During a job interview, hiring managers often ask tough questions to trip you up—not to make it hard but to get an accurate sense of your candidacy. Sometimes hiring managers are more interested in the way you respond than in your answer itself.
To increase your chances of landing the job you're applying for, it's essential to prepare for the interview. Thinking of solid answers to some of the toughest questions hiring managers commonly ask will set you up for success. Here's a look at the five challenging interview questions, along with suggestions on how to answer them and example answers:
1. What did you like or dislike about your previous job?
Hiring managers ask this question to assess your character. They would judge your character by listening to the attitude and tone with which you respond to the question. Your answer to this question can also help them determine whether you'll be a good fit culturally at the organization at hand.
To answer this question effectively, consider focusing on the positives of your previous role. You can talk about how your experiences there have prepared you to take on a challenging and progressive new role with a different employer.
Example answer:
I really enjoyed the people I worked with. It was a fun and friendly atmosphere, and I actually enjoyed going to work every morning. I think that the leadership team was also great. They all knew all their employees on a first-name basis and tried to establish personal connections. Also, I enjoyed the fact that the management strived to do more community outreach with local organizations.
2. What's your greatest weakness?
Hiring managers ask this question to get to know your weaknesses and strengths and ensure you're a good fit for the position.
To answer this interview question effectively, be honest, but make sure you choose a weakness that won't prevent you from succeeding in the role. For example, if you're applying for a project manager role, you don't want to admit that you're "not very good with time management." Further, provide an example of how you've worked to improve upon your weaknesses or learn new skills to address the issue.
Example answer:
Sometimes, I find it difficult to delegate tasks when I feel I can complete the task well myself. When I became a manager in my previous position, however, it became critical I learn to delegate tasks effectively. In order to maintain a sense of control when delegating tasks, I decided to implement a project management system to oversee a project's progress. This system allowed me to improve my ability to delegate tasks efficiently.
3. What makes you unique?
This interview question isn't an opportunity to confess odd quirks or weird habits. Instead, it's a chance to give the hiring manager insight into how you'd be the best candidate for the position while proving you're someone who can think on his or her feet.
To answer the question effectively, consider mentioning the skills listed in the job advertisement. Also, provide examples from your background. For instance, you can reference prior achievements or results from previous roles. You can also tell the hiring manager how your unique skills can help the organization succeed.
Example answer:
When solving problems, I apply both emotional aspects and logic in equal proportion. For example, I'm trained in search engine optimization and understand how to utilize analytics to ensure the success of a marketing campaign, but I also majored in graphic design and know how to apply creativity to projects as well.
4. How do you handle conflict with a coworker?
This behavioral interview question helps the hiring manager assess your people, communication skills, and self-awareness. It also helps them understand your strategy for handling workplace conflict positively and professionally.
When answering this question, avoid bad-mouthing the colleague you were in conflict with. Instead, focus on the heart of the issue and how you resolved it. Using the Situation, Task, Action, Result (STAR) method, you can provide a relevant and detailed real-life example. Here are the steps to answer the question successfully using the STAR method:
- Situation: Briefly describe the issue or conflict that occurred.
- Task: Mention what your role was in the situation.
- Action: Explain how you approached the issue and any steps you took.
- Result: Share results that prove how the outcome was positive.
Example answer:
Our marketing team had to create and implement a new digital marketing campaign, and I was responsible for overseeing the project and delegating tasks to each member of the team. One member was unhappy that I was chosen to lead the campaign over him and refused to complete his tasks. I asked him to meet privately to know why he was so upset. I listened to his side and told him I understood where he was coming from. I explained that if he works hard with our team to deliver a strong project, our manager may notice this and consider him for other responsibilities or promotions in the future. He agreed and completed his tasks, which led to a 40% client conversion rate and high praise from our manager.
5. Where do you see yourself in five years?
Hiring managers ask this question to understand your long-term career objectives and how you're striving towards your goals. They also want to know how this particular job will contribute to your success.
When crafting your answer to this interview question, get clear about your career goals. You can then relate these goals to the role you're applying for in the interview. Also, consider asking yourself if the organization can prepare you for your career goals. If you think the company you're applying with can't prepare you for your career goals over the next five years, you may want to reconsider the role or let the hiring manager upfront that you may not be with that organization for at least five years.
Example answer:
In five years, my ultimate goal is to successfully earn two certificates that are related to my role. I also took the time to review the company's website before this interview, and I found out that you provide your staff with education advancement opportunities that include pursuing certifications to advance their careers. Using the resources that the company provides its staff, I strongly believe that I can achieve my career goals and eventually advance to a management role within the company over the next few years.
Job interviews can be nerve-wracking, but you can increase your chances of success if you take the time to plan ahead. When you research and form your answers to the questions mentioned above in advance, you can approach the interview confidently.
Things You Need While Searching for a Job
Once you are armed with the knowledge about what kind of job will make you happy, there are core things to get lined up for a job search. Let's look at a few.
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What to Look for in a Job
Fun fact, most people will have about 12 different jobs in their working lifetime. This goes to show that finding a job that you love enough to hang onto takes some forethought and possibly a bit of trial and error. Just the same, you can make some plans in advance, helping you land in a position that leaves you perfectly content. Check out a few things to look for when looking for that perfect job.

Ben has worked with hundreds of job-seekers since 2016 to improve their resumes, cover letters, and job search strategies.
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