New! Fishbowl by Glassdoor. Dive into authentic, anonymous conversations with a community of professionals like you. Learn More.


10 Tricky Interview Questions & How to Answer #LikeABoss

Posted by Glassdoor Team

Career Advice Experts

Last Updated April 17, 2019

It’s the question that none of us want to be asked: “Why were you fired?

You’re on the edge of your seat, heart pounding, beginning to sweat. You have only a few seconds before you need to formulate a response. How can you give an answer that both honestly explains the situation and still makes you look good?

To find out how to answer tricky questions like this one, and more, we sat down with Kerry Hannon, seasoned career expert and author of Love Your Job: The New Rules for Career Happiness.

“We know job interviews are incredibly nerve-wracking. You have total strangers grilling you, and they’re scary, and it can be intimidating,” says Hannon. “But you’ve got to have some chutzpah,” she adds.


Take a reflective, rather than a reactionary tone, Hannon advises. “Pause before you respond. Even repeat back the questions. Buy yourself some time to gather your response. Don’t just jump off with an answer… And then come out with a confident and calm response.”

Here are a few of the toughest interview questions, and Hannon’s advice for blowing them out of the water.

1. Why were you fired?

Getting fired is way more common than we might think, and that can be a comfort. “The most important thing to focus on is that for your own sanity. Realize that almost everybody has been fired at some point from a job. The interviewer has probably been down this road themselves,” says Hannon. She adds that this question might trigger an emotional reaction in you, even if you prepare for it, so it’s important to be careful, honest and brief. “Position that situation as a positive learning experience,” advises Hannon. She recommends talking about how your expectations for the job were different than what the reality of the job was.

2. Tell me about a time when you had to work with a difficult person.

Once upon a time, Hannon says she had a very difficult boss, so it's easy for her to relate to this question. “It was really challenging working with this individual, but what it taught me was empathy, because it made me think about what were his challenges right now.” Maybe he himself was working for a difficult boss, or was having his own struggles with the job, Hannon says. Instead of making a knee-jerk reaction and complaining, this is a time for introspection.

“You might say in your interview, it really taught me to take the time to find out what my boss was going through... and understand why we had this communication issue,” she counsels.

3. Why did you choose your profession?

Questions like this one aim to prompt you to show your passion and drive for your career — a time to give a full background of why you love what you do. “This is the time where you can tell your story. Interviewers love this. It gives them a peek into who you are, what kind of person you are, what kind of communicator you are, what sort of drive and motivation you have,” she says.

4. Where do you see yourself in 5/10 years?

This is a tricky question because it can force you to reveal that you don’t plan on having a long-term career with the employer in question. Hannon advises against revealing this, and instead speaking more generally about the type of work environment you would like to see yourself in. “What I like to say is, 'I imagine I’m going to be working alongside really smart, positive, enthusiastic people, who will encourage me, and who I’m learning new things from, and that I’m being creative,” she says. Additionally, speaking about the specifics of what type of job title and specific responsibilities you want isn’t always the best approach. “Rather, make it a really collaborative answer about [what] kind of work environment you hope you’re in and why,” Hannon adds.

5. What’s wrong with your past/current employer?

Hannon advises against going into detail on these questions — especially if those details are negative. “Be generic as possible, and stay away from real specifics here,” she counsels. “Negative things are never somewhere you want to go in an interview.”

6. Tell me about the worst manager you ever had.

This question is not about throwing your old manager under the bus, but rather reflecting on what you learned from working with them. The phrase “my worst boss taught me…” is one Hannon mentions as being a good way to frame a difficult experience you had with a manager. “It’s all about taking the high road and being gracious in many ways,” she says.

7. What’s the worst job you ever had?

Again, the blame game is never a good interview strategy. Hannon recommends saying something like: “the job wasn’t quite right because there was a lack of opportunity that I thought might have been there, but didn’t see.” Neither is blaming the “bad job” on your former manager, coworkers and company, or yourself. “Refocus and reframe it, but try to move on as quickly as you can,” adds Hannon.

8. What attributes do you have that will support you in this role?

Hannon recommends answering this question in the context of why you have enthusiasm for your broader career. In talking about what about the job excites you, explain how you’ve specifically worked towards being good at it. “If there’s a profession you really love, you can just really fire up and say … that’s why I developed x, y, and z skills. That gives you the chance to zoom, to show your excitement, energy and passion,” she says.

9. Why did you leave your last job?

If you’ve left your last job and are looking for a new one, chances are it wasn’t quite satisfactory. But there’s no need to talk about the negatives of the job or the company. “It’s always reframing it into what you learned from that experience, not why it was a bad thing,” says Hannon. “Don’t blame them, and don’t blame yourself, just say it wasn’t a good fit,” she continues.

10. Do you have any questions for me?

“You need to be asking them tough questions,” says Hannon. It is through these questions that you can figure out whether or not the company is a good fit for you. In addition, the questions you ask can be a means to show that you have thoughtfully researched the company. Don't ask questions that you can find the answers to on their website, but questions that show a deeper level of thinking, like "What is your long-term vision for the company," "what are the biggest challenges your team is facing" or "what does it take to be successful here?"

blog 28

Browse Open Jobs

Find Jobs Near You

Blog HomeInterviews10 Tricky Interview Questions & How to Answer #LikeABoss