Fun onboarding questions for new hires

“What is your dream vacation?”

“What game or movie universe would you most like to live in?”

“If you didn’t have to sleep, what would you do with the extra time?”

“What is the oldest thing in your refrigerator?”

Do these types of questions sound like something out of a dating mixer for singles or perhaps a quiz in a lifestyle magazine? They are fun, potentially insightful, and perhaps very useful to your company’s onboarding process.

Interview Bootcamp D

Smart employers know that structured, thoughtful onboarding experiences lead to better employee retention rates. Learning more about new hires during this impressionable period helps them to feel welcome. They start to feel the company values them as individuals, not just as paid workers.

Starting a new role is a stressful time. Nerves run high. Breaking up paperwork and presentations with something enjoyable provides a welcome respite. From day one, new employees start thinking about whether or not they made a good decision in taking their position. Smiling, laughing, and camaraderie during onboarding leaves positive memories.

Gathering information

Obviously, tossing thought-provoking questions out of the blue comes off as rather strange. (“Fill out your medical benefits enrollment form. Then, think about which fictional movie character you identify with the most.”) Rather, integrate them in ways that make sense.


Consider presenting a premade list of around 10 interesting questions. New hires can fill it out just like they would other onboarding documents. Make it clear that the questions are a fun way for the company to learn more about new employees. Assure that questions can be skipped or info not shared if desired.

If a group of new employees are onboarding together, the human resources leader may want to devote some time to people sharing their answers. This breaks up the monotony of onboarding and provides an opportunity for new hires to connect. Learning, say, what others remember as their favorite childhood toy can spur memories and lively discussion.

Giving managers a copy of the filled-in questionnaire also can be worthwhile. Leaders can examine it to better know their direct charges. Answers give something unique to talk about during one-to-one meetings.

Icebreaker game

Some organizations use questions in social situations to get co-workers talking. Put questions on individual slips of paper and gather them in a hat. Team members, including the new person, take turns drawing and answering. Comments and conversation are bound to flow. (Imagine the possible number of answers to something like “If your house were on fire, what non-living possession would you save first?”)

Buddy conversation

Companies frequently pair a new person with a mentor or onboarding buddy. Give the duo a list of engaging questions to spur conversation at their first meeting. A lunch spent reminiscing about childhood pets or discussing which animated movie each has seen the most times will ease awkwardness.


Have an internal publication? Feature a picture of new hires along with responses to questions such as “What is your most prized collection?” or “What food do you find most addicting?” Sandra becomes more than just the new receptionist. She is a person with 55 Yoda figures who can’t get enough sour pickle potato chips. Jim from accounting seeks her out with pictures of his prized original Star Wars action figures. Julie from marketing remarks that she’s never tried that flavor chip but will soon. Let the team building begin!


Some work environments ask new team members (including remote employees) to come up with a short PowerPoint or other type of introduction. Many new hires run with the creative opportunity. Others need more help. They benefit from a template that includes interesting, open-ended questions they may wish to address. Telling the group your all-time favorite movie quote or your celebrity crush at age 13 is a fun way to show some personality.

What to ask

Questions posed to new employees run the gamut. Stay away, though, from anything too personal or revealing. (Subjects such as religion and politics remain too sensitive for the office.) A main purpose is to help the person relax and begin feeling part of company culture. The last thing you want is an uncomfortable interrogation.

Many leaders work on constructing fun questions that also provide insight. Actively listening to answers can give clues into things such as accomplishments, motivators, needs, and styles.

Dan Belcher, founder and CEO of Short Sale RE, states that “digging into these questions during onboarding gives us a cool glimpse into who someone is.” Questions he likes to cover include:

What superpower would you pick if you could have one?

“It opens up this window into their dreams and what they’re all about,” Belcher says. “It’s not just daydreaming stuff; it helps you understand their values and what drives them.”

What is your proudest work moment?

“Finding this out goes beyond the usual chit-chat. It’s like giving props for their hard work and letting them share their achievements. It’s not just formalities; it’s a way to see their skills, work ethic, and what they’re all about professionally.

What is your ideal pet?

“That’s a fun way to explore their quirks. It’s not just random; it shows what qualities they dig in a pet, giving you a more rounded picture of who they are. It’s the little things that make onboarding more interesting and connected.”

Percy Grunwald, personal finance expert and co-founder of Compare Banks, sees the onboarding process as “a crucial opportunity to not only gather essential information about our new employees but also to create a welcoming and engaging environment.” To break the ice and “foster a positive and inclusive workplace culture,” he incorporates questions such as:

If you could have dinner with any historical figure, living or dead, who would it be and why?

“This question provides insights into the employee’s interests, values, and even their communication style. It helps build a personal connection from the start and sets a friendly tone for their journey with Compare Banks. Additionally, the responses to this question often reveal aspects of creativity, critical thinking, and cultural awareness.”

If you were stranded on a deserted island and could only bring three items, what would they be?

“While seemingly whimsical, this question allows me to gauge a candidate’s ability to prioritize, think resourcefully, and perhaps showcase a bit of their sense of humor. It also opens the door for team members to share anecdotes or common interests, creating bonds beyond the professional realm.”

What’s one skill you possess that isn’t on your resume, but you believe adds value to our team?

“This question encourages employees to reflect on their unique strengths and talents, fostering a sense of individuality within the team. It also empowers them to recognize the diverse skills they bring to the table, creating a culture where everyone feels seen and appreciated for their contributions.”

Ritika Asrani, founder and head broker at St Maarten Real Estate, often includes these questions during onboarding:

What does your dream home look like?

“Inquiring about the key features of their dream home isn’t just a conversation starter; it’s a strategic move to unveil their problem-solving mindset. We’ve noticed that the features they prioritize often mirror their approach to challenges in the real estate realm. It’s a subtle but insightful glimpse into their professional thinking.”

What is your favorite book?

“While the favorite book question may seem standard, we’ve taken it a step further. We encourage employees to share not only their favorite books but also one that challenged their perspective. This deeper inquiry sparks discussions on adaptability, open-mindedness, and the ability to embrace diverse viewpoints – qualities we highly value in our collaborative environment.”

What activities do you enjoy outside of work?

“Beyond the usual hobbies, we delve into their extracurricular pursuits to uncover hidden talents. Whether it’s a penchant for culinary arts, a secret talent for photography, or a passion for sustainable living, we’ve crafted team-building activities that tap into these unique skills. It’s a way of celebrating the diverse expertise our team brings beyond their real estate roles.”

Learning about a new hire’s interests and background can help down the line. For instance, asking “What is the most memorable token of appreciation you’ve ever received in your career?” provides insight on recognition preferences. Some people are motivated by bonuses and other extrinsic rewards, while others prefer more personal expressions.

Similarly, leaders and co-workers can draw upon their knowledge of a person’s interests when choosing gifts for occasions such as work anniversaries. Hearing someone’s “all-time favorite piece of clothing” is a thread-bare Metallica t-shirt from a concert attended during college might lead to purchasing their greatest hits CD as a Secret Santa present.

Troy Port, director of operations at Studypool, includes this question during the onboarding process: What is your favorite flavor of ice cream? Guess what the team celebrates with at the end of the newcomer’s first month?

Keep the questions coming

Successful onboarding programs go well beyond the first day, first week, and even first month of a new job. The first three months are a critical time to build employee engagement. Show new hires that you remain interested in learning about them.

After the early days, though, the nature of your questions may shift. Instead of icebreakers, you may want to focus more on employee experience. This feedback assists in understanding the new worker’s adjustment, confidence level, and concerns.

Whether doing a check in or conducting a survey, though, remember that questions do not need to be boring. Interesting presentation or wording adds to interest level and enhances organizational reputation.

For instance, instead of a questionnaire where respondents simply hit the word “yes” or “no,” provide eye-catching visual choices, such as of a toddler vigorously shaking his head in agreement or refusal. Asking someone to rate the difficulty of a certain task? Create a scale going from “easy peasy lemon squeezy” to “harder than performing a root canal on yourself.”

Present plenty of open-ended questions, too. Ask what job duties they can’t get enough of and which they would gladly trade. See what they are most proud of accomplishing so far and what still stumps them. Inquire about work-life balance, favorite work moments, and what they have found most surprising about company culture. Welcome ideas and suggestions.

Lastly, seek employee feedback about the employee onboarding process. Going through it makes them first-hand experts on the subject. Find out their first impressions, what they enjoyed, where improvements could be made, and perhaps even their favorite piece of swag. This knowledge will help in making the experience better for future newcomers. You may even solicit ideas for new icebreaker questions to ask new hires!