April 30, 2025

Guess Who? Questions to Get to Know Your Coworkers (For Real)

Remember the “Guess Who?” board game from the ’80s and ’90s? You’d try to figure out your opponent’s secret character by asking a series of yes or no questions about their appearance. Stuff like, “Is your character wearing glasses?” or “Do they have rosy cheeks?” Every answer helped you narrow down the board until you could make your big guess, hopefully before they guessed yours. (Bonus points if you asked your questions in your best game show host voice.)

I was reminded of this nostalgic classic recently when I attended a talk with my nephew at his church youth group. The speaker referenced the “Guess Who?” game to get us thinking about how often we size people up based purely on looks. It’s wild how fast we can slap labels on people based on just what we see. We know we’re more than our outsides but it’s easy to forget. Especially in a culture that practically worships appearances, TikTok highlight reels, and poshly dressed celebrities.

It got me thinking: this whole surface-level snap judgment thing shows up at work, too. How well do we actually know our coworkers, like beyond their job titles and Slack profile pics? How much do our assumptions and unconscious biases sneak in and color the way we view, interact with, and even value other people?

So let’s dive into all the angles. And preview: I’ve got a solid list of questions to get to know your coworkers better coming your way!

You know what happens when you assume, right?

As the ancient wisdom (ok, middle school teachers) say: when you assume, you make an “a$$” out of “u” and “me.” 😝
Even if we want to believe we’re above judging by appearances, it’s sneaky. Without even realizing it, we can form opinions about people’s abilities, intelligence, experience, or work ethic based on things like how they dress, how young or old they look, or how outgoing they are. And when we’re not tuned into our biases, that’s what’s known as unconscious bias.

These hidden assumptions can quietly mess with workplace dynamics, potentially causing us to…

• Exclude people from projects without realizing it
• Stop listening as actively to certain people
• Show favoritism to some coworkers over others
• Talk over others or shut them down in conversations
• Overlook someone’s ideas
• Miss out on diverse perspectives
• Stick to surface-level, transactional conversations
• Erode team morale and trust

Plus, it can just make work feel a lot lonelier and less meaningful for everyone.

Why it’s worth going beyond the surface

When you take the time to get to know your coworkers beyond the “small talk and status updates” level, good stuff starts to happen.

Real connection = actual trust.
Actual trust = better collaboration.

When people feel truly seen at work, they’re more likely to:

• Share their real ideas (even the weird but genius ones)
• Give and receive honest feedback
• Take more risks
• Put in greater effort
• Support coworkers more often
• Stick around longer
• Be more creative
• Reach out to others to collaborate
• Actually enjoy working with you

So when there’s not genuine trust and connection, teams get stuck in fake-friendly mode. Lots of “how was your weekend?” and “good, you?” but not much else. Issues don’t get addressed, ideas don’t get shared, and suddenly everyone’s Googling “How to get rid of the Sunday scaries.”

Now, quick caveat:
Building stronger connections doesn’t mean you have to turn every coworker relationship into BFF territory. In fact, getting too buddy-buddy can cause its own set of problems: favoritism, blurred lines, lack of accountability, and drama that belongs on “The Real Housewives,” not your project team.

It’s about balance: being human, being open, while still keeping things professional and respectful. And remember, you can invite deeper conversations, but you can’t force someone to open up if they’re not ready.

Topics that help you go deeper

If you’re wondering what to even talk about beyond work projects and weekend weather, here’s your starter kit:

• Hobbies and interests
• Hidden talents (bonus if it’s juggling or speaking fluent Klingon)
• Strengths (like, have they taken one of those nifty strengths assessments?)
• Core values and priorities
• Past jobs and career stories
• School or education experiences
• Important family members or mentors
• Life challenges they’ve overcome
• Favorite books, shows, movies, or podcasts
• Travel adventures (or dream destinations)
• Personal goals or bucket list dreams
• New things they want to learn

The key: Ask open-ended questions

In “Guess Who?,” you ask close-ended yes/no questions because you’re trying to eliminate options fast.
In real life? If you only ask yes or no questions, you’ll make it hard to keep a real conversation going. Instead, go for open-ended questions. Ones that start with what or how. They open the door for real stories, insights, and connection.

Questions to get to know your coworkers

Here’s a whole buffet of open-ended questions to get to know your coworkers better:

• What do you enjoy most about the work you do?
• How did you get into your current field?
• What’s a career moment you’re especially proud of?
• What activities or sports did you enjoy growing up?
• What’s a toy or hobby you were obsessed with as a kid?
• How do you like to spend your free time these days?
• What’s your favorite way to kick back after a busy week?
• If you had a free Saturday afternoon, what would you choose to do?
• What are you nerding out about lately?
• What’s something you’re excited to achieve this year?
• How has your career path surprised you so far?
• What’s a hidden talent you have that most people don’t know about?
• What’s a book, podcast, or show you’re really into right now?
• What kind of music do you listen to the most?
• What’s one place you’ve traveled to that you’d recommend to everyone?
• If you could go on a dream vacation, where would it be?
• What’s something you’re curious to learn more about?
• What’s a challenge you’ve overcome that shaped you?
• How do you define success in your own life?
• What’s a piece of advice that’s stuck with you?
• What’s one of your biggest values or priorities right now?
• Who’s an important person in your life who’s really impacted you positively?
• Who’s been an influential mentor for you?
• What have you learned from any of those personality or strength assessments?

Bottom line?

We’re all more than just “glasses” or “rosy cheeks” (or that one guy with the epic mustache in “Guess Who?”). Ask better questions to get to know your coworkers. Get curious. Connect for real. Your team and your workplace will be way better for it.