When I first stepped into the role of interviewing job candidates, everything felt like a set routine. I’d greet someone with a polite smile, ask them about their professional background, then nod while they repeated the usual buzzwords. After a while, I realized that, while I was gathering valuable facts about their experience, I wasn’t seeing much of their true personality. I wanted to know if this person would actually mesh well with my existing team. The more interviews I conducted, the more I noticed that a few standard questions simply weren’t enough to capture someone’s spark.
That’s when I decided to experiment with questions that veered a little off the conventional path. I remember the first time I asked a candidate a playful, unexpected question right after going through the mandatory “Tell me about your responsibilities in your last position.” It was something along the lines of, “If you could have any superpower for a day, what would it be?” I saw their eyes widen for a second—then they broke into a big grin and launched into an animated explanation of how they’d use telepathy to better understand co-workers. I still got to see their communication style and thought process, but in a more natural, unscripted way.
As I added more of these offbeat questions to my interview toolkit, I noticed that candidates began to relax. Instead of feeling as though they were reciting facts for an exam, they treated our conversation more like a chance to genuinely connect. The entire vibe shifted. People who might have been nervous felt free to be themselves, which often revealed a creative or humorous side I wouldn’t have discovered otherwise. Of course, I still needed to confirm their qualifications, but sprinkling in one or two fun prompts gave me deeper insights into how they approached problem-solving and how they might get along with a group of equally motivated, curious co-workers.
I started to see that these imaginative questions also helped me gauge how a candidate thought on their feet. Traditional interview questions often allow for rehearsed answers, but something playful and off-topic tends to catch people by surprise. Their response speaks volumes about how they handle unexpected situations, a quality I found incredibly valuable in roles that require adaptability. For instance, I once asked a developer how many tennis balls could fit into the office. Even though the actual number wasn’t important, I was struck by how meticulously this person began mapping out the room in their mind, calculating its rough volume, and factoring in the space that tennis balls would leave when stacked. That little exercise told me a lot more about their logical thinking than any standard “describe your technical skills” query.
There was, however, a delicate balance to strike. When I first began experimenting, I got a bit carried away and turned entire interviews into playful Q&A sessions. Eventually, I realized that too many lighthearted questions could distract from the main purpose: determining if a candidate truly met the job requirements and if they were a cultural fit for the team. It helped me to weave these fun prompts in between the more substantial questions, so I could still gather the essential details about a candidate’s background without sacrificing the benefit of spontaneity.
Over time, I also learned the value of reading the room (or the Zoom). Not everyone is comfortable with on-the-spot creativity. If I noticed someone freezing up or struggling to respond, I’d offer them a moment to think it through, or I’d pivot to something less intimidating. The last thing I wanted was to make a candidate feel ridiculed. The goal was always to spark authenticity, not create an awkward game-show moment.
Yet, I found that these fun moments often paved the way for more engaging, memorable interviews. They allowed me to see if someone had a sense of humor, a collaborative spirit, and a willingness to embrace the unexpected. I remember one interviewee who was initially reserved until I asked about the most unusual hobby they’d ever tried. They lit up and told me a hilarious story about experimenting with competitive dog grooming—an odd pastime, but one that revealed their adventurous side. That short anecdote told me they wouldn’t be afraid to tackle unique challenges or step out of their comfort zone at work.
Naturally, I kept in mind that not all playful questions were relevant. Whenever I considered introducing a new prompt, I asked myself what insight I was hoping to uncover. Sometimes, people think it’s fun to quiz a future programmer on their favorite ice cream flavor, but if the goal is to see how they’d integrate with a design team or communicate with non-technical colleagues, that question might not offer much. It was always best to align each playful twist with something meaningful, like creative thinking, stress management, or overall enthusiasm.
Eventually, I came to appreciate just how much these moments of levity enriched my interviews. I still made sure to cover the essentials about experience, achievements, and professional goals. But by folding in a few imaginative prompts, I felt like I got a much clearer picture of how these candidates would actually act on the job, especially when faced with surprises or asked to work in groups. Even the candidates themselves often left with smiles on their faces, telling me they appreciated an interview that stepped beyond the typical, robotic Q&A.
Over the years, I’ve talked with plenty of colleagues who remain skeptical of “fun questions,” worried they’ll make the company look unprofessional or frivolous. But in my experience, a well-placed creative twist shows that you care about more than just ticking boxes. You’re curious about the human side of each applicant, and you’re ready to offer a work environment where new ideas are welcome. That’s the real reason to weave a little fun into your interviews: you get a better sense of the person behind the résumé, and they learn you’re the kind of team that values open-mindedness. After all, in a hiring climate where top talent can afford to be choosy, showing genuine interest in who candidates really are can be a significant advantage—and a more enjoyable way to meet your next star team member.
Alex
