One Question You Always Ask In an Interview and Why

    Interviews are tricky to navigate for jobseekers, but we tend not to consider the other side of the coin. There’s a lot of pressure on the interview, too – they need to ask the right questions and make sure the candidate is up for the job.

    We asked some current business leaders how they navigate the interview process as they’ve built up their companies and expanded the roster. Here are the questions they always ask, and why.


    When an interview kicks off, why not open the floor and ease into the tougher questions later? This takes the pressure off both parties and sets the stage for a good conversation.

    “By simply asking in an interview, ‘tell me about yourself,’ you can learn so much about your potential hire,” said Steve O’Dell, Co-Founder and CEO of Tenzo Tea. “By asking this question, it allows you to see how they view themselves. Do they tell you about work experience first? Education? Hobbies? There are so many different ways to answer this question that it always is a great thing to ask so that you get to see what type of person you are interviewing.” 

    You can tell a lot about someone fairly quickly by seeing how they respond to this simple question.

    Honest Self-Assessment

    Talking about your strengths is one thing – we all know what we’re good at and the skills we bring to the table. Discussing weaknesses is trickier, demanding more maturity and self reflection.

    “Asking someone what their biggest weakness is a testament to how they view their abilities,” said Andrew Pires, Owner of The Maskie. “If you ask someone this question you will see how they view themselves quite quickly. This determines how confident your candidate is with your abilities and if they are quick to make adjustments. This question is one of the most difficult to answer, but if answered correctly it can get some great insight for your recruiting process.” 

    If the candidate is too arrogant – or too self-deprecating – that could be a no-go.

    Run Scenarios

    Interviewers know the ins and outs of daily operations within their company, so it’s not a bad idea to bring up some common scenarios that will likely occur on the job.

    “Asking potential hires about specific scenarios is a great way to know if they are qualified for the position,” said Kamron Kunce, Senior Marketing Manager for 4Patriots. “If they can walk you through how they would handle difficult situations then it will be clear that they are extremely qualified for the job. If answering questions about situations trips them up, then you should look for their qualifications and how fast they can adapt to certain environments.”

    These questions demand confidence and creative thinking – two essential traits.

    Past Experience

    Even if a candidate has only just finished their education or hasn’t spent much time in the workforce, they should be able to convey how their past experience will benefit you and your company.

    “Asking your potential hire about how their previous experiences will help them on the team is a great way to see their critical thinking skills and getting to know more about their resume,” said Chris Gadek, Head of Growth at AdQuick. “A good client will be able to break down how their past work experience will make life for them better at their new position. If they are able to do this with ease then expect their skills to transfer over easily, however, if they are not sure how it translates over then it should be seen as a red flag.”

    Just having a lengthy resume isn’t enough. The experience has to be relevant and applicable.

    Authentic Communication

    Everyone has endured those stilted, awkward interviews where nobody is showing their true personality. It’s up to the interviewer to let their guard down and be authentic.

    “Authenticity and strategy could be called the ‘yin and yang’ of good interviewing – except that they aren’t opposites,” said Author and Interview Expert Thea Kelly. “The opposite of authenticity is phoniness, and the opposite of strategy is randomness, or carelessness.”

    Sharing a funny story or a personal quip can be a good way to make everyone more comfortable.

    Real Qualifications

    Being qualified for a job means checking boxes, having the right experience, and being prepared to take on new challenges. You want to hear these things from the candidates themselves and not have to dig too deep to get answers.

    “A great question you can ask someone during an interview is, ‘what makes you qualified?’” said Melissa South, SVP of SwingTie. “It is simple and to the point, but does not lead them to an answer. Let them solve the puzzle in their head and give you an answer that can show you why they think they are truly good for the position they are applying for.” 

    You’ll be able to tell when someone is being real versus when they’re stretching the truth.

    The Reason Why

    Many employees will just apply to jobs simply because they can. It’s your duty to determine if they are really interested in the company or just wasting your time.

    “I think the most valuable information comes from asking a potential employee ‘Why,’” said Katie Lyon, Co-Founder of Allegiance Flag Supply. “Why this field of work? Why our company, and why are they qualified. Intentions breed motivation, which in turn creates productivity. If they are only looking for a paycheck, it will likely be a transient role. If there is a passion they feel towards the company mission, the greater the output will be.” 

    If they can relay personal stories or experiences with your brand, that’s a good sign.

    Apart from the Pack

    Smart candidates will know what they’re up against and be able to state why they’re better than the other applicants. Creating a healthy sense of competition yields interesting results.

    “The most important question I ask a prospect is, ‘What separates you from other candidates looking to work in law, and especially in our field of expertise?’” John Berry, CEO of Berry Law. “From their response, I can subsequently gauge what they value and assess how they view themselves. Moreover, it provides insight into their attributes, allowing them to give us qualities they believe will contribute to our firm’s overall success.”

    Look for applicants who speak highly of themselves and others, rather than jealous types.

    Inner Motivators

    Learning more about someone’s ambition can help you decide if they’re a good fit for your company. If you share similar goals and values, it could be a good fit.

    “I want to know what drives them daily,” said Dan Potter, Co-Founder of CRAFTD London. “Where does their motivation stem from? In essence, if it’s only for a paycheck, then the culture we represent may not be a fit. We symbolize a lifestyle, a message, and a vibe more than anything else. We are looking for others that buy into our aesthetic and can appreciate our mission. Being a self-starter and remaining inspired is crucial to maintain a productive workflow continuously.” 

    Some people just aren’t driven to succeed on a higher level, and that’s okay, but you need to look for those signs when conducting interviews.

    Showing Appreciation

    Your company was founded on a specific mission that means a lot to you and your peers. If you bring someone new on board the ship, they better have that same level of passion.

    “In our world, having a strong affinity for pets is paramount,” said Brandon Werber, Founder and CEO of Airvet. “One question that is in every interview is ‘What role do animals play in your life?’ The fact of the matter is, no matter what position the future employee takes in our company, they should have an appreciation for the services offered, the kind of compassion we embody, and with that, a shared inherent sentiment towards pets and their wellness.”

    Be ready to ask follow-up questions to make sure the candidate is giving you the full story and you aren’t being duped.


    Interviewers must remember that every job position has a unique set of challenges and expectations that can’t be ignored. Keep this in mind when asking candidates about their strengths and weaknesses.

    “I like to ask my candidates to define their strengths,” said Chris Vaughn, CEO of Emjay. “It’s interesting to evaluate their self-awareness, but even more, it’s important to see if they embody the strengths they claim to have. This way, I see what they can bring to the table—and if they claim to have a strength that isn’t demonstrated on their resume, it’s a sign that they may just be saying what they think I want to hear.”

    If an applicant has the right skill set and mindset, you can overlook minor flaws and get them to work right away.

    Passion Projects

    You don’t need to have a staff full of valedictorians and overachievers, but you should expect that new hires come to the table with a certain amount of passion for life.

    “Interviews should always ask what their potential hires are passionate about outside of work,” said Bill Glaser, CEO of Outstanding Foods. “I don’t want applicants to respond with what they think I want to hear—it’s great to see potential hires that have a passion for plant-based foods, cooking, and nutrition, but all of my employees have passions in addition to the work that we do, and that diverse background of thought lends itself to my company’s ability to innovate and succeed. I want to hear what an applicant really loves and why they love it to see if their energy will fit with our company culture.” 

    The most clean-cut and predictable candidates are not always the best picks for your company culture, as we all know.

    Long Term Thinking

    Job-hopping is just the status quo these days, and many applicant resumes will show this to be true. It’s okay to ask about how long they intend to stay with your company and their long-term goals.

    “When conducting an interview, I like to ask what the potential employee’s main goal is in working for my company,” said Jared Zabaldo, Founder of USAMM. “Is this a stepping stone to another opportunity that they hope to pursue? Are they interested in internal growth options? This can help me to better understand where they may fit as part of my team.”

    Sometimes it’s okay to have a short-term employee or two to fill some gaps, but you don’t want to deal with the stress of constant turnover.

    Lighten Up

    If your company has a laid-back culture and an open environment, you want to reflect that vibe in the interview and not make things too serious. Hit the main points in the interview, but also leave some room to freestyle.

    “In an interview, I think that it’s also important to learn about the person sitting in front of you, and not only about their skills and business experience,” said Heidi Robinson, Chief Operating Officer of Because Market. “So, it can be fun and lighten the mood to ask about hobbies. Plus, this can also provide some insight into the way an individual chooses to spend their time, which can sometimes provide more relevant information than you might imagine!”

    Some folks aren’t looking for a casual work environment, so the discernment goes both ways.

    Avenues of Achievement

    You can only get so much information from an online job application. The interview is your opportunity to find out more about an applicant and discover what really drives them forward in life.

    “To gain as much insight into a potential new hire as possible, I always like to ask what they hope to achieve by working for LTHR Shaving,” said Timmy Yanchun, Co-Founder of LTHR Shaving. “This can let me know if there is a potential for growth, or if this might simply be an opportunity to work toward a different goal, perhaps even a different career. This allows me to see who may be willing to change roles and learn new things, versus who may only be interested in the current position.”

    You might find that a candidate is better suited for another position, or maybe you just want to bring them on board for their unique energy and insight.

    Skills Oriented

    These days, there is no such thing as a static position within a company. Roles evolve and expand, and the best candidates will be ready to take on challenges unseen.

    “When holding an interview, I like to learn about the important skills that this potential new team member might hope to bring to the table,” said Rachel Jones, Head of PR for Shop Hope. “Many times, I can envision a particular role evolving and changing to accommodate growth, and I’d like to know if the person being interviewed has other skills that may not pertain to the particular job description. In this way, I can glimpse further down the road, and where this employee could be in six months to a year.”

    Be ready to ask questions that go beyond the scope of the interview for that particular position, because you’ll never know what you might find.

    Flip the Script

    Most interviews follow a strict format, and applicants are prepared to follow the script. It’s not always a bad thing, however, if they turn the tables and start asking questions about you.

    “Do you have any questions for me?” said Jim Beard, COO of BoxGenie. “It might not seem like it is important, but in my opinion, it is one of the most valuable questions to ask in an interview. Asking that question gives you an insight into how willing and eager a candidate is to learn about your company. Also, pay attention to what questions they ask. It can give you an idea of potential research they have done beforehand as well.”

    As long as the candidate is professional and appropriate, you can field questions and give honest answers in turn.


    Some classic interview questions stay in the rotation because they’re so effective at unveiling a person’s disposition and abilities. Ask about a particular experience in the past to hear a story and see what they’re made of.

    “One of the best things to ask an interviewee is about a time they overcame a challenge,” said Brittany Dolin, Co-Founder of Pocketbook Agency. “This is a common interview question, so if the candidate already has an answer prepared, this shows that they are already on top of things and reliable. Also, depending on how they answer the question, you can get a sense of how hardworking, creative and resourceful they can be under pressure.” 

    Not everyone is a gifted storyteller, so give some leeway and look for silver linings.

    Team Players

    Always consider how the candidate across the table will mesh with your current staff. You want to make sure they have the right personality and maturity level to work with established teams.

    “I really enjoy the interview process, as it’s not unlike a conversation where you’re simply getting to know someone, as you’re hoping to uncover whether or not this individual will be a good fit for your company culture,” said Jordan Dwayne, CEO and Founder of 6 Ice. “That’s why important questions about being a team player or working in situations where collaborations are needed, can provide some much-needed insight. After all, there are few things as important as your team actually functioning as a team.”

    Some people might be great candidates on paper, but fall short as a cultural fit.

    Working Habits

    When screening candidates, it’s not only about what a candidate will be working on, but also how they work. Things are a bit different in the remote work world, and they should be prepared to go with the flow.

    “What are we actually looking for during the interview process?” said Josh Stomel, Founder of Turbo Finance. “Well, it’s a candidate that can not only fulfill a need, but will provide the team experience that we’re hoping to build. Therefore, I always ask about their working process. Do they enjoy working with other team members, even if it’s done on a remote basis? Are team meetings a problem? What about brainstorming with the team? If a potential candidate doesn’t seem to enjoy any of these integral aspects of being a team, then they may not be the right fit.”

    Ask follow-ups about work habits and past team experiences to get the full picture.

    Unique Contributions

    When a position pays well and has prestige, you’ll get a lot of competitive candidates in the funnel. You need to ask the right questions that pit them against one another in a reasonable and productive way.

    “I like asking ‘What’s something unique about your experience that you can bring to this position that other candidates can’t?’” said Guy Bar, CEO and Co-Founder of Hyfit. “I want to know what stands this person out from all the other people I’m interviewing. It’s a question that makes the candidate really evaluate their skills and figure out how they can be different from the other people vying for the position. I’m looking for someone who stands out from the rest.” 

    It’s your decision at the end of the day, so make them work for it.

    Ready to Work

    It’s very difficult to gauge an applicant’s work ethic from a resume alone. Sitting down one-on-one can give you a better idea, but it’s all about the questions you ask and the responses you receive.

    “One of my favorite questions to ask is ‘How would you describe your overall work ethic?” said Scott Rosenberg, CRO of MaryRuth’s Organics. “It’s so useful to see how potential candidates describe their work ethic because I find the answer always varies. It’s the one question where you can have several unique answers. My favorite follow-up to this question is ‘How did the pandemic impact your work ethic’ because I’m always interested to see how people adapted when there’s a change in the company, especially one that requires them to work alone in their house.” 

    The last thing you want is someone unprepared to put in the hours, so tread carefully.

    Time and Place

    Some questions are hypothetical and not directly applicable to the interview, but they can still be valuable for their own reasons. Ask some out-of-the-box questions and inspire some creative responses.

    “A great question to ask is ‘How would you describe your ideal work environment?’” said Aylon Steinhart, CEO and Founder of Eclipse Foods. “I ask this because I want to make sure the candidate is a good fit for our work environment. It’s also a tough question to ask them because it forces them to either choose to tell a white lie or be honest. It’s a question that involves an in-depth answer and I always find the responses to be rather interesting. I can tell when someone is just saying what they think we want to hear.” 

    Watch out for generic replies or signs of uncertainty, because these can be giveaways.

    Success Factors

    We all have our own definition of success, and this is a great premise for an interview question. The answer can reveal insights about a candidate’s long-term goals and life philosophy.

    “I like to ask, ‘How would you describe success and what does it mean to you?’” said Derin Oyekan, Co-Founder of Reel Paper. “How a candidate defines success is always interesting to me. I want to know what they see as being a success and if that’s something that can work with how our company defines success.” 

    You don’t need to hear a profound answer to be impressed – just something that connects with you.

    Challenges Conquered

    The best job candidates are the people who have overcome challenges in the past, and can openly discuss their struggles along the way. This shows empathy and a sense of self-awareness.

    “I always like asking ‘What was a project you had trouble with and how did you overcome it?’” said Alex Keyan, CEO and Founder of goPure Beauty. “It’s an effective question because there are so many challenges and employees face and how they handle it says a lot about them and their problem solving and work ethic. I want to make sure who I hire is someone who can overcome a challenge or someone who is willing to hold themselves accountable for something going wrong.” 

    You will be working side by side with this person soon enough, so make sure they’re ready to face the challenges that await.

    Cultural Fit

    We often talk about company culture, but when you zoom out, you realize that culture is nothing more than the people that comprise the staff of a team or an organization at large.

    “When hiring, I not only look at candidates that have the skills but I also take into account the qualities the candidate might have that will be a great cultural fit within our team, which is why I always ask during an interview, ‘Do you work best alone or on a team?’” said Louis Leidenfrost, CEO of Paint Your Numbers. “This question helps determine if they’re suited for the types of assignments they’ll likely receive. Someone who enjoys solitary work and long stretches of uninterrupted time may not thrive in a position that requires collaboration or multi-tasking.”

    The people you hire will dictate the future culture of your company, so keep this in mind.

    Gauging Ambition

    Ambition is a sensitive word, and it’s not always viewed in a positive light. Be able to recognize whether a candidate’s ambition is coming from a good place or not.

    “When looking at a potential candidate for a position I am looking to fill, I look for someone who has a professional drive and big career aspirations,” said Michael Scott Cohen, CEO of Harper and Scott. “This is valuable to me because I want someone who is engaged in their career and has clear goals, so a question I always ask is, ‘Where do you see yourself in five years?’ Finding a potential candidate who is interested in career advancement and sees opportunities to grow within your company is essential because both are passionate about the company and motivated to work towards making it better. 

    You want every applicant to be driven and focused, but to also acknowledge team dynamics and respect the overarching mission of the company.

    Under Pressure

    Nearly every candidate will claim themselves to be a hard worker, but what does this really mean? Are they going to show up every day and put their full effort on the line, or back off when you need their help most?

    “One question I ask when hiring is if the prospect is capable of handling tight deadlines,” said Sean O’Brien, CMO of Modloft. “Working around tight deadlines in a fast-paced environment can become a little overwhelming for some employees, but there are also employees who enjoy the drive of working fast. This question is important because as the employer, you’re able to find out whether or not they will be capable of handling the workload and whether or not they can handle stressful situations.”

    There are no shortcuts in the world of business, and every applicant needs to recognize this truth first hand.

    Final Thoughts

    When you open up the floor for questions, does your applicant tighten up and shut down, or are they ready with rapid-fire questions that force you to think on your toes? Be ready, because some applicants will be better prepared than others.

    “Do you have any questions for me?” said Artie Baxter, CEO of Paperclip. “This question might sound like an easy question to ask because it’s common, but this question typically wraps up the interview. Prospects who are interested in the job will be prepared to ask relevant questions. This shows that they are interested and curious to know more.”

    It’s okay if you can’t answer every question perfectly, but don’t worry – you’re not the one being interviewed!


    Most of your applicants will be coming directly from competitors, so use part of the interview to gather some intel and find out more about these companies.

    “What could your current company do to be more successful?” said Eric Gist, CEO of Awesome OS. “This inquiry can give you a sense of whether interviewees see the big picture at their organizations. It may also show why they really want to leave their current jobs.”

    This is your chance to go not-so undercover and unearth some secrets.

    Sense of Certainty

    The most effective interview questions are often the simplest. Ask about why the person is sitting across from you in the first place, and what they want to do with their lives.

    “So many people out there have no idea what they want to do for a living, but they think that by going on job interviews they’ll magically figure it out,” said Author, Speaker, and Job-Hunting Expert Todd Bermont. “If you’re not sure, that message comes out loud and clear in the interview.”

    Some folks won’t have a great answer to the most basic questions, and that should tell you something right off the bat.

    Sharing Victories

    Asking about success stories is a great way to gauge someone’s passion and see if they’re ready for the next step. They should show excitement, enthusiasm, and a desire to conquer more.

    “In your most recent role, was there a time when you had to overcome a significant challenge?’” said Sunny Mills, Design and Production Director at YogaClub. “Use this question to get a sense of an interviewee’s critical thinking and analytical skills. You should also pay attention to how the candidate describes their behavior when faced with a challenge. Did they struggle or did they come up with an action plan and see it through?”

    We can all tell when the fire just isn’t there, or doesn’t come from real experience.

    Beyond the Office

    Work and money occupy so much mental real estate, we often forget about the world outside of the office. Ask candidates about their passions beyond work to get a full picture of the person you might hire.

    “One question we like to ask is: ‘What are you passionate about outside of work?” said Eric Kaye, CEO of Kayezen. “We look for people who share the culture and values of our company, namely, people with a passion for building their own physical and mental resilience, and who enjoy helping others do the same, and this question often provides insight into someone’s core personality and motivations.” 

    Talking Shop 

    Resumes are still relevant, but what about portfolios? These collections of real-life accomplishments can tell you much more than any bullet-point list on a page.

    “I think it’s useful to have a candidate walk you through their portfolio and explain the stories behind their projects,” said Michael Fischer, Founder of Elite HRT. “This gives them the chance to speak their mind about certain ideas and demonstrate further competence.”

    The more compelling and complete a portfolio is, the more you have to be excited about.

    Actual Enthusiasm

    Applying for a new job is a drag – we’ve all been there before. However, if your applicant is already showing signs of boredom in the interview, you might as well send them walking right then and there.

    “It’s important to know that the applicant is excited about your company and actually wants to be there,” said Tyler Faux, Co-Founder and CEO of Supergreat. “It sounds obvious, but it’s a real red flag if the person has no idea what they’re getting into.”

    They don’t need to be jumping for joy every two minutes, but you should expect some level of enthusiasm from your potential hires.

    Multitasking Abilities

    It’s the one thing nobody wants to talk about in the modern working world: time management. This is a crucial skill that makes a huge impact, no matter what position is in question.

    “If two people above you assign you a task, how do you choose which task to prioritize?’” said Lauren Bosworth, CEO of Love Wellness. “I like this question because it reveals the prospect’s example on how they would handle multiple tasks given at once. Asking this question will also give an insight into how strong their time management skills are.” 

    You might have the most talented applicants lined up, but unless they can manage their time effectively, it’s all for nothing. 

    The Full Scoop

    It’s not uncommon these days for people to jump between companies, seek new training, and totally change direction in their career altogether. Learn the full story about your candidates and get to a deeper level of understanding.

    “I’m always interested in hearing about their professional background within the industry and beyond,” said Denis Hegstad, Co-Founder of LiveRecover. “What other jobs have they done in the past, and what has it taught them about business and life? These are cool questions to explore and can lead to interesting conversations.”

    The interview process is high-stakes, high-pressure, and brings the best out of everyone. Ask the right questions so you can bring the best people on board your organization.



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