Jane Scudder

We’ve all been there — you discovered your *dream job,* found a creative way to apply, connected with the recruiter, aced your phone interviews, and just know you are nailing the flurry of in-person interviews. But with 15 minutes left in your last interview, your would-be manager asks if you have any questions for her. You’ve already spoken with her for more than two hours at this point! You've asked all your questions and then some! You feel comfortable with the company! You want the role! But you don’t want to come across as dull and you want to use the time wisely. What do you say?!

Enter the fun interview question.

But what actually is appropriate to ask someone in an interview question and what’s not? Of course you know to avoid the truly off-limit topics of whether she’s thinking about starting a family or what her health is like, but what kind of question is both casual and fun yet appropriate?

The goal here is to avoid random questions and to keep the conversation professional. Instead of asking about their favorite song, favorite movie or what ice cream they like, you should keep the questions focused on professional life. An easy way to do that is to throw the “basics” back to the person on the other side of the interview table! Start with these four fun questions to ask and let the conversation go from there.

1. What were you doing before this role?

What she’ll get: People love talking about themselves. But because her team is clearly in a transitional state (you know this because they’re hiring!) she’ll appreciate the small space to reflect and she’ll feel more connected with you by being forced to consider the fact that we’re all carving out our own professional and personal paths.

What you’ll get: Insight to where she’s been, maybe some hints to the ups and downs of her career and whether or not you can trace any common threads. You don't want to ask an outright funny question, but you do want to know about this person's professional life and how they spent their time getting to where they are today.

Pro Tip: You want to operate with positive intent, but be on the lookout for anything from her professional past that raises a red flag to you. After all, an interview is a two-way street, so judge her answer the same way she's been judging yours.

2. Where do you see yourself in five years?

What she’ll get: Again, people love talking about themselves! And again, she’s in a transitional state whether she's conscious of it or not. This interesting question will give her the space to contemplate what’s next for her.

What you’ll get: Insight to what she wants and how she may be driving the team to position her for what she wants next. Also, since this might catch her off guard, you might get a more authentic, open answer — like something about her relationship with her boss or her biggest pet peeve. So listen up!

Pro Tip: Like the first question, you'll still want to operate with positive intent, but be tuned into whether she's satisfied with her current role or if "what's next" for her will actually be within the next three months. Just because she's interviewing you doesn't mean she's staying, so if she dodges a lot of personal questions about her future, take note.

3. What’s the best vacation you've been on recently?

What she’ll get: You're again touching upon everyone’s favorite topic (themselves!) but this one will also offer a moment where she can look at you as a human, not just an employee. How does your interviewer like to spend their free time? Do they spend most of their time with friends or with kids? This is an interesting question that will give you insight as to what kind of person your interviewer is, not just what kind of professional.

What you’ll get: Maybe you’ve been there too, or have always wanted to go. Or you’ll simply get insight to her interests and personal life in a way completely unrelated to work! Plus, this isn't just a random funny question, it will tell you about your potential boss' work-life balance — and what your work-life balance might become.

Pro Tip: If any of these feel awkward or too casual for you, use inflection, pacing and tone. This is something I stress in interview coaching — sit back, smile and say something like, “Gosh, at this point we’ve talked — what, for over 2 hours all in — I feel like I really see the role and company clearly, but I would love to know a bit more about you and your background. What were you doing before you took this role?” This strategy works for all of these: “…I would love to know a bit more about you — tell me, what’s the best trip you’ve gone on recently?”

4. Are you from [CITY X] originally?

What she’ll get: I don’t think I need to repeat the fact that people love talking about themselves. This fun icebreaker is always great to bring up because it's the opposite of a stupid question — not everyone has always lived in the place where they work! With this question, your interviewer will feel more connected with you and have a moment to think about her own past, not just yours.

What you’ll get: More insight to her and the potential to connect on something completely unrelated to work. Also, there’s something about where we’re all “from” that can really bring up interesting reactions.

Pro Tip: If the others don't feel right, try my favorite small talk question — ask someone where they’re from but framed in slightly different way. You know where she currently lives so rather than asking what can feel semi-stale ("Where are you from?"), ask if she's from that city. It also opens the door for her to share about any moves she’s made over the course of her life that you may relate to!

At the end of the day, an interview is just a conversation. The questions you ask and answers you give should be thoughtful and informative but don’t have to be staunch and dry! When you infuse fun and playfulness, you'll never know what you’ll learn. I often joke that I got my first job out of college because one of the executives on the team was also from New Jersey. I was qualified and it was the right fit all around, but having a kinship to this influential person certainly didn't hurt.

This is a small, funny world we live in so don’t shy away from asking seemingly small, funny questions here and there!


Jane Scudder is a certified coach, facilitator, and workplace & leadership consultant based in Chicago, IL (originally from NJ!) She helps individuals and group navigate their careers, teams, and personal lives. Find out more at janescudder.com.