Here is a list of creative and exciting games you can enjoy with your boss.
Each game is easy to set up and fun to play. They are also great for testing knowledge in a light and friendly way.
Pick the ones you like most and bring some energy into your workplace.
“Explain It Like I’m 5”
Ask your boss to explain a complex company concept or strategy in the simplest possible terms.
Pick a hard topic from your company or work. It could be a product, a strategy, or a process.
Ask your boss to explain it as if they were talking to a 5-year-old. They must use very simple words and short sentences.
No big jargon. This game is fun because it tests whether they can make complex ideas easy for anyone to understand.
Buzzword Bingo
Create a bingo card with industry buzzwords. Each time your boss uses one during a meeting or game, you mark it. Bonus: ask them to define each.
Make a bingo card with common work buzzwords.
These are fancy or trendy words people use in meetings, like “synergy” or “pivot.” Every time your boss says one, you mark it on your card.
You can also ask them to explain what the word really means. This is a light and playful way to see if your boss truly knows the meaning behind the words they use.
What Would You Do? (Scenario Game)
Present hypothetical business crises or dilemmas and ask how they would handle them.
Think of a pretend problem at work. It could be a big client leaving, a project going wrong, or a computer crash.
Tell your boss the problem and ask, “What would you do?” They must quickly share their plan.
This game shows how they think in a tough moment. It also helps the team learn good problem-solving skills in a safe and fun way.
Stump The Boss
Employees prepare niche questions about the industry or company history and try to stump the boss.
Everyone on the team makes tricky questions about the company or the industry.
These should be things only a real expert would know. Take turns asking your boss.
If they cannot answer, you get a point.
This game is fun because it challenges the boss’s memory and knowledge. It can also help the team learn cool and surprising facts about the business.
Let the team ask the boss tough job interview questions they’d normally ask candidates.
In this game, the boss becomes the candidate, and the team becomes the interviewers.
Ask them the same tough questions you would ask a new hire. Questions can be about skills, past work, or how they solve problems.
This game is funny and also shows how the boss thinks under pressure. It can make the team feel closer to the boss, too.
Trivia Duel
Pick categories like “tech,” “finance,” “sports,” “pop culture,” or “company trivia” and go head-to-head.
Choose some topics for a trivia battle. It could be about technology, sports, movies, world facts, or company history.
You and your boss take turns answering questions. You can keep score to see who wins. This game is simple but exciting.
It shows what random facts your boss knows and is a good way to mix work talk with fun competition.
Two Truths and a Lie: Career Edition
The boss shares 3 statements about their career; team guesses the lie.
The boss says three things about their career. Two of them are true, and one is made up.
The team has to guess which one is the lie. This game is fun because it mixes truth, surprise, and a little mystery.
It can also help everyone learn more about the boss’s career in a playful way.
Who Knows The Team Better?
Boss answers personal trivia about their direct reports (favorite food, alma mater, etc.).
The boss tries to answer personal trivia about each team member.
It could be their favorite food, the school they went to, or a hobby they enjoy. The game shows how well the boss pays attention to the people they work with.
It can be funny and sweet when the boss guesses wrong in silly ways.
Quick Facts Showdown
Fire rapid-fire questions in a timed format. Topics can range from global affairs to business leaders.
This is a fast and exciting game. Ask the boss quick questions one after another, without giving them much time to think.
Questions can be about world events, famous people, history, or company facts. The goal is to answer as many as possible before time runs out.
It tests how fast the boss can think and recall information.
Acronym Blitz
Test how many industry acronyms your boss can decode (e.g., SaaS, ROI, CAGR).
Make a list of acronyms that are used in your industry or company. Examples could be SaaS, ROI, or CAGR.
Read them out one by one. The boss must say what each one means. You can set a time limit to make it harder.
This game is a quick way to test your boss’s knowledge of important terms in the business.
Spot the Lie (PowerPoint Edition)
Create a deck with real and fake company data; see if the boss can spot the false info.
Create a short PowerPoint with company numbers, charts, and facts. Some of them should be true, and some should be fake.
Show it to the boss and ask them to point out the false ones.
This game tests how closely they know the company’s real data. It can also be a fun way to review business updates.
The Logic Puzzle Race
Present logic puzzles or riddles to see how quickly your boss solves them.
Give the boss a logic puzzle or a riddle to solve. You can find ones with patterns, clues, or tricky word problems.
Time them to see how fast they can figure it out.
This game is a fun brain workout and shows how well your boss thinks under pressure. It works well for team challenges, too.
Guess the Chart
Show anonymized charts (sales, traffic, etc.) and ask what they likely represent.
Show the boss a chart or graph, but remove the labels and titles.
It could be about sales, website visits, or any kind of data. Ask them to guess what the chart is showing.
This game tests how well they recognize patterns and trends in numbers.
It’s also a fun way to see how much they know without all the clues.
What’s Missing?
Present a process flow or organizational chart with missing parts and ask them to identify the gaps.
Create a picture of a process flow, checklist, or organizational chart.
Leave out one or more important steps or people. Show it to the boss and ask them to find what’s missing.
This game checks how carefully they understand the company’s systems. It also encourages quick thinking and attention to detail.
Pitch a Product (Shark Tank Style)
Boss is a contestant and has to pitch a silly product using real marketing strategies.
In this game, the boss pretends to be a business contestant.
They have to pitch a funny or silly product idea to the team. The twist is that they must use real marketing and sales strategies to make it sound amazing.
This game mixes creativity with business skills and can lead to lots of laughs.
Role Swap
Boss and employee switch roles and solve a problem from the other’s perspective.
In this game, the boss and an employee switch roles.
The boss pretends to be the employee, and the employee pretends to be the boss. Then you give them a problem to solve from that point of view.
This is a fun way to see how well they understand each other’s jobs. It can also build empathy and teamwork.
Would You Rather: Leadership Edition
Pose tough leadership dilemmas like “Would you rather lose your top performer or top client?”
Ask the boss a series of “Would you rather” questions that are about leadership.
For example, “Would you rather lose your top performer or your top client?” These are tricky questions with no easy answer.
This game shows how the boss makes tough choices. It can also start interesting discussions with the team.
Metaphor Master
Give them a random word (e.g., “volcano”) and they have to relate it to the company or a leadership trait.
Give the boss a random word, like “volcano” or “parachute.” They must quickly connect it to the company or a leadership idea.
For example, they might say, “A volcano is like our sales team – it builds pressure and then explodes with energy.”
This game is fun, creative, and shows how well the boss can think on the spot.
Leadership Jeopardy
Create a custom Jeopardy game with categories like “Company Lore,” “Boss Moments,” and “Leadership Wins.”
Make a Jeopardy-style game with categories related to your workplace.
Examples could be “Company Lore,” “Boss Moments,” or “Leadership Wins.” Prepare questions for each category with points.
The boss picks a category and tries to answer correctly. This game is fun, competitive, and a great way to test how much the boss remembers.
Office Feud
Like Family Feud but with company-related or industry-specific survey questions.
This is like the TV show Family Feud, but with work-themed questions.
Ask the team survey questions, like “Name something people do in meetings.” Collect the top answers. Then have the boss guess the most common ones.
This game is exciting, full of laughs, and shows how well the boss understands everyday office life.
Who’s the Expert?
Team members pretend to be experts on random topics; the boss must guess who is faking and who actually knows.
Each team member pretends to be an expert on a random topic.
Some will be telling the truth, and some will be making it up. The boss asks them questions to figure out who is real and who is faking.
This game is playful and also shows how well the boss can read people and spot clues.
Conclusion
Playing games with your boss can make work feel lighter and more connected.
These activities are not only fun but also a smart way to learn new things about each other.
They can help build trust, improve teamwork, and even spark new ideas. Whether it’s a quick trivia round or a creative challenge, the goal is to enjoy the moment together.
Remember, the best games to play with boss are the ones that bring smiles and encourage everyone to join in.
So pick a few from this list, gather your team, and start making workdays more exciting.
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We’d love to hear from you!
Have you ever tried any of these games to play with your boss in your workplace? Which ones made everyone laugh the most, or brought the team closer?
Share your favorite ideas or funny stories in the comments.
