — the conversation is easy, and you've prepared enough that you're able to confidently recount all of the reasons why you're perfectly qualified for the role. But then she suddenly asks you a situational question that completely trips you up.
You might know the kind of question I'm referring to: The type that asks you to tell the story of a time you messed up — without sounding incompetent.
Situational interview questions are designed to be a challenge, demonstrating that a candidate knows how to think on their feet and respond to curveballs, while also giving them a chance to display a slew of positive attributes, such as honesty, empathy, and humility. The only problem is, situational interview questions can be hard to prep for.
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For this reason, we chatted with a few experts — from hiring managers to recruiters to career coaches — who shed light on how best to face these types of challenging questions. Ultimately, acing a situational interview question is less about addressing a specific scenario and more about seeing the question underneath and demonstrating that you know how to handle yourself in a variety of circumstances.
Ahead, five career and hiring experts share their toughest situational interview question and how candidates should best answer.
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Q: Tell us about a time when you failed.

"It’s a touchy subject for a lot of us and difficult to admit; it can bring up a lot of insecurities, so it’s challenging to think about how to frame this in an honest, candid, and open way without giving a fake answer, but also not making yourself sound bad.
"This could be a proxy for other tough questions. Thinking about it ahead of time and confronting that in the privacy of your own head beforehand is key. Try to identify something that is an actual point of weakness for you, and then share what you’ve done since then to hedge against that happening again, and what you might do differently if you encounter it again.
"Inevitably, we’ll fail and fail again, so it's not just about lessons learned but demonstrating how you have and will modify behavior in the future."
— Cynthia Pong, Career Coach, Embrace Change

Q: Describe a situation where you had to work with a difficult manager or client and persuade that person to accept your point of view or convince them to change something they were doing.

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"To answer this type of question, the best approach is to follow the acronym STAR, which stands for Situation, Task, Action, Result. The best candidates will clearly and concisely explain the background of the situation, without including negative sentiment toward their managers or clients. This shows that they are mature and organized in their thought process.
"Candidates should then discuss the task or the problem that they were trying to change, followed by the action they took to improve the situation at hand. This further illustrates their thought process and gives the hiring manager insight into a candidate’s people skills and critical-thinking abilities. Sharing the result last will naturally close out the story, and top candidates can also explain their key takeaways here, as well as what they have learned and how they might act in the future."
— Michelle Armer, Chief People Officer, CareerBuilder

Q: Tell us about a situation when you realized a colleague or higher-up was doing something incorrectly or needed assistance that maybe didn’t seem obvious — how did you realize it and what did you do?

"We utilize situational questions in interviews [that are] tailored to the specific job role. We usually look for someone who is able to approach a conflict situation that’s uncomfortable for them and the other person with humility and an open mindset.
"[The question is about] being able to put themselves in the other person’s shoes and figure out how they would want a situation like this to go over. We do a lot of recruiting for entry-level, so people may not have the experience in an office setting. [It's about] being able to take a step back and think of different scenarios that may not be exactly the same, maybe with a classmate or a friend, and apply it.
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"[It's also about] being able to stop and think about the question instead of trying to think of what’s the best answer right away. It can be tempting to rush through it, but recruiters appreciate when someone puts thought into their answer and takes a second to really think through things. It's important to pull from a wide variety of experiences."
— Samara Green, Recruitment Operations Lead, Bench Accounting

Q: You're working on a project with a difficult coworker, and the project does not go as planned. How would you communicate with both your coworker and boss when debriefing the project, when it comes to discussing how you can be more successful in the future?

"When answering situational questions, it's important to think back to the skills needed to thrive in the role you're applying for. In this situation, you need to show how you communicate with people who aren't your workplace bestie when things aren't going your way. It's important to show that you can be diplomatic and communicate effectively during the good and bad.
"In other situations, you may need to show that you prioritize tasks effectively or that you can juggle multiple projects while pushing them forward, and keeping multiple teams involved informed on where the project is and what's stopping it from moving forward.
"This is where you fall back on your understanding of the role by highlighting the relevant skills needed to find success in your new position and the challenges you may face in this role."
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— Destiny Lalane, Recruiter at DrChrono

Q: When have you made a potentially career-ending mistake, and what did you learn from it?

"It seems like a simple question, but what I am looking for is if someone has been in charge of a project, or if they've been on a team, to even have the opportunity to make a big mistake.
"Beyond that, I want someone who can be comfortable with mistakes and learning. It shows humility and forward-thinking to be able to learn. I also want to find out if the person is willing to admit mistakes, as I want someone who can admit mistakes rather than hide them under the rug. It's quicker to correct an issue when we find it right away, rather than someone who wants to be perfect and hide mistakes until the situation becomes untenable.
"I don't ever want to trick interviewees or make an interview difficult for no good reason, as they are nerve-racking enough, but this question can reveal any 'career-ending' mistakes that are potentially unethical or problematic."
— Jessie Salsbury, MAHR, SHRM-CP
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