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 this post I’ll offer quick tips with links to 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. Have an agenda, but also be transparent and true to yourself.
- 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
- What are your salary expectations?
- Will you tell me a little about yourself?
- Why did you leave your past job?
- Have you ever been fired?
- What’s your biggest weakness?
- What’s a major mistake you’ve made?
- What are your greatest strengths? (Harder than it sounds.)
- Where do you see yourself in five years?
- What is your work style? (Or: What is your management style?)
- Why do you want this job?
Your Tricky Questions Aren’t the Same as Everybody Else’s
The list above may be the toughest interview questions for job seekers in general, but of course your situation is unique. What questions, perhaps based on your industry or work history, will be most challenging for you? If you’d like one-on-one help with one or more worrisome interview questions, feel free to reach out.
(This post has been updated in 2026.)
