How to Answer 10 of the Toughest Interview Questions

Some of the toughest interview questions don’t seem so hard when you first hear them, like “Why do you want this job?” Others, like “What’s your biggest weakness?” give job seekers the jitters right off the bat.

So let me help. In honor of the 10th anniversary of The Great Job Sooner Blog–10 years helping people like you get a great job sooner!–I’d like to share 10 useful posts on answering tough questions like these.

First, here are some tips for getting a “10” on any interview question:

• Think about why the interviewer is asking the question. What are they trying to find out? As I explain in my post about the “weakness” question, interviewers don’t ask this question to trap you into disqualifying yourself. If you have the wrong idea why a question is being asked, you’re more likely to give the wrong answer (in this case, a defensive one).
• Make your answers both authentic and strategic. If you’re not thinking strategically, you’re likely to say the wrong thing. Without authenticity, you might say the right thing but the interviewer won’t believe it because they won’t trust you.
• Make sure you understand the question before answering. Take a couple of seconds to repeat the question to yourself. If it isn’t clear, ask for clarification.
• Be specific and concrete. And do use examples, stories and metrics whenever possible.
• Keep it positive. Don’t make former employers or co-workers look bad. Don’t offer negative information about yourself, either, unless the question specifically requires it.
• Handle negatives skillfully. The “sandwich technique” is a good place to start.

Now, let’s look at the questions.

10 of the Toughest Interview Questions and Answers to Ace Them

Click for tips!

1. What are your salary expectations?
2. Will you tell me a little about yourself?
3. Why did you leave your past job?
4. Have you ever been fired?
5. What’s your biggest weakness?
6. What’s a major mistake you’ve made?
7. What are your greatest strengths? (Harder than it sounds.)
8. Where do you see yourself in five years?
9. What is your work style? (Or: What is your management style?)
10. Why do you want this job?

Thanks for reading The Great Job Sooner Blog. It can help you succeed with even the toughest interview questions and get the job you want.  (This post was originally published in 2022 and has been updated.)