HH Happenings

Ideas, events and insights for employers and job seekers.

Five Engaging and Unexpected Questions to Ask Your Interviewer

If you’re actively applying and interviewing for jobs, you’re probably very focused on impressing employers and responding with “all the right things.” However, preparing your own questions is just as important for your interview performance and making a strong first impression. Additionally, the types of questions you ask during an interview will be integral to determining if the position is a fit for you. Consider these five engaging and unexpected questions to ask your interviewer:

How will you measure my success during my first 30, 60, and 90 days?

Upon starting a new job, it can often be unclear as to how you’ll be evaluated by an employer in terms of your performance and ability to fulfill the role from the start. Asking about the parameters by which your success will be measured will serve a few purposes. First, it will show the employer that you take yourself and the job seriously. Second, it will give you a baseline for what matters most within the new position. For example, if the ability to work well within a team will be heavily connected to your performance, you’ll know the importance of collaborating with colleagues to complete projects and reach goals.

What type of workplace culture is fostered?

Knowing what to expect from a company’s workplace culture can be a major factor in deciding whether the employer is a fit for your skills and personality. By asking the interviewer about culture, you’ll get a sense of the environment you’ll be part of each day – as well as insight into various cultural aspects, such as weekly team meetings, communication practices, and flexible work arrangements. Chances are your interviewer will appreciate your interest in the workplace atmosphere, as it will show initiative on your part to learn about the company at large, rather than just specifics about the job for which you’re interviewing.

What are the biggest challenges of this job?

Asking upfront about challenges that come along with the job can give you tremendously valuable insight about what to expect from the position’s responsibilities and requirements. This will give you some preliminary knowledge as to what difficulties you may encounter without being caught off guard. An interviewer’s response to this question may even lead you to discover that a job may not be a fit. Remember, this is not a bad thing! Bracing yourself with all the essential information will give you the launchpad to make the best decision for your career so you don’t end up in a position that you resent over time.

Will any on-the-job training be provided?

While most employers won’t expect you to know everything right off the bat, not all companies provide on-the-job training and development. Asking about on-the-job training is imperative for understanding what type of instruction and mentorship will be available both at the start of the position and throughout employment. From virtual trainings to continuing education, companies typically offer a multitude of training and development initiatives, many of which are required by new employees to undergo. Many candidates find comfort working for employers that provide the critical learning and resources to help them navigate their jobs and overcome roadblocks along the way.

What is the path to advancement?

If you’re like many driven candidates, you’re probably seeking a job that offers the potential for professional growth and increased earning potential. Inquiring about a company’s path to advancement will help you understand what opportunities within the organization will help you achieve your long-term goals. For example, if you’re hoping to obtain a managerial position over the next five years, ask the interviewer about the recommended pathway to earn this promotion. Some companies may have varying requirements and programs designed specifically to promote employee advancement. Whether it’s onsite training or one-on-one mentoring, knowing what’s available can propel your career growth and give you a launchpad for a more prosperous future.


Remember, a job interview is a two-way street, offering you the prime opportunity to learn about a position in greater detail, as well as gain clarity about the organization at large. As a candidate, recognizing the importance of asking questions will strengthen your demonstrated interest in the eyes of interviewers and increase your understanding of the employment opportunity, improving your interview experience overall. Preparing these questions ahead of time will also put you in the driver’s seat during the interview, boosting your confidence and motivation to excel.


Are you sick of constantly applying to the same types of jobs? Are you open to exploring different employment options? You may be surprised to learn about many in-demand and high-paying opportunities in various industries across the U.S. Launch your job search with HH Staffing, a Florida-based staffing firm, and browse our openings today!



Until Next Time,


Your Staffing Partner, Darrin Rohr- President, CEO, and Chief Servant

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Current owner of HH Staffing and Former Chief HR Officer for several successful Multinational Fortune 500 Companies. Brings a fresh perspective from decades of experience creating Great Workplace Cultures by building high-performance teams while leading and managing people from all different backgrounds. HH Staffing is headquartered in Sarasota, Florida, and is uniquely positioned to serve both local and national clients.