03 · Select Converge ✦ AI plays: Critic

Hundred Dollar Test

Give everyone $100 of pretend money to spend across the ideas, and see where it really goes.

Best for
Fast group prioritizingshortlists of 4–12 ideas, features or projects
Time
10–20 minutesplus a few minutes to discuss
People
Best in a teamfrom 3 people to a whole room
Difficulty
Beginnerexplained in one sentence
Origin
Classic facilitation methodused in workshops, product teams, budgets
01 What it is

Put your money where your priorities are.

Ask a group to rate ideas from 1 to 5 and almost everything ends up a 3 or a 4. Give each person $100 of pretend money to spend on the ideas they believe in, and the picture changes. The budget is fixed, so every dollar placed on one idea is a dollar not placed on another. People suddenly have to choose.

Each person divides their $100 however they like: all of it on one idea, or spread across several. Add up the totals and the group's real priorities appear, including how strongly people feel, which a show of hands can't capture. Then talk about the surprises before you decide.

Use it when you have a manageable shortlist and need a quick read on priorities, when ratings keep coming out the same, or when you want quiet people's preferences to count as much as the loudest voices.

8 members × $100Tool library$230Kids' growing club$180Rain barrels$150Pollinator strip$110Compost workshop$80Pizza oven$50

A community garden's eight members spent $100 each. The top two ideas drew more than half the money.

1

Prepare the shortlist

4–12 clear, distinct options

Which options are on the table, and does everyone understand each one?

  • Is each option written as one clear line?
  • Have near-duplicates been merged?
  • Is the list short enough to weigh, ideally 12 or fewer?
Food pantrySeven ideas, from evening opening hours to a fresh-produce fridge, each on its own card.
2

Set the spending rules

Budget, limits and what a dollar means

What does a dollar stand for, and are there any limits?

  • Does $1 mean value, urgency, or what you'd fund with real money?
  • Can people put all $100 on one idea, or is there a cap?
  • Can people spend on their own ideas?
Food pantry$100 each in $10 steps. Spend it any way you like, even all on one idea.
3

Spend in private

Everyone allocates at the same time

If this were your own money, where would you put it?

  • Spend silently first, so no one copies anyone
  • Use slips of paper, sticky notes or a quick online form
  • Check that your spending adds up to exactly $100
Food pantryTwelve volunteers fill in slips at the same time and drop them in a box.
4

Add up the totals

See where the money went

Which ideas attracted the most money, and how spread out is it?

  • Rank the options by total dollars
  • Note how many people funded each idea, not just how much
  • Look for ideas with a few big backers
Food pantryProduce fridge $420, evening hours $360 … text reminders $40.
5

Discuss the surprises

Talk before you decide

What does the spread tell you that a simple vote wouldn't?

  • Which result surprised you, and why?
  • Did anyone put a lot on an idea nobody else backed?
  • Does nothing stand out? Run a tighter second round
Food pantryOne volunteer put all $100 on a wheelchair ramp. Her reason moved it into the plan.
6

Decide and record

The tally is evidence, not a verdict

What will you take forward, and why?

  • Do the top ideas still make sense against your goal?
  • Do any low scorers deserve a second look?
  • Who makes the final call, and how will you share it?
Food pantryFund the fridge now, trial evening hours in spring, and get prices for the ramp.
02 Why it works

Why pretend money gives real answers

The Hundred Dollar Test is quick and a little playful, but it fixes several problems with ordinary rating and voting.

1

A budget forces trade-offs

When you rate ideas one at a time, you can like them all. A fixed budget makes every choice a trade-off: funding one idea means not funding another. That's how real decisions work, so the result is closer to what people would actually choose.

2

It shows strength of feeling

A show of hands records only yes or no. Dollars show intensity: one person putting $70 on an idea tells you something a single vote never could. You see both how many people care and how much.

3

Every voice counts the same

Everyone gets exactly the same budget, and spending in private stops people simply following the boss. Quiet members' priorities show up on the tally as clearly as anyone else's.

4

It feels like a real choice

Everyone already knows how to spend a budget. Framing the decision as an investment makes people ask would I really back this? instead of do I like it?, and that question tends to produce more careful, honest answers.

03 How to use it

Run a Hundred Dollar Test in five steps

  1. Prepare the shortlist 5 min

    Write each option as one clear line and make sure everyone understands it. Merge duplicates. The test works best with four to twelve options; thin a longer list first with Negative Selection.

  2. Set the rules 2 min

    Everyone gets $100. Say what a dollar means, such as “where you'd invest if it were your own money”, and agree on any limits, such as whole $10 amounts or a cap per idea. Settle this before anyone spends.

  3. Spend in private 5 min

    Each person divides their $100 on paper, sticky notes or a quick online form. Silent, simultaneous spending stops people copying the most senior person in the room.

  4. Tally and show 5 min

    Add up the total for each option and show the results as a simple bar chart. Note how many people backed each idea, as well as how much money it drew.

  5. Discuss and decide 10 min

    Ask what surprised people, and listen to anyone who bet big on an outsider. If no idea stands out, run a second round with tighter rules, such as backing only two ideas each. Then decide.

✓Do

  • Keep the list short and every option clear
  • Spend privately, then reveal together
  • Ask big backers of outsiders to explain why
  • Treat the tally as evidence, not the decision

✕Avoid

  • Running it on 40 ideas at once
  • Letting people see others' spending first
  • Mixing big projects and tiny tweaks on one list
  • Ignoring an idea that a few people funded heavily

What you need

Option cards on a wall, play money or sticky notes for each person (or an online form), a calculator and 20 minutes. With AI, use the prompt below.

04 Worked example

The Hundred Dollar Test in action: a garden's next season

The challenge

“We have six good ideas for next season and the energy to do maybe two of them well.”

Group: a community garden run by eight volunteer members. Goal: choose the projects for next season. Rules: $100 each, in $10 steps, any split allowed, spent in private.

6 ideas · 20 minutes
1
The shortlist

A tool library, a kids' growing club, rain barrels, a pollinator strip, a compost workshop and a pizza oven, each written on its own card.

2
The rules

Everyone got $100 in $10 steps. A dollar meant: “I'd give up my own Saturdays to make this happen.”

3
The spending

Members filled in their slips at the same time. One put all $100 on the tool library; most spread theirs across three ideas.

4
The tally

Tool library $230, kids' club $180, rain barrels $150, pollinator strip $110, compost workshop $80, pizza oven $50.

5
The surprise

The pizza oven had been the loudest idea in meetings, yet only two members funded it. The kids' club was a quiet newcomer's suggestion.

The decision

The tool library and kids' club go ahead. Rain barrels wait for a grant, and the pizza oven becomes a one-off fundraiser idea.

05 ✦ Go AI

Make every dollar count with an AI critic

AI can't spend your group's money for you, and it shouldn't: the point of the test is to reveal what your people value. Where it helps is before and after. It can turn a messy list into clear options, model how different people might spend, and question the result so you notice what the tally hides.

YouYou bring

  • A short, agreed list of real options
  • Your group's private, honest spending
  • What the result means in your context
  • The decision, and how you explain it

AIAI brings

  • Clear, comparable wording for every option
  • Spending rules suited to your group and list
  • Simulated splits from different stakeholders
  • Questions about what the totals might hide
MOVE 01

Level the field

Rewrite every option at the same size and detail, so none wins just by sounding better.

Rewrite these 8 options as one neutral line each, at the same level of detail, without selling any of them.
MOVE 02

Stakeholder spend

Ask how people who aren't in the room might spend, then check with them.

How might a parent, a retiree and a new member each split $100 across our list? Give a reason for each.
MOVE 03

Read the tally

Get help seeing the shape of the result: broad agreement, split camps or a passionate few.

Here are our totals and how many people backed each idea. What patterns do you see, and what should we ask?
MOVE 04

Tiebreak round

Design a sharper second round when the money is spread too thinly.

Our top four are within $30 of each other. Design a second round with rules that force clearer choices.

Watch out for

  • AI's spending isn't your group's. Simulated splits are a warm-up, never a substitute for real ones.
  • Big totals can hide big doubts. Ask what the money didn't capture: risks, costs, fairness.
  • Don't let AI pick the winner. The tally informs the decision; your group owns it.
  • Keep individual spending private. Share totals with AI, not who spent what.
06 Your prompt

Your Hundred Dollar Test coach, ready to paste

List your options, pick a mode, then copy the prompt into Claude, ChatGPT, Gemini or Copilot. In coach mode the AI helps you prepare the list and the rules, waits while your group spends, then helps you read the results.

1 · Describe your challenge

The more specific you are, the better the result. The prompt updates as you type.

2 · Choose a mode

hundred-dollar.prompt
3 · Paste it into any AI assistant, or open it directly: Open in Claude ↗ Open in ChatGPT ↗

The “Open in” links put the prompt in the web address. If your challenge includes anything sensitive, copy and paste instead.

Keep going: follow-up prompts

After the session, click one to copy it, then paste it into the same chat.

Keep exploring

Tools that pair well with Hundred Dollar Test