Trivia Night Games: Why Most Aren’t Fun (And One That Is)

Written by:
Eli Robinson
Updated:
June 30, 2025

I was chatting with a project manager last week about trivia night games.

He had just stepped into her new role managing a remote team for the first time, and honestly, he sounded exhausted.

Not from the work itself, but from trying to figure out how to bring his people together when they were scattered across three time zones.

Yes, three!

He told me, "I tried a few trivia night games I found online, but it felt like I was hosting a webinar that no one wanted to attend."

That hit me. Because I’ve heard that exact same thing from so many others.

Why Trivia Night Games Can Feel Like A Letdown

Most trivia night games out there look good on paper.

You click into them expecting to spark some fun, and what you get is:

  • Clunky interfaces
  • Bland questions
  • Awkward silences

That’s not community-building. You're watching your team slowly disengage, one question at a time.

After it's all over, you wonder why you bothered setting up the game.

I’m often talking to team leads who feel the pressure to be the "culture person" on top of their actual job.

They want trivia night games to be this magical, low-lift solution to bring people together.

But when the software is clunky or the questions are forgettable, it just feels like one more item on a to-do list.

What Makes Trivia Night Games Work

What we’re seeing at Water Cooler Trivia is that great trivia night games come down to a few key ingredients:

  • The questions have to feel human
  • The format has to be simple
  • The timing has to match the energy of the team

If your team is slammed on Mondays, don’t hit them with a 25-question trivia session that morning.

If your team is more into pop culture than history, let that shape the questions.

We’ve found that when people feel like the trivia is made for them, not just made for "teams in general," they start to care.

They'll look forward to Monday morning quizzes and  message each other about who got which answer.

It goes from being a task to being a shared moment.

Writing For Real Teams

Whenever I’m building something new for Water Cooler Trivia, I picture the person on the other end of the quiz.

Someone who’s juggling deadlines, trying to keep their Slack inbox under control, and carving out five minutes to connect with their coworkers.

We have noticed that people don’t want trivia that tries too hard.

They want clever questions that make them smile or say, "Wait, I know this one."

They like getting results that start inside jokes and lead to unexpected shoutouts during the next Zoom call.

That’s why all of our quizzes at Water Cooler Trivia is written by actual humans who love trivia.

The weekly format keeps things consistent, but never boring.

And the customization options mean you’re never locked into a format that doesn’t fit your team’s vibe.

Adding A Personal Touch

I'm a big fan of the small moments that come from trivia night games done right.

When a quiet team member suddenly dominates a round about 90s sitcoms, or the finance team hilariously misspells an answer, and it becomes a running joke.

Or someone says, "That was the best part of my week."

That’s the real power of trivia. For us, it's about making work feel a little less like work.

Try It Free For Four Weeks And Thank Me Later

If you’re managing a team and you’ve been burned by trivia night games in the past, I get it.

But I also know how exciting it feels when you get this right.

That’s why we offer a four-week free trial of Water Cooler Trivia.

No sales calls or credit cards.

Just a chance to see what it’s like when trivia feels effortless.

Give your team a reason to smile on Monday morning.

Start your free trial today and see how different trivia night games can feel when they’re built with people in mind.