Interviewing for a new job is hard. It can be especially difficult if you have been out of work or unhappy in your current role for an extended period. No one likes rejection. When you are desperate to get a job offer, you are less likely to do or say anything that lowers your chances. You practice and refine the answers and stories you will tell to sell yourself to the hiring manager. At the same time, you are selective of the questions you will ask. However, you need to demonstrate courage by asking difficult questions during the job interview. Asking thoughtful questions will set you apart from other candidates, but asking difficult questions helps identify if you would be happy working for the company.
The key to winning the job interview is as much about the answers you give as it is about the questions you ask. Throughout my career, I have interviewed countless entry-level candidates up through Vice Presidents. What I found was no matter the level of role I was hiring for, most candidates failed miserably at asking questions. Even worse, they didn’t ask difficult questions. The biggest reason for not asking hard questions is the fear of looking clueless, showing a lack of confidence, or trying too hard to demonstrate a fit for the role.
Courageous Questions to Ask the Hiring Manager at Your Next Job Interview
Good hiring managers and good companies, for that matter, want candidates to demonstrate curiosity. They want to see you have the courage to ask hard questions. As a hiring manager, I want you to evaluate my organization and ensure we are fit for you. If you aren’t asking questions, especially difficult ones, I don’t see how you could be.
1. Share with me some examples of people who previously held this role that weren’t a fit and why?
Asking this question during the job interview shows that you are interested in understanding the potential weaknesses that could cause you to fail. Additionally, this question will provide examples of the critical soft skills required for the role that was likely absent in the job posting.
2. Based on this role’s current responsibilities, how many hours per week are needed to meet those requirements?
This question is a hard one to bring up during the job interview. You don’t want to give the impression you are unwilling to work extra hours. However, it is essential to validate that the requirements of the role will fit within your lifestyle. Any good hiring manager would share that sentiment.
3. What are some of the challenges or roadblocks I might face in this role?
This question says you already see yourself in the role. It demonstrates you are thinking about the problems you would be faced with should you accept the position. Asking this question during the job interview shows you understand that all roles come with challenges and that you aren’t afraid to deal with them.
4. What are the company’s core values, and how would you score the company on living up to those values?
Asking the hiring manager this question during a job interview is a respectful way of asking the shortcomings of the organization. It demonstrates you are proactively trying to understand how the employees interact with one another. Asking this question will also help you understand how serious they take the company culture.
5. What is the biggest challenge the team has faced this year?
Unfortunately, many hiring managers paint a rosy picture of the business, employees, and the role. Asking this question during your job interview shows awareness that no job or company is perfect. Uncovering the realities the team is facing helps you make an informed decision before joining a potential mess.
6. What behaviors do the most successful members of the team exhibit?
Asking the hiring manager this question during the job interview demonstrates curiosity for practical examples of success. Additionally, this question isn’t hypothetical; you are asking them to describe their top performers.
7. What behaviors do the people who struggle most on the team exhibit?
This question is an exceptional one to follow number 6. Asking the hiring manager this question during the job interview shows you are equally interested in what not to do. Be aware the hiring manager might find this question difficult, which is the point because it shows you are willing to ask tough questions.
8. Do you have any hesitations about my qualifications of fit for this role?
As a hiring manager, this question makes me uncomfortable, especially if the job candidate isn’t a fit. However, ask it you must because it shows you are confident enough to bring up and discuss your weaknesses openly.
9. Where do you see yourself in five years?
Such a great question to ask a hiring manager during a job interview! This question is difficult to answer and yet so important. It will help you understand the career path to ensure it aligns with your goals. Furthermore, it will help identify if the company has a good process for career pathing and how committed the hiring manager is to the organization.
10. Will you share with me how the company supports its employees with professional development opportunities?
What is great about this question is that it isn’t asking about promotion opportunities directly but will help you understand the potential of growing your career. Asking the hiring manager this question during a job interview gives you an idea of how serious the company is about training and upskilling their staff.
11. I read X on Glassdoor. Can you tell me more about this?
Show you did research and are informed and engaged in your job hunting process with this question. How the hiring manager responds to this question will help you identify if the organization values transparency. Additionally, if they place blame on the reviewer, it could be a danger sign. However, if they talk about what they have done to improve, it demonstrates they take employee feedback seriously.
12. What major challenges do you see me facing if I were to integrate myself into the company?
Asking the hiring manager this question during a job interview shows vulnerability and self-awareness. Furthermore, this question reveals the confidence to confront your shortcomings. It is especially important to ask this question when your experience for the role isn’t a perfect match.
