This Is How To Answer Your Most Dreaded Job Interview Questions

How do you explain getting fired? What do you say about that jerk boss you fled?

This Is How To Answer Your Most Dreaded Job Interview Questions
[Photo: Sladic/iStock]

There are a few questions you can’t wait for the hiring manager to ask you. A past project you worked on? You’ve got a great story to tell for that one. A time you failed? There’s an amazing redemption narrative tucked up your sleeve.


Then there are the questions you’re hoping to avoid–the ones that probe at the weak spots in your work history that you still haven’t decided on the best way to talk about. Here’s how to address four common scenarios that you’re dreading being asked.

When You Got Fired

“Why did you leave your last job?” That’s an easy question to answer when the reason is something like, “To take a better opportunity someplace else,” but when you’re job searching after being terminated or laid off, things can get a bit trickier.

The best solution here is honesty. As career coach Jena Viviano recently told Glassdoor, it’s often best to bring this up even before an interviewer has a chance to ask about it. “By bringing it up and being transparent,” she explains, “you are able to build trust [regarding] an otherwise uncomfortable topic.”

Whatever you do, don’t point fingers. People lose their jobs for any number of reasons, but rather than sharing the play-by-play or casting blame, the smartest approach is to keep it simple and talk about fit: You just weren’t the right match for that company at that time–but you are a great fit for this new opportunity.

When You Have A Resume Gap

“What were you doing between the dates of . . . ?” Much the same approach works when there’s a gap in the dates between two positions you held, or between your last job and your current job search: Just be as direct about it as you can.


Employers generally aren’t allowed to ask personal questions that don’t relate to your work history or help them assess how you’ll perform in the role, and you shouldn’t offer details that might open you up to bias. But when you took time off to raise a family, care for a loved one, go back to school, or backpack through South America, it’s best to distill that experience into two statements that make the following points (in this order):

  1. The main purpose/activity you focused on at the time
  2. What you learned from it

Don’t forget the second part! Writing for Fairygodboss, career columnist Jaclyn Westlake puts it this way: “The first sentence addresses the reason for taking time off, while the second line pivots the conversation to your applicable experience or enthusiasm for the role. The key is to answer the question succinctly, then move the conversation forward.”

When You’re Trying To Escape A Bad Boss

“How would you describe your relationship with your last manager?” If your previous boss was a total nightmare (or your current one is), it won’t get you very far to flat-out say so. Ridding yourself of a toxic manager is a totally legitimate reason to look for a job, but the key here is to avoid complaining and use the question as a chance to discuss one of two things, or perhaps even both:

  • How you handle challenges
  • Your preferred management style

Even if a hiring manager decides to phrase this question like, “What did you like least about your last boss?” you should still avoid taking the bait. Keep it scrupulously impersonal. For instance,

My last boss was a really talented operations manager with a sharp eye for detail. Working under her, I learned how to keep a lot of moving parts on track under pressure. But I find that I can do that best when I’m given a little more autonomy, so I’m ideally looking for a work culture that’s a little more hands-off.

When Your Last Job Was A Nightmare

“Why are you looking to leave your current position?” Here, too, a negative answer might be the most truthful one, but you’ll always want to put a more positive spin on it.


Your current job might be a total garbage fire, but complaining about it won’t get you far. Instead, make it less about them (your last employer) and more about you: “I feel I’ve grown about as far as I can in this role, and I’m looking for an opportunity to do and learn more.” This is among the easier “dreaded” interview questions to answer, since it lets you push the conversation back toward what excites you about the new role, and why you’re such a great fit for it.

In fact, that should be your goal when answering any challenging interview question: The faster you can get the focus back onto the amazing future you and the employer are going to have together, the better.

About the author

Rich Bellis was previously the Associate Editor of Fast Company's Leadership section.