How to Answer Some Tricky Interview Questions

Worried about tricky interview questions? Don't be. Follow these tips and nail the interview.

Worried about tricky interview questions? Don't be. Follow these tips and nail the interview. 

Picture this. You’re all dressed up for your big interview, you sit in the waiting area feeling extra confident after a pep talk from your best friend, the interviewer calls you in, everyone gets settled and introduces themselves, and then they ask the first question and you’re completely stumped.

It’s no secret that employers ask difficult questions in interviews. But what do you do if you find yourself fumbling for words to answer these tricky interview questions?

Follow These Tips To Answer Tricky Interview Questions

Here are a few tips and tricks to get you through the awkward and tough questions:


If an interviewer asks tricky interview questions, you don’t have to answer right away! Sometimes it’s hard to allow space for silence in an interview setting due to all the nerves and excitement, but silence might be exactly what your brain needs to think of an answer to a tough interview question. So take a moment to pause and think.

You can simply say, “That’s a great question. Is it okay if I take a moment to think?” Or ask them to repeat the question to buy some thinking time. Either way, don’t feel pressured to blurt out an answer on the spot because it might not go well.

Prepare Notes

Bring a neat padfolio to your interview with an appropriate amount of notes (no more than the front of one page so you aren’t flipping sheets of paper around) to jog your memory. When you’re asked a tricky question, a few short notes about your strengths and experiences might help you connect the dots and form an answer. It’ll also show the interviewer that you’re prepared and serious about the position!

Consider What the Employer is REALLY Asking

Interviewers don’t just ask tricky interview questions for fun. There’s usually a reason. Or a question behind the question. Being able to decipher that is a crucial step in delivering an effective response. Oftentimes, tricky questions are asked so the employer can simply observe your thought process and the way you work through stressful and difficult situations. So there isn’t necessarily a right and wrong answer; they want to see how you think!

For example, a common tricky interview question is, “Tell me about a time you made a mistake.” While the interviewer does want to know what your mistake was, they most likely care more about how you can shine a positive light on that, how you overcame it, or your thought process while you worked to improve. Try addressing those things in your response!

Provide Examples

Difficult interview questions can make people ramble and say things that don’t have a coherent structure or thought process. As you’re thinking of answers to tough questions, remind yourself to include examples. This can help provide structure and clarity to your responses while giving the interviewer impactful content about your abilities and experiences.

Be Honest, But Positive

Several tricky interview questions are hard because they’re asking you to talk about negative topics. Past mistakes, weaknesses, bad parts about previous jobs, disagreements with supervisors, etc. The key with these questions is to be honest, but positive. Everyone has made mistakes and has weaknesses and bad experiences so don’t lie and say you haven’t just to avoid the topic or appear perfect. Instead, honestly address the negative aspects of the question in a very professional manner. But then put a positive spin on it!

On the other hand, some tricky questions like, “Where do you see yourself in 5 years,” might bring up information that you don’t necessarily want your interviewer to know. Maybe you just need a job to get you through the next few years until you find something better. That’s perfectly valid, but not something that you want to say in an interview. Make sure the details of your responses don’t hurt your chances of getting the job while still being honest.


One of the best ways to avoid being stumped in an interview is to practice. And then practice some more. It’s hard to come up with impactful answers to tricky questions in the heat of the moment during an interview. But if you’ve practiced ahead of time, answers should come to mind much easier. And while you might not be able to anticipate and practice everything the interviewer will ask, you can most likely adapt answers you’ve practiced to fit their questions.

To practice, write down and talk through your responses to as many tricky questions as possible. While you’re doing this, make sure your answers are coherent, positive, and honest while focusing on the real reason for the questions and content that’s appropriate to share in an interview setting.

Here are a few examples of tricky interview questions to practice:

  • What are your biggest weaknesses?
  • Where do you see yourself in 5 years?
  • Is this position similar to other positions you’re considering?
  • Why do you want to leave your current job?
  • Tell me about a time you made a mistake.
  • What did you like least about your previous job?
  • How do you handle stressful situations?
  • Why should we hire you?
  • Tell me about a time that you disagreed with a supervisor.
  • Why is there a gap in your work history?


If you’ve taken some time to think and look over your notes and you still can’t come up with a response to the tricky interview questions, offer up information that seems related and relevant instead of telling them you don’t have an answer. Simply say something like, “That’s a great question. I can’t recall a time when that happened but I can tell you…”

So while they might ask some tricky questions, remember that interviewers are not trying to trick you. They just want to see your thought process and gather all the information they need to make a decision. Practice ahead of time. Take a deep breath. You’ll get through it!

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