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Handle the Toughest Interview Questions like a Pro
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Perhaps one of the most nerve-wracking parts of applying for a new job—especially a dream job or a career switch—is not knowing what questions you’ll be asked during an interview. In general, questions will fall into four categories: personality, weakness, previous work, and reasons you’re leaving your old job. Within each of these broad categories, the interviewer will have tough questions they’ll use to get a deeper understanding of who you are, if you’re a good fit for the company, your thought process, and your capability of handling difficult tasks or situations.
If you can identify why a question is being asked, it will help you know how to form an answer that puts you in the best light. Try to answer with specific examples from previous experience and focus on how you grew as an employee and a person.
To help you prepare, here’s a guide to the toughest questions hiring managers are likely to ask and how to prepare rock-solid, truthful answers.
What is your greatest weakness? / What critical feedback do you receive most often?
The interviewer wants to see self-awareness in your answer and hear you’re working on self-improvement. Pick a criticism you’ve received and give a short explanation of how you’re strengthening this part of your personality or work process. Be honest, positive, and focused on pursuing a solution. Giving a vague answer can be a red flag that you won’t handle feedback well when you need to improve something.
Explain a time you overcame an obstacle.
This behavioral question seeks to understand how you handle obstacles and frustrations. A wise way to answer is to give a summary of the situation and your role, explain the action you took and why, and outline the results of your action.
How do you handle stress?
Stress is unavoidable in any career. Employers want to hear you’ll handle it with a good attitude and work to prevent it from affecting results, deadlines, quality of work, etc. Craft an answer that shows how you respond to common stressors in the position (i.e. deadlines, budget, communicating across multiple teams) with an example of how it has worked in the past.
What were your most positive and negative management experiences?
Understanding how you respond to various management styles will tell the hiring manager if you’ll be a good fit at the company. Answering tactfully but truthfully can be hard. Think of past managers and pick out how you were able to strengthen your soft skills under them. This shows versatility and the ability to adjust your own style to reach team goals.
Why are you leaving your current position?
Whatever your reason for leaving, make sure your response is honest but doesn’t include too much personal or negative detail. If you throw a previous employer under the bus, a new one will be hesitant to hire you. Turn the focus to what you want for your career future, how you want to grow with the new job opportunity, and what the company has to offer that you’re excited about. If it’s true, mention you’ll be leaving your old job on good terms.
Why should we hire you?
This question is an open door to show what differentiates you from other candidates. Have in mind experiences, skills, training, etc. that make you an ideal fit for the job.
Do you have any regrets?
This is another opportunity to show your self-assessment ability. If you can’t think of any regrets, frame your answer around how you’ve managed this. Or, pick a regret you can show you learned from and how you’re pursuing the career and life you want now.
Are you willing to fail?
Employers want to hear that you learn from failure and use the experience to improve in the future. They also want to hear you’re will to try new approaches and innovate while minimizing the risk of failure.
Describe a time when your job conflicted with your ethics. How did you handle the situation?
Here, the hiring manager wants to know you can handle tricky situations honorably, discreetly, and tactfully. When describing how you’ve done this in the past, remember to avoid oversharing and demeaning others—focus on your behavior and if you learned how to handle things differently next time.
Do you have any questions for me/about the company?
Hopefully you can think of good questions of your own after thoroughly researching the company. Think of questions that convey genuine interest in the position and the company’s future. Questions about company culture, growth plans for the next five years, and how they measure success are usually all winners.
Ultimately, the toughest interview questions can be handled with confidence and grace if you can frame your answers as showing personal growth, ability to adapt, and interest in helping the larger team or company succeed. Good luck!