Riddles for Work – 40 Clean Riddles With Hidden Answers

How it works

These riddles for work are 40 old riddles picked for a meeting or a team chat: clean, quick to read aloud, and each with its answer hidden until you tap Show answer.

Read the full guide

Open a meeting with one

Read the riddle out and give the room a minute before you tap Show answer. Brain teasers suit a longer warm-up; Quick laughs suit a first slide or a chat channel. The page also keeps one riddle of the day, the same for everyone, so a team can share today's work riddle.

Where the riddles come from

Each one is in an old riddle or puzzle book, free to read at Project Gutenberg and named under the full list, and we told it again in plain words. We left out drink, romance, politics, religion and anyone's looks, so these are work appropriate riddles for any team.

Tips

On a video call, paste the riddle in the chat and ask for typed answers before anyone unmutes.

Questions and answers

What are good riddles for work meetings?

Short ones with one clear answer. Try "What grows bigger the more you contract it?" (debt) or the twenty-six sheep teaser. Set the count to 5 for a quiz round, and keep the full list, which is an answer key, off the shared screen.

Are these funny work riddles clean?

Yes. The laughs are puns, where the answer turns on a word with two meanings, such as a sheep pen. No riddle here jokes about a nationality, a job or a person.

Where are the work riddles with answers?

Tap Show answer under a riddle, or scroll to the full list below the tool: it prints all 40 riddles with each answer beside it. Brackets spell out the word play, as in ceiling whacks (sealing wax).

All 40 riddles

Desk and office 12

How do you punctuate this: I saw a five-dollar bill on the street? Make a dash after it.
If you bump your head on the ceiling, what office supply do you get? Ceiling whacks (sealing wax).
What does a packet of pins give you? Plenty of good points.
What does an envelope say when you lick it? Nothing. It just shuts up.
Which pen is never used for writing? A sheep pen.
Why is a bad joke like a blunt pencil? Neither one has a point.
Why is a bank clerk always well informed? They are always taking notes.
Why is a careful person like a pin? Their head stops them from going too far.
Why is a pencil like a stubborn child? It never does write (right) by itself.
Why is a watch so modest? It always keeps its hands in front of its face.
Why is an account book like a sculptor's studio? Both are full of figures.
Why is paper like a beggar? Both are made of rags. Old paper was made from rags.

Money and business 13

How do little fish go into business? They start on a small scale.
If all the money in the world were shared out equally, what would each person get? An equal share.
What grows bigger the more you contract it? Debt.
What is a good way to make money fast? Lock it in a safe deposit box.
What is the difference between a new nickel and an old quarter? Twenty cents.
What is the height of folly? Spending your last dollar on a purse.
What kind of tune does everybody enjoy most? A fortune.
When is someone completely immersed in their business? When they give swimming lessons.
Which fruit is on every penny? A date.
Which is worth more, a five-dollar bill or five gold dollars? The bill. Put it in your pocket and you double it; take it out and you see it in creases.
Why is a blacksmith never happy with the pay? He is always striking for wages.
Why is money so often damp? It is due in the morning and missed at night.
You lose a dollar today. Why lose another one tomorrow? To make your loss a gain (again).

Brain teasers 10

A farmer borrows a sack of wheat 6 feet round and repays two sacks 3 feet round, just as tall. Is that fair? No. The two small sacks hold only half as much as the big one.
A farmer had twenty-six sheep and one died. How many were left? Nineteen. Say it aloud: twenty sick sheep, and one died.
A hen and a half lays an egg and a half in a day and a half. How many eggs do 21 hens lay in a week? 98. One hen lays one egg every day and a half.
A man bought two fish. When he got home he had three. How? He had two, and one smelt.
How many cows' tails would it take to reach from Boston to New York? One, if it were long enough.
How much earth is in a hole 3 feet wide and 6 feet long? None. A hole is empty.
If a bicycle has two wheels and a tricycle three, what has five? A V-hicle.
What number of three figures, multiplied by 8, makes exactly 10? 1.25.
Which is heavier, a pound of feathers or a pound of gold? The feathers. Gold is weighed by the troy pound, which is lighter than the everyday pound.
Who can see more: a person with one eye or a person with two? The one with one eye. They see the other person's two eyes; the other sees only one.

Quick laughs 5

How many of your relatives live on your property? Ten aunts (tenants).
If a spider were late for dinner, what would it do? Take a fly.
If a tree broke a window, what would the window say? Tree-mend-us!
What is put on the table and cut, but never eaten? A deck of cards.
When does a chair dislike you? When it can't bear you.

How this list was compiled

Traditional riddles found in 4 public domain books on Project Gutenberg: The Handbook of Conundrums (Edith B. Ordway, 1915) https://www.gutenberg.org/ebooks/32898; How to Solve Conundrums (1900) https://www.gutenberg.org/ebooks/44099; Conundrums, Riddles and Puzzles (Dean Rivers, 1903) https://www.gutenberg.org/ebooks/52598; The Twentieth Century Standard Puzzle Book (A. Cyril Pearson) https://www.gutenberg.org/ebooks/63884. Book texts fetched from https://www.gutenberg.org/cache/epub/<id>/pg<id>.txt on 2026-09-24, and a script found the key words of every riddle and answer in one passage of its cited book (the line number is kept in x.line). Every riddle and answer was then told again in plain words for this page. Chosen for a workplace: nothing about drink, romance, politics, religion, death or anyone's looks, and none of the 173 riddles on this site's riddle-generator page. Licence: public domain sources (Project Gutenberg, https://www.gutenberg.org/policy/permission.html); the wording of each riddle and answer is own work