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Chris Scherting

19 of the Best Questions to Ask in an Interview

Updated: Oct 13, 2022


19 of the best questions to ask in an interview - chris scherting

Hopefully you are reading this a few days before the big meeting and you are doing your homework, preparing to ace the interview. You are the motivated job candidate, going the extra mile and making your list of the best questions to ask in an interview. Or you are clueless and panicked because this is your first time getting an interview! Either way, you are in the right place.


It’s important to remember that the interview process is a two-way street. The hiring manager and company representatives want to find the ideal candidate to fill the open position. And you want to find your dream job, with a great boss, interesting work, and a company culture that fits your needs. You don’t have to settle for the first job offer you get.


I know it may sound crazy, but if you ask the right questions during an interview, you may find that the company or position is not a fit for you. It’s up to you to figure out the most important things that describe your ideal job and then create a list of questions to help identify the jobs you want to continue to pursue.


I’ve met so many people throughout the years who accepted a job they really didn’t want just because it was the first one that was offered. I’ve watched other people stay in a job in a toxic work environment because they were beaten down and scared to leave.


My goal is to help you find a job that is a great fit for you, where you can thrive and be happy. Asking the right questions can help you make a more informed decision. And note that my ideas below are just suggestions to get you thinking. I encourage you to make these your own, make them fit your personality. Many of them are interchangeable and could work in multiple situations.


Let’s walk through different interview scenarios and make a list of the best interview questions to ask.


Phone Screen Interview


During my career, I have used the phone screening interview as a tool to quickly assess a larger list of potential candidates and whittle the list down to the people I want to meet in person or on a video call.


My phone interviews are typically 15-20 minutes. I prepare a list of eight to ten questions that tie to key skills or traits I consider “must haves” for the job. These shorter conversations are a great way to cover a few resume highlights and ensure the candidate has some related experience or skills. I also judge the candidate on their verbal communication skills.


A few sample questions I ask candidates in a phone interview are:


  • Why did you apply to this job? What was most interesting to you? This question helps me to gauge your enthusiasm for this specific position and my company. I want you to want this job. Not just take any job.

  • What do you know about my company? I am looking for someone who did their homework and doesn’t BS their way through this question. This demonstrates your motivation and work ethic.

  • What kind of job are you looking for? I want to make sure my job is something they are looking for and they won’t be bored and leave quickly.


Even though these conversations tend to be shorter, I still hope that each candidate asks me questions as well. I want you to be able to figure out if my open position is a good fit for you too.


Here are a few questions you might ask that make sense for an introductory phone interview:


1. Why is this position open? Is it new or did someone leave or get promoted? If the position is new, that might be a good sign the company is growing but you will also have to figure things out from scratch. If you are looking for a company with a career path, this question will help you figure out if this is the right company. If someone left because of a toxic workplace or a bad manager, you might make the interviewer squirm a little when they answer this one.


2. What are the skills, experiences or personality traits you are looking for? This puts your potential employer in the hot seat. You are basically asking for the answers to the test. Hopefully their answer goes beyond the job posting and gives you real insight into the description of the best candidate.


3. How long have you been with the company? Hopefully the answer to this question will give you a peek into the company culture when they explain how long they’ve worked there, if they’ve been promoted, etc.


4. If I was your close family friend, would you recommend I work for your company? This is another great question that can uncover details about the culture. You make it personal for the interviewer. Listen for a hesitation in their voice or an increase in enthusiasm to help figure out if they are happy with the company.


5. What’s your favorite thing about working for [company name]? This is another good question to poke at company culture. If they struggle with the answer to this question, that is a red flag.


6. What are the next steps in the interview process? This is always a good question to ask at the end of the interview. When the prospective employer explains the timeline be sure to explain any conflicts you might have to set expectations about your availability. It’s ok if you have other work commitments or travel. They should be able to work around your schedule.


I would also advise you to not “phone it in” or treat this too casually. Don’t be lazy! Prepare for this interview just like you would an in-person meeting. Sit up straight. Smile. I can tell if you are laying on the couch half asleep! Take notes. It’s also ok to let the interviewer you are taking notes. It’s also ok to have your own questions written down.


First Interview with HR


Many companies begin the hiring process with Human Resources. This interview is also a screening interview but it will go into more detail about your background than what I described above in the phone screening.


Typically the HR recruiter will partner with the hiring manager to write the job description, post the listing online, set up the position in the applicant tracking system (ATS), and place paid ads for open positions. The HR representative will have a strong understanding of the background and skills needed so they can properly screen the job applicants.


You want to make a strong first impression, build a rapport, and move on to the next round of interviews.


Here are a few thoughtful questions for HR:


7. How long has this position been open? This will give you a feel for how frustrated or desperate the company may be to fill the role. The longer the position has been open, the more leverage you may have in negotiating an offer. On the flip side, the longer the role has been open, the bigger the mess you may be walking into with projects piling up. If the position has been open for a long time, you may want to ask a follow-up question about how the work is being handled.


8. What kind of training does the company offer to help shorten my learning curve on your processes, systems, and tools? Every company has a unique way of doing things. You will be more successful earlier in your tenure with the company if they offer training or have documented how to do things like submit invoices to be paid, how to complete expense reports, how to report tickets to the IT help desk, etc.


9. From your perspective in HR, what would I need to do in the first 30 days to be successful in this role? This question positions you as someone who wants to be productive and effective as quickly as possible.


10. Describe your company’s work environment. Beware of words like fast-paced environment or explosive growth. These words may be red flags hiding a work culture of long hours and unreasonable timelines. Creative and innovative may be too quirky or loosey-goosey for your personality. This question should help you figure out if the company’s culture is a fit for you.


First Interview with Hiring Manager


The first interview is typically one-on-one. The hiring manager should spend some time explaining the main responsibilities, projects, and tasks of the job. They should also try to sell you on the company, the department, and the job. In a world with a labor shortage, they should try to recruit you, to make you excited about the opportunity, to want to want to work there.


Some smart questions to ask of your potential new boss include:


11. What does a typical day look like? Some jobs are more consistent and repetitive each day, others vary greatly each day. Both can be appealing to different personalities. You need to figure out the kind of job that will be a good fit for you.


12. Describe your management style. Some bosses will be very rigid and want things done a certain way every time. Other managers may welcome new ideas and leave it up to you. Again, depending on your personality, you may feel more comfortable with a specific management style.


13. How will I be evaluated? Or what does success look like? I like this question because it shows the interviewer your desire to do a good job, to meet goals and be successful.


14. What would I have to do, so that in six months you would say “Wow, I am so glad I hired [your name], you really are a rock star!” This is one of my favorite questions to ask at the end of an interview. It shows a little personality and, like the question above, it shows that I want to kick butt!


Another category of questions for your prospective employer is based on your past work experiences. So, if this is your first job, you can skip to the next section.


Miscellaneous Questions Related to Your Experience


As you move from job to job you will observe many team dysfunctions and see how many companies have procedures or processes that hinder your success. These personal experiences will give you great insight into future jobs. As you gather career advice from others in your network, ask them about the types of situations you may want to avoid. Asking good questions around these situations can help you avoid bad work environments in the future.


You will have to use your own judgment on when these questions make sense to ask. My guess would be with your potential new boss or with a colleague who might be your peer.


15. Are sales and marketing aligned? In my role in marketing, if sales and marketing don’t get along or have an antagonistic relationship, it’s much harder for me to succeed.


16. Can you describe your strategic planning process? And what will my role be? I’ve worked in multiple companies who had zero strategic planning. They just went from project to project.


17. How well does your current team work together? This is a great question to ask to see if you can uncover any issues you might be walking into. Do the team members trust each other? Is it a “Yes Man” culture? How well do they handle conflict?


18. What are the biggest challenges you see with a family-run business? In my experience, I’ve observed family members with their own dysfunctions and pain points that kept the business from making difficult decisions to move forward. If the two siblings in key leadership roles don’t get along, your hands may be tied as well. This goes for corporate America and a family-run restaurant, and everything in between.


19. Does your company really value diversity? If so, how do they demonstrate that value? This is a great question to ask especially if you are LGBTQ+, a person of color, neurodiverse, etc. Companies can have their marketing department write about diversity on their website. It’s good to ask the interviewer’s perspective to see if the company really welcomes everyone and if it’s the right fit for you.


Remember what I said about the interview being a two-way conversation. You don’t want to end up working for a company with a culture that is not a fit for you. Or for a manager whose personality isn’t quite right for you. Asking questions during the interview process is the only way to figure these things out.


Again, I want to encourage you to pick and choose which of these common interview questions fit your personality and your years of experience. I highly suggest you choose a few for each phase of the interview process. Write them down and go in prepared. It’s ok to take notes during the interviews and to refer to your own prepared questions. It makes you look like you’ve done your homework, you are engaged and you are proactive.


Good luck! I think you may be starting your new job very soon!


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