17 Questions Hiring Managers Should Ask Candidates in 2023

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Going straight to the point, we have asked hiring managers and other specialists the question, "What's your one essential question to ask candidates in 2023?".  From "Where do you prefer to work?" passing by "How Would Your Skill Set Contribute to Company Success? to "What Did You Dislike The Most About Your Prior Position?" Here are the 17 answers to the question and the reasons why hiring people should consider these questions during a job interview.


  • Which Work Model Do You Prefer?
  • What’s the Biggest Challenge Ahead?
  • What Is Your Five-Year Plan?
  • What Motivates You to Do Your Best Work?
  • What Is Your Experience With Emerging Technologies?
  • Did Your Previous Role Impart Skills to Help With This One?
  • Can You Pitch This Company to Me as if I’m a Client?
  • What Would Be Your Perfect Training Course?
  • How Comfortable Are You With Employee Monitoring?
  • How Would Your Skill Set Contribute to Company Success?
  • Can You Describe a Job Situation Where You Had to Adapt?
  • Can You Keep Up With Change?
  • How Do You See Yourself Fitting Into Our Company Culture?
  • Why Did You Apply to Our Company?
  • How Do You Plan to Leverage Tech and AI?
  • How Do You Overcome Difficulties?
  • What Did You Dislike Most About Your Prior Position? 


Which Work Model Do You Prefer?

The debate on productivity, efficiency, collaboration, engagement, and other factors related to the work environment is still raging, but it is eventually up to the leaders and employees of each company to work out an arrangement. And asking your candidates this question in 2023 is not just essential; it is critical too.

Every person has a preferred work environment. This question will allow candidates to state this choice and give you an extra bit of essential information that will help you make the right choice when short-listing promising candidates. 

More importantly, the answer to this question will also tell you if the candidate will compromise with their preference or if they are rigid about their choice.

Riley Beam, Managing Attorney, Douglas R. Beam, P.A.


What’s the Biggest Challenge Ahead?

There’s no hiding that 2023 is looking like it could be a tough year. With interest rates and inflation going sky high, and a possible recession looming, a lot of companies are preparing for a rough 2023. 

As such, one question I plan to ask every candidate during hiring interviews over the next few months is, “what do you see as the biggest challenge ahead for this team, and our company as a whole?” 

The intent of the question is to see how in tune the candidate is with our vertical and the macroeconomic factors that affect it. I don’t expect people to give me a Ph.D.-like economics answer or a blueprint on how they would navigate the difficult times ahead—but I do just want to make sure they are not oblivious to the challenges that are inevitably coming. The question is more about their wherewithal than anything.

John Ross,  Chief Executive Officer, Test Prep Insight


What Is Your Five-Year Plan?

Ask your candidates where they see themselves in five years. The information gleaned from this question can reflect a lot about a person and what they expect from the job, how long they may stay at the company and if they are a good culture fit. 

Companies have to use many resources to hire people, so you want to ensure it is the right fit for both of you. You can learn a lot about someone by learning their goals and using the information to decide if they are a good fit for your company.

Ann McFerran, CEO, Glamnetic


What Motivates You to Do Your Best Work?

When a candidate understands their work motivation, it's much easier for you to see how they align with your company culture and if they will be a good fit at your organization. For example, if a candidate tells you they are motivated by collaboration, then you know they will be a better asset to your team than someone who prefers to work alone. Candidates should also be able to articulate why they want to work for your company specifically; generic answers usually mean they are not passionate. A great answer would be something like, "I am motivated to enhance customer experience, and learn about their needs and how they use your product." This type of answer shows passion and attention to detail, and that they have thought about why they want to work for you.

Anthony Martin, Founder and CEO, Choice Mutual


What Is Your Experience With Emerging Technologies?

In 2023, one essential question to ask candidates is, “What is your experience with emerging technologies?”

This question is important because, by 2023, newer technologies like artificial intelligence, machine learning, and automation will probably be widely adopted in the workplace, so companies will need employees familiar with these advancements.

Asking this question ensures that you hire candidates who are knowledgeable and comfortable with emerging technologies and who can start strongly in their new role.

Shaun Connell, Founder, Writing Tips Institute


Did Your Previous Role Impart Skills That Help With This One? 

With the pandemic being so disruptive, job seekers have been very reflective about what’s important to them. This question is vague enough to allow the candidate to reveal their state of mind post-pandemic, and what their priorities are. 

It can also give insight into what they’re most proud of in their professional life, all helpful information that can help you decide. I doubt any candidate’s answer will be the same as another, giving you an easy differentiator.

Monte Deere, CEO, Kizik


Can You Pitch This Company to Me as if I’m a Client?

I enjoy asking interviewees to pitch my company to me as if I'm a potential client.

The interviewee's response will answer a few questions of mine:

1. Did this potential employee do research about my company?
2. Can they articulate what we do as a business?
3. Do they know how to communicate and sell?
4. Do they know the difference between us and the competition?

Salespeople and marketers will obviously provide a better answer. Even so, it works for all departments as you'll understand what an employee values at your company.

Scott Lieberman, Owner, Touchdown Money


What Would Be Your Perfect Training Course?

We ask, “What would be your perfect training course?” to gauge: 

  1. the interests of the candidate in relation to their work role and 

  2. whether we can get external training for them in line with their genuine training aspirations and goals. 

This also shows them from our side that we're serious about nurturing their learning requirements and helping them to grow with our approach to training.

Dawn Wood, HR Manager, Woodyatt Curtains


How Comfortable Are You With Employee Monitoring?

With remote work becoming mainstream, employers are increasingly adopting employee monitoring tools to correctly evaluate the performance and productivity of distributed teams.

With 40% of employee internet access time spent outside work-related activities, employers are pivoting to these monitoring tools (from internet usage to screen capture) to ensure they are paying their employees for time spent on work.

However, not all employees are comfortable with monitoring tools. For some, monitoring tools are a digitized form of breathing down their necks and intruding on their privacy and flexibility—the latter being the major spice of remote work.

Therefore, ask candidates if they are open to employee monitoring when interviewing them.

Ask the candidates to what extent they are open to being monitored without suspecting their employer is encroaching into their personal space.

Lotus Felix, CEO


How Would Your Skill Set Contribute to Company Success?

In 2023, companies should look at one essential question when interviewing candidates: "How would your skill set contribute to our team's long-term success?" This shift away from narrow technical questions towards a broader focus on long-term value will help paint a comprehensive picture of how each candidate can positively affect the entire organization.

Asking open-ended questions designed to gauge a potential hire’s ability to deliver on ambitious goals while flawlessly executing daily operations will help ensure an effective candidate fit in 2023.

By taking a more visionary approach, employers can find hires with the right mindset and competency level for the job and introduce them into their adapted workflows as quickly as possible.

Ram Thakur, Founder, Solution Suggest


Can You Describe a Job Situation Where You Had to Adapt?

My go-to question in 2023 for evaluating candidates is: "Describe a job situation where you had to adapt to an unexpected situation." 

My marketing team went through a whirlwind of change during COVID, post-COVID, and switching to and learning the remote work environment. COVID taught us that external factors can have a profound effect on the way we do business and how we approach work.

If a candidate has significant experience in having to adapt to unexpected situations at work, they usually are enthusiastic and quick to dive into this question. While interviewing, this question helps me gauge their reaction to an open-ended question that puts them on the spot, and I get to see if they are adaptable as an employee based on their example. 

Being an adaptable employee in 2023 is ultra-important for successfully navigating the inevitable challenges we all face. Adaptability is one of the key attributes I look for in candidates, and that will continue in 2023.

William Varney, Product Strategist, Megaphone Marketing


Can You Keep Up With Change?

When I'm interviewing prospective candidates for employment in 2023, my essential question will be: “Can you keep up with changes?” 

Our rapidly growing digital world brings about a dizzying array of innovations and updates: technological advances, new industry trends, and novel approaches to problem-solving. 

It's impossible to anticipate every kind of change one might need to adapt to, but this question helps me assess how well one can handle the unexpected and out-of-the-box thinking that comes part and parcel when exploring the latest opportunities.

In other words, can candidates roll with disruptive changes, or will they be stuck in their ways? Can you keep up with the changes? I sincerely believe this is my one essential question for improving hiring outcomes in 2023.

Derek Bruce, Senior Director, Skills Training Group


How Do You See Yourself Fitting Into Our Company Culture?

One of the most important goals for any HR manager is to bring in talent that fits right into the organization's values, culture, and norms. Creating a productive work environment where everyone is free to pursue their full potential totally depends on the values and corporate culture in place.

It is, therefore, essential to know how prospective talents will fit in and whether they will contribute positively to reinforcing these corporate values or not. Besides, this is one question that doesn't get answered through cover letters or CVs. It also helps HR to establish how well the prospective talent is conversant with the company, its values, and the expectations it has on employees.

Also, this question gives future company talent a chance to explain how they intend to merge their own personal skills and values with those of the organization they want to work for.

Jennie Miller, Co-Founder, MIDSS


Why Did You Apply to Our Company?

When interviewing anyone, I want to know why they have applied to join our firm in particular. I’m looking for an answer that shows the candidate has done their research and has a definite purpose in choosing us. 

If they have made a considered choice and have a strong awareness of our firm’s specific values, principles, and ethos, then it will make the onboarding process much simpler if they are successful. 

It also facilitates integration and makes it easier to maintain the company culture and unique dynamics of our workplace. We put a lot of effort into our hiring process, and it’s important that candidates invest equally. Taking the time to learn about our individual firm shows this.

Martin Gasparian, Attorney/Owner, Maison Law


How Do You Plan to Leverage Tech and AI?

I believe one essential question to ask candidates should be: "How do you plan on leveraging technology and AI to improve your workplace performance?" This question is important because it will give the interviewer insight into how a candidate plans to stay ahead of the curve.

It will give you a better understanding of the candidate’s ability to think creatively and critically adapt to new technologies and help the interviewer determine if the candidate is capable of utilizing new and innovative tools to increase productivity.

Asking this question will ensure that the company is bringing on individuals who can handle the changes and challenges of the ever-evolving technological landscape.

Arkadiusz Terpilowski, Head of Growth & Co-founder, Primetric


How Do You Overcome Difficulties?

The past few years have been challenging, especially as we've moved from in-person work to a hybrid or remote environment. Ask candidates, "What has been the most difficult shift for you since the pandemic began and how have you overcome it?" 

This two-part question gives you insight into the personal challenges the candidate has faced, but also how they've problem solved and ultimately thrived in their new environment.

Harry DiFrancesco, CEO, Carda Health


What Did You Dislike Most About Your Prior Position?

The most important question we ask any potential employee is "What did you like the least about your prior positions?"  

Most interviewees don't have a prepared answer for that and give you honest answers that are a great insight to determine if your company and position would be the right fit for them.  

We view every hire as a two-way street where the match has to be good for the potential employee as well as us. We are not only trying to determine skill level and true interest but also if there are elements of our position and company culture that won't be a match.  

Hiring is only a win-win if both the new employee and the company are happy in the long term.

Dave Haney, CEO, Surety Systems, Inc.