20 Questions to Ask Before Starting a Business
Twenty questions to answer honestly before you spend money on a business idea, covering who has the problem, what they will pay, how many customers cover your living costs, when cash actually arrives, and what would make you stop.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
Who has this problem badly enough to have tried to solve it already?
A person paying for a bad workaround, a spreadsheet, an agency, a part time assistant, has proved the problem is worth money. If nobody has attempted a fix, you may be looking at an annoyance rather than a need.
- 2
Can I name ten specific people or businesses who would buy this?
Named prospects are a market, adjectives are not. If your list is a category like small businesses or busy parents rather than ten names, the first job is research, not building.
- 3
Have I asked twenty of them and written down what they actually said?
People are polite about ideas and specific about problems, so the useful notes are the complaints in their own words. Anyone who says it sounds great without asking the price has told you nothing.
- 4
What will someone pay, and how did I arrive at that number?
A price built from your costs plus a margin ignores whether the value is there. Working back from what the problem costs them today is the only pricing that survives contact with buyers.
- 5
How many sales do I need each month to cover my own living costs?
This one number turns a vague dream into a testable claim. If it takes hundreds of small transactions, your marketing problem is much larger than your product problem.
- 6
What does it cost me to get one customer, and how do I know?
Guessing this is how businesses with good products run out of money. Spend a small amount on a real test before you build anything expensive.
- 7
How long between doing the work and being paid for it?
Profitable businesses fail on timing, especially when clients pay in sixty days and staff are paid weekly. Map the gap in weeks and fund it deliberately.
- 8
What is the smallest version of this I could sell within a month?
Something manual, ugly and narrow will teach you more than six months of building. If the smallest version still takes a year, you have chosen a hard first business.
- 9
Why has nobody I respect already done this?
There is usually a reason: regulation, thin margins, a brutal customer, or a distribution channel locked up. Finding the reason is not discouragement, it is the actual work.
- 10
Who is the competitor my customers would name if I did not exist?
The honest answer is often a spreadsheet, a friend of a friend, or doing nothing at all. Competing with nothing at all is harder than competing with a company.
- 11
What do I do better than the obvious alternative, in one plain sentence?
If the sentence needs a diagram or three clauses, customers will not remember it. Cheaper and faster and better usually means you have not chosen yet.
- 12
How much money can I lose before it damages my life?
Naming the figure in advance stops the slow escalation of putting in a bit more. It also tells you whether this should be a side project for now.
- 13
Am I funding this from savings, borrowing, or someone else's money?
Each option changes who you answer to and how fast you must move. Borrowing against a home turns a business decision into a family one, so say that out loud.
- 14
What am I going to stop doing to make room for this?
Adding a business to a full life without subtracting anything is how both suffer. If nothing can go, the honest plan is a slower start.
- 15
What is the job I am worst at that this business requires?
Every business has one activity you will avoid, usually selling or bookkeeping, and avoidance quietly kills it. Decide now whether you learn it, pay for it, or pick a different business.
- 16
Who will tell me the truth about how it is going?
Friends encourage and customers go quiet, so you need one person who will say the numbers look bad. Name them before you start.
- 17
What would make me shut this down, and by when?
A written threshold, a date and a number, is what separates persistence from denial. Setting it while you are calm is the only time you can.
- 18
What legal or tax obligations start the moment I take the first payment?
Registration, sales tax, insurance and licensing vary by trade and place, and back-dated problems are expensive. An hour with an accountant now is the cheapest hour you will buy.
- 19
If this works, what does my week look like in two years?
Some successful businesses produce a life you would not choose: constant travel, weekend shifts, twenty staff. If you would refuse the successful version, change the plan now.
- 20
Do I want this business, or do I want out of my current job?
Both are legitimate, but they lead to different decisions and only one of them survives a hard second year. If it is escape, look honestly at the cheaper exits first.
Pressure-Testing the Idea
Practical guidance for the conversation itself.
How to Use These Questions
How to Use These Questions
Answer in Numbers Where a Number Exists
Price, customers needed per month, cost to acquire one, months of runway. An answer like enough to be worth it is a way of avoiding the arithmetic that decides whether this works.
Have Someone Else Ask Them
Read your answers aloud to a person who is willing to be unimpressed, ideally someone who has run a business. The questions you rush past are the ones to go back to.
Do the Cheapest Test First
Before building, try to take one payment for the manual version. A single customer who pays is worth more than fifty people who said they would.
Separate the Idea From the Escape
Wanting to leave a job is a good reason to change something and a poor reason to choose a particular business. Work out which one is driving the timeline.
A Sensible Order to Work In
A Sensible Order to Work In
- 1Write down the problem in the words a customer would use, not the words you would use.
- 2Find twenty people with that problem and ask what they do about it today and what it costs them.
- 3Set a price and try to take money for the smallest useful version.
- 4Build the monthly numbers from your own quotes: rent, wages, tools, insurance, tax.
- 5Work out how many customers cover your living costs and how you would reach that many.
- 6Decide your maximum loss and the date you review it, then write both down and tell someone.
Where Plans Usually Break
Where Plans Usually Break
Confusing Interest With Demand
Encouragement, sign-ups and likes are free. Nothing counts as validation until money changes hands or a contract is signed.
Ignoring the Gap Between Work and Payment
Businesses with full order books fail because the cash arrives later than the bills. Model the weeks, not just the annual totals.
Building Before Selling
Long build phases feel productive and postpone the only question that matters. Sell first, even if you have to deliver it by hand.
No Stopping Rule
Without a written threshold, every bad month becomes an argument for one more month. Decide the exit conditions while nothing is at stake.