Online Tool Store
Random Question Generator
Generate random icebreaker, would-you-rather, retrospective, and writing-prompt questions from 108 curated picks, with no repeats until each set is used up.
🔒 This tool runs entirely in your browser. Your files are never uploaded to a server.
One question per line. Your list is saved only in this browser.
Recent questions
How to use it
- Tick the built-in categories you want, or save your own questions and select My questions.
- Choose how many questions to see at a time.
- Press for new questions as often as you like — none repeats until the bag empties.
- Review the recent-question history, then copy the current list if you are putting it into an agenda.
Why random picking feels broken
The obvious way to build this is to pick a random question each time you press the button. It repeats far sooner than anyone expects, and the maths is the same as the birthday problem:
pool of 18 questions, picked independently
after 5 picks 45.6% chance of a repeat
after 10 picks 95.6%
50% chance of a repeat by the 6th question
A coin flip that you see a duplicate by the sixth question is not a bug in the random number generator — it is what independent draws do. But to anyone using the tool it looks like the same handful of questions keeps coming up, which is the most common complaint about generators of this kind.
A bag, not a dice roll
So each category here holds a bag. It is shuffled once with Fisher–Yates, questions are dealt off the top, and the bag is refilled only when it is empty — the way a bingo cage works, or the way a well-designed music shuffle does. Every question in a category appears before any of them repeats, and the counter under the buttons shows how many are left.
The difference over a whole set is stark. Independent picking follows the coupon-collector problem, which needs about n × (1 + ½ + ⅓ + … + 1/n) draws to see everything:
to see all 108 questions at least once
picking at random ≈ 569 draws
dealing from a bag 108 draws
Five times the work for the same coverage. The shuffle itself uses the browser's cryptographic random source with rejection sampling, so no question is quietly favoured over another by the arithmetic used to pick it.
Two ways to mix categories, and why you get the choice
When more than one category is ticked, something has to decide which one the next question comes from, and there are two defensible answers that give different results:
even split each category equally likely
per question each question equally likely
with a 40-question and a 20-question category ticked:
even split 50% / 50%
per question 67% / 33%
Most tools pick one silently. All six categories here hold eighteen questions, so the two settings currently behave identically — but tick a subset with different sizes and the difference is real, which is why the switch is visible rather than buried.
What is in each set
Icebreakers are light and safe with strangers. Deeper conversation assumes some existing trust and will not suit a first meeting. Would you rather forces a choice, which is often more revealing than an open question. Team retrospective is written for sprint reviews and post-mortems, and leans on specifics rather than feelings. Writing prompts give a situation rather than a plot, which leaves the interesting decisions to you. Family and kids is aimed at the dinner table and works for a wide age range.
FAQ
Why do other generators repeat themselves so quickly?
Because they pick a fresh random question every time, which allows repeats immediately. From a pool of 18 there is a 46% chance of a repeat within five questions and a 96% chance within ten. It feels broken long before it is unlikely.
How does this one avoid that?
Each category holds a bag. The bag is shuffled once, questions are dealt from it, and it is only refilled when it runs out. So you see all 18 in a category before any of them comes round again — the same principle as a bingo cage rather than a dice roll.
What is the difference between the two weighting options?
With an even split, each ticked category is equally likely regardless of size. With every question equally likely, a category holding twice as many questions comes up twice as often. All six categories here happen to hold 18 questions, so the two behave identically — the choice matters if you tick a subset and the sizes differ.
How many questions are there?
One hundred and eight: six categories of eighteen. Drawing purely at random, you would expect to need around 569 draws to see all 108 at least once. Dealing from a bag gets you there in 108.
Can I use these in a workshop or a meeting?
Yes — the retrospective set in particular is written for that, and the copy button gives you a plain numbered list to paste into an agenda. Nothing here is licensed or tracked.
Is anything I do here recorded?
Your generated history stays in the current page session. If you save custom questions, that list is stored only in this browser so it is available next time. Nothing is sent anywhere, and there is no account.
Can I use this for team building or icebreaker games at work?
Yes — tick the Icebreakers or Team retrospective sets, both written for that use. It works for remote standups, workshops, and in-person team building sessions, and the copy button gives you a plain list to paste into meeting notes.
How many questions can I generate at once?
Choose 1, 3, 5, or 10 questions per round from the count selector above the buttons. The recent-questions list below keeps your last 12 draws for the session.
How we compare
| Feature | Online Tool Store | Other question generators | A printed card deck |
|---|---|---|---|
| No repeats until the set is exhausted | ✓ | ✗ | ✓ |
| Shows how many are left | ✓ | ✗ | You can see the pile |
| Mix categories, with the weighting your choice | ✓ | ✗ | Shuffle two decks together |
| Copy a numbered list into an agenda | ✓ | Sometimes | ✗ |
| Free, no account, no ads | ✓ | ✗ | Costs money once |
| Add and reuse your own questions | Yes | Sometimes | Write on a blank card |
| Recent question history | Included | Varies | Keep your own notes |
| Works with no screen in the room | ✗ | ✗ | ✓ |
A hundred and eight questions across six purposes, dealt so that nothing repeats until you have seen the set. You cannot add your own, and a physical deck still beats a phone for passing round a table — but for a meeting, a car journey or a blank page, this is the faster route.