Looking for a few “would you rather” questions that can provide insight into the way an applicant thinks? Whether you’re looking for lighthearted questions that break the ice or more serious prompts about entrepreneurship or management these suggestions can help. Here’s a list of more than 200 smart interview questions you can use to collect information about a potential employee.

Funny Would You Rather Interview Questions

stressed worker

Yeah… Interviews can be stressful.

Here are some “would you rather” that would bring a smile to both the interviewer and applicant. These questions can serve as a pressure release valve at the beginning of an interview and an effective way to get everyone comfortable. These questions can also help a candidate get relaxes and open up a bit more.

  • Would you rather bike or walk to the office?
  • Would you rather eat a cookie or a cake?
  • Would you rather serve under a handsome manager or a beautiful supervisor?
  • Would you rather be seatmates with a handsome guy or a pretty lady?
  • Would you rather have coffee or tea during office breaks?
  • Would you rather talk to HR or the general manager?
  • Would you rather work in our office on the moon or here on Earth?
  • Would you rather fly on a company-sponsored plane or a commercial flight?
  • Would you rather be a singer or a dancer for the team?
  • Would you rather go for a team hike or a team swimming lesson?
  • Would you rather have just coffee or coffee and donuts during breaks?
  • Would you rather frown or smile as you enter the office?
  • Would you rather protect yourself from infection by wearing a mask or not?
  • Would you rather wear eyeglasses or contact lenses?
  • Would you rather have free coffee or free soda in the company’s vending machine?
  • Would you rather have a romantic relationship with a team member or not?
  • Would you rather hear jokes or ghost stories?
  • Would you rather eat out during lunch or enjoy the food in the company cafeteria?
  • Would you rather save or invest your salary?
  • Would you rather have a Friday night out with the team or just stay at home?
  • Would you rather have a weekend or a weekday day off?
  • Would you rather have a friendly supervisor or a strict one?
  • Would you rather be friends with the company’s owner or your supervisor?
  • Would you rather introduce yourself to the secretary or the sales assistant?
  • Would you rather work in sales or customer service?
  • Would you rather write or do calculations?
  • Would you rather have an analog alarm clock or a digital clock on your workstation?
  • Would you rather watch TV during breaks or play video games?
  • Would you rather be seated way behind the office or in front of the office?

Would You Rather Questions about Business

Know the applicant’s insights, beliefs, and principles about business with these probing questions.

  • Would you rather have your own business or work in a company?
  • Would you rather stay employed in a company or run your own business?
  • Would you rather run a small to medium-scale business or a large corporation?
  • Would you rather have a good profit or a good work-life balance?
  • Would you rather be a manager of a startup business or a long-established business?
  • Would you rather work in a dynamic company or a stable firm?
  • Would you rather have a product-related business or a service-related one?
  • Would you rather have a food business or a retail business?
  • Would you rather be a businessman or a manager?
  • Would you rather close your business when it’s not doing well or continue on?
  • Would you rather save or borrow money for business capital?
  • Would you rather do it yourself or hire people even though your business just started?
  • Would you rather have a pet store or an animal shelter?

Related Reading: 41+ Example Answers About Going Above and Beyond for Interviews 

  • Would you rather go for solo entrepreneurship or a corporation?
  • Would you rather invest in stocks or in mutual funds?
  • Would you rather be called an entrepreneur or a CEO?
  • Would you rather run a family business or one that does not involve family?
  • Would you rather save up the profit or invest it to expand the company?
  • Would you rather partner with a marketing executive or a customer service supervisor if you were to run a business?
  • Would you rather adopt a B2B or a B2C business model?
  • Would you rather have an online business or a brick-and-mortar business?
  • Would you rather have partnerships or a solo show?
  • Would you rather have work-from-home arrangements or in-office work schemes?
  • Would you rather own a business or be partners with an entrepreneur?
  • Would you rather focus on your business or stay as an employee?
  • Would you rather rent a space for your business or use a space on your own property?
  • Would you rather borrow money from a bank or from a lending firm?
  • Would you rather place more budget on R&D or on marketing?
  • Would you rather hire a general manager or a department manager in the first few months of your business operation?

Would You Rather Questions about the Workplace

Thinking about the big questions in life.

What kind of work does the applicant prefer? Ask him or her using these questions to gain insight into the type of environment a candidate would prefer to work in.

  • Would you rather work in your own office or on the common floor?
  • Would you rather work in an enclosed office or one with outside-facing windows?
  • Would you rather have an office with plants or none at all?
  • Would you rather work in an open-air office or an air-conditioned one?
  • Would you rather work in an office or at home?
  • Would you rather have a standard computer desk or a sit-and-stand desk?
  • Would you rather have your own desk or share a cubicle with someone else?
  • Would you rather have a carpeted or a tiled workplace?
  • Would you rather work on the ground floor or an upper floor?
  • Would you rather work in a quiet, peaceful workplace or one that is busy and fun?
  • Would you rather have a computer chair or a bean bag?
  • Would you rather the company have a nap room or none?
  • Would you rather work in a home office or a company office?
  • Would you rather have a library in your workplace or none?
  • Would you rather have a pantry in your office or none?
  • Would you rather work in a toxic workplace for job security or resign and risk finding a new one?
  • Would you rather work in a sitting or standing position?
  • Would you rather work in an office or out there in the field?
  • Would you rather sit in a normal office chair or on an ergonomic chair?
  • Would you rather invest in new workplace equipment or repair damaged ones?
  • Would you rather go for old but functional office furniture or brand-new ones?
  • Would you rather work in a classical workplace or a contemporary one?
  • Would you rather work online or offline?
  • Would you rather have your own private phone on your work desk or just a general phone line for the office?
  • Would you rather take off your shoes in your workplace or leave them on?
  • Would you rather have a snack bar in your office or none?
  • Would you rather allow cell phones in the workplace or prohibit them?
  • Would you rather allow pets in the workplace or prohibit them?
  • Would you rather leave your workplace on time or render a bit of overtime?

Would You Rather Questions for Entrepreneurs

These questions are perfect if you want to see if the applicant has an entrepreneurial streak. These can be good questions for prospective managers or innovation departments.

  • Would you rather be an entrepreneur or a high-ranking executive?
  • Would you rather partner with someone or run the business yourself?
  • Would you rather go with multiple partners or just a single partner?
  • Would you rather hire a team right away or not?
  • Would you rather build a competitive business or a complementary business?
  • Would you rather establish a service-oriented or a product-oriented business?
  • Would you rather build your own brand or market another brand?
  • Would you rather be a distributor or a source?
  • Would you rather be a business mentor or a critic?
  • Would you rather do the final interview for applicants or let your HR manager do it?
  • Would you rather have a personal assistant or not?

Related Reading: 97+ Critical Thinking Questions to Test Employee Decision Making 

  • Would you rather complete your business registration before your business opens or work it out along the way?
  • Would you rather have a team of professionals or newbies?
  • Would you rather employ regular workers or freelancers?
  • Would you rather have a company-sponsored car or a fuel allowance for your own car?
  • Would you rather save up or borrow money to generate capital for your business?
  • Would you rather focus on quantity or quality of output?
  • Would you rather start your business right away or think about starting it for a month or two?
  • Would you rather be a leader or a boss?
  • Would you rather establish a small company or a big one?
  • Would you rather make all the decisions or the board?
  • Would you rather sponsor an event or be sponsored?
  • Would you rather invent a business concept or follow a proven one?
  • Would you rather compete or complement?
  • Would you rather give more importance to company growth or employee growth?
  • Would you rather have employees straight out of college or ones with experience?
  • Would you rather hire experienced but traditional managers or inexperienced but innovative ones?
  • Would you rather give value to innovation or adherence to standard business practices?
  • Would you rather make the bulk of your team work in the field or in the office?

Would You Rather Questions for Managers

More often than not interviews are now conducted via Zoom.

Ask these questions for those who want to apply for a managerial position so you could get an idea of their managerial style.

  • Would you rather focus on marketing or customer service?
  • Would you rather listen to your subordinate’s explanation or a complaint from an angry customer?
  • Would you rather be addressed as “sir/ma’am” or just your name?
  • Would you rather have your team work 8 hours or 10 hours a day?
  • Would you rather have your team work overtime or leave the office on time?
  • Would you rather fire or guide a constantly erring employee?
  • Would you rather allow the team to make decisions or do you make the decisions?
  • Would you rather give the team a free hand in their work or guide them using your experience?
  • Would you rather hire an expert who demands a high salary or a new graduate who is fine with an introductory salary?
  • Would you rather have daily or weekly team meetings?
  • Would you rather be a firm manager or a happy-go-lucky one?
  • Would you rather maintain a professional demeanor or a friendly one for your team?
  • Would you rather employ a secretary or not?
  • Would you rather let a team member work at his one pace or should he adjust to your pace?
  • Would you rather manage a team remotely or in-office?
  • Would you rather manage a work-from-home team or an in-office team?
  • Would you rather lead a field team or an admin team?
  • Would you rather be an inspiration or a motivation?
  • Would you rather share your skill or just keep them to yourself?
  • Would you rather be creative in solving problems or stick to a set plan or matrix?
  • Would you rather send an email or talk to an employee in person?
  • Would you rather come in earlier than others or later than others?
  • Would you rather dress in a business suit or just a casual uniform?
  • Would you rather have your team wear their IDs or not?
  • Would you rather create a name for your team or not?
  • Would you rather monitor every move your team members do or just leave them on their own?
  • Would you rather give importance to your team members’ emotions or the company’s well-being?
  • Would you rather have direct contact with the owners or report to a senior executive?
  • Would you rather manage a sales team or an admin team?

Would You Rather Work Alone or as a Team Questions

Is the applicant a team player? Or more effective working as an individual contributor? Gain information about work style with these questions.

  • Would you rather work alone or with a team?
  • Would you rather work at home or in the office?
  • Would you rather work with a seatmate or by yourself?
  • Would you rather figure out the solution yourself or ask someone for help?
  • Would you rather team up with experts or learn as you go?
  • Would you rather have someone explain to you how things work or just figure them out yourself?
  • Would you rather have a sales partner or not?
  • Would you rather choose your own team members or have someone assign you a ready team?
  • Would you rather have a team outing or not at all?
  • Would you rather participate in team party activities or just sit in the corner?
  • Would you rather have a team party or none?
  • Would you rather go alone or with a team?
  • Would you rather solve problems alone or with input from your team?
  • Would you rather do the paperwork alone or with assistance from your team?
  • Would you rather trust your intuition or listen to your tea