20 questions to pressure-test an idea before you commit

Most ideas don't fail because nobody had doubts. They fail because the doubts stayed vague: "I'm not sure about the budget", "people might not show up". Pressure-testing turns those feelings into questions you can actually answer, before you've spent the time or money.

These questions are grouped by what they test. You won't need all of them. Pick the three or four that make you most uncomfortable; those are usually the right ones.

What it rests on

Every idea assumes things. These questions drag the assumptions into the open.

1. What has to be true for this to work that I haven't checked?
2. Which of those, if it turned out false, would kill the idea outright?
3. What am I assuming about other people's time, money or interest?
4. Am I treating a "maybe" as a "yes" anywhere? (A neighbour who said "sounds fun" is not a volunteer.)

Who it's for

5. Who, by name or by a specific description, has this problem today?
6. What do they do about it now, and why would they switch?
7. Who would be annoyed or worse off if this happened?

How the parts fit

8. Which part has to happen first, and what's waiting on it?
9. Is there one open question blocking several other decisions?
10. Where do two parts of the plan pull against each other? (A tight timeline and a volunteer team often do.)

What it costs

11. What's the smallest version that would still be worth doing?
12. What does it cost in time each week, not just money up front?
13. What would I stop doing to make room for this?

What could go wrong

14. If this failed a year from now, what's the most likely reason?
15. What's the risk I keep not writing down?
16. What would I do if the biggest assumption turned out wrong halfway through?

How I'll know

17. What would I need to see in the first month to keep going?
18. What would make me stop, and have I decided that in advance?
19. Who has to say yes, and have they?
20. What's the one thing I could find out this week that would make this decision easier?

Make the questions specific

A generic question gets a generic answer. "Who is your audience?" invites a paragraph about "people who care about sustainability". The fix is to tie each question to something in your actual notes:

Generic	Specific
Who is it for?	Does the school want two beds for the whole season, or just the spring term?
What could go wrong?	If the backflow valve the city wants costs more than the $800, what goes?
Is there demand?	Of the 12 households who said "maybe", how many would pay $20 for a plot?

If you can't make a question specific, you may not know enough about that part of the idea yet. That's a finding too.

Answer them in writing

Thinking about a question isn't the same as answering it. Write a sentence for each one you picked. Short answers are fine; "don't know yet" is fine, as long as you also write down how you'd find out. Those written answers are what turn a hunch into a plan, and they're easy to share with whoever needs to say yes.

If you're brainstorming with an AI, the same questions work as prompts, with one rule: make it keep your answers separate from its suggestions. Our guide on brainstorming with AI without losing your own ideas covers how. And when you're ready to sort the whole thing into a plan, see how to turn a brain dump into a plan.