How Well Do You Know Your Coworkers? Fun Ways to Find Out

You spend more waking hours with your coworkers than with your family. You know their coffee order, their meeting style, maybe even their commute. But do you actually know them? Could you predict how they'd react in a crisis? Do you know what they did before this job, or what they'd do if they won the lottery tomorrow?

Turns out, most of us dramatically overestimate how well we know the people we work with. We know the professional version — the one who shows up to meetings and answers Slack messages — but miss the full person underneath. And that gap costs more than you might think.

Signs You Don't Know Your Team Well Enough

Before we get into the fun stuff, here's a quick reality check. You might not know your coworkers as well as you think if:

• You couldn't name three things they do outside of work
• You have no idea how they'd handle a stressful deadline (beyond "probably stress")
• You've never had a conversation that wasn't about a project or task
• You couldn't predict who the group would vote "most likely to start their own company"
• You don't know what they did before joining your company
• You've worked together for months but still feel like strangers

Sound familiar? You're not alone. Remote work, back-to-back meetings, and the general pressure to "stay professional" has made genuine connection at work harder than ever. But it doesn't have to stay that way.

Quick Test: How Well Do You Know Your Team?

Here's a simple exercise. Pick a coworker you interact with regularly and try to answer these questions without asking them:

Could you confidently answer more than half? If not, don't worry — that's exactly why you're here. The good news is that getting to know your coworkers doesn't require awkward forced conversations. The best approach is to make it fun.

Games That Reveal Who Your Coworkers Really Are

Structured play is the fastest way to learn about people. Games give permission to share things that would feel weird to announce in a meeting. Here are the best ones for uncovering who your team really is.

1. Most Likely To (The Group Perception Game)

Why it works: You don't just learn facts — you learn how the group perceives each person. It's a mirror that shows you what impression you're actually making on your team.

Everyone votes simultaneously on questions like "Who's most likely to survive a zombie apocalypse?" or "Who's most likely to have a secret talent?" Results often surprise people — sometimes you discover the quiet one is unanimously voted "most likely to become CEO."

The magic is in the discussion that follows each vote. When someone gets unanimously voted "most likely to negotiate their way out of anything," stories start flowing. "Remember when you talked us into that budget increase?" Suddenly you're not just coworkers — you're people with histories.

2. Two Truths and a Lie (The Surprising Facts Game)

Why it works: People share things they'd never mention otherwise. The game format gives permission to brag, confess, and reveal.

Each person shares three statements about themselves — two true, one false. The group votes on which is the lie. The best players make their truths sound unbelievable and their lies sound mundane.

You'll discover that the accountant was a competitive breakdancer. That the quiet developer has visited 40 countries. That your manager once worked as a professional dog walker. These revelations completely change how you see people.

3. Would You Rather (The Values Revealer)

Why it works: Hypothetical dilemmas reveal priorities, fears, and what people actually care about.

Pose questions like "Would you rather have unlimited vacation but always work weekends, or fixed vacation but never work weekends?" Watch the room divide. The conversations that follow reveal work styles, life priorities, and values — without anyone having to directly share their "values."

4. Team Trivia About Each Other

Why it works: Tests existing knowledge while creating memorable new associations.

Before the game, collect one unusual fact from each team member (via anonymous form). During the game, read facts aloud and have the team guess who it belongs to. "This person was once a licensed pilot" — watch as everyone reevaluates their assumptions.

The guessing is fun, but the real value is in the reveals. Each fact becomes a conversation starter for months afterward. "Hey, you were a pilot — what was that like?"

Questions to Ask to Get to Know Coworkers

Not every team bonding moment needs to be a structured game. Sometimes a good question at lunch or during a 1:1 can do the trick. Here are questions that go beyond "how was your weekend" without feeling invasive.

Easy Starters (Low Vulnerability)

• What's the best thing you've watched/read lately?
• What's your go-to productivity hack?
• What did you want to be when you were a kid?
• What's the most useful thing you own under $50?
• Coffee, tea, or something else entirely?
• What's your ideal vacation — adventure or relaxation?

Going Deeper (Medium Vulnerability)

• What's something you're weirdly passionate about?
• What's a skill you'd love to learn but haven't yet?
• What's the most interesting job you've ever had?
• What would you do if you had a year off with full pay?
• What's something people are usually surprised to learn about you?
• How did you end up in this field?

For Teams That Already Know Each Other Well

• What's your biggest unpopular opinion?
• What's the best piece of advice you've ever received?
• What's something you've changed your mind about in the last few years?
• If you could go back and give your younger self one piece of career advice, what would it be?
• What's a problem you wish someone would solve?

Making Coworker Connection a Habit

One team-building event won't transform your workplace relationships. The magic happens when learning about each other becomes woven into how you work.

The teams that know each other best didn't get there through a single offsite. They built connection gradually, through hundreds of small moments. A question here, a game there, a genuine conversation when they could have just talked about work.

The Remote Team Challenge

If knowing coworkers is hard in an office, it's brutal remotely. You don't get the kitchen chats, the overhearing of personal calls, the accidental discoveries that happen when humans share space.

Remote teams have to be intentional about what in-person teams get for free. That means:

• Scheduling social time — it won't happen organically
• Using video — faces matter for building connection
• Playing games that work online — voting games, trivia, and discussion games translate well
• Creating informal channels — Slack channels for pets, hobbies, or random thoughts
• Meeting in person occasionally — even once a year makes a huge difference

For more ideas, see our guide to virtual party games for remote teams.

What Knowing Your Coworkers Actually Changes

When you really know the people you work with, everything shifts:

• Communication improves. You know who needs details vs. headlines, who processes out loud vs. internally, who needs deadlines vs. flexibility.
• Conflict becomes easier. Disagreements feel less threatening when you know the person behind the opposing view isn't an adversary.
• Collaboration flows. You know who to loop in for what. Who's the creative thinker? Who spots risks? Who executes flawlessly?
• Work becomes more enjoyable. Showing up to a job where people know and appreciate you is fundamentally different from showing up to a place full of strangers.
• Retention increases. People don't leave jobs; they leave situations where they feel unseen. Being known is a reason to stay.

The ROI of knowing your coworkers isn't just warm feelings — it's better work, faster communication, and teams that stick together through hard times.

Frequently Asked Questions