Founder readiness questions: practical details and examples

Readiness questions get asked all at once, usually late at night, and the answers do not go anywhere. The useful version is smaller: a short set attached to each decision, asked at the moment that decision is in front of you, and answered in writing.

What follows is arranged by gate rather than by theme, and it assumes you already know what readiness actually consists of. Nothing here asks how confident you feel, because that answer carries no information.

What to take away

• Ask the questions that gate the next decision, not all of them at once. Most have no answer yet and do not need one.
• A good readiness question has an answer someone else could check. If yours can only be answered by a feeling, rewrite it.
• The questions get harder as the commitments get less reversible, which is the right way round.

Gate one: before the first conversation

These cost nothing and prevent most of the wasted months.

• Who exactly has this problem, described so that someone else could find twenty of them by Friday?
• How will I reach them without an introduction I do not have?
• What am I hoping to hear, and what would I have to hear to be disappointed?
• What do these people do about it today, and what does that cost them?

The third one is load-bearing. If nothing anyone could say would disappoint you, the conversations are not going to produce information.

Gate two: before you spend money

Money spent before this gate is nearly always spent on the feeling of having started.

• What specific thing will I know after this spend that I do not know now?
• Could I get the same answer for less, more slowly?
• What is the notice period, and what does leaving cost?
• If this turns out to be wrong, what does the failure cost me in total: money, months, and standing with people I will need later?

Ask the fourth one out loud. Written down it is a budget line. Said aloud it is a decision. Most of what gets bought at this gate could have been replaced by a smaller offer put in front of a real buyer.

Gate three: before you leave your income

• What has to be paid every month whatever happens, counted honestly?
• How many months can I cover from money already set aside, not money I expect to earn? The SBA's guide to funding a business is worth reading first, mostly to see how few of the routes apply before there is any trading history.
• What can I lose entirely without a consequence I would refuse to accept?
• How long would it take to get back to earning what I earn now, and what would I have to keep current to make that possible?
• Who else is affected, do they know the real number, and have they agreed to it rather than been told?

The last one ends more ventures than any commercial mistake. Agreement in month one is cheap. Discovery in month eight is not.

Gate four: before you bring in another person

• Who decides what, in the cases where we disagree?
• What is each of us committing, in hours and in money, and by when?
• How is ownership earned over time rather than granted on day one?
• What happens if one of us wants out, and who buys whom?
• Which of the three jobs is nobody covering: wanting it enough, selling it, and making it?

Write the answers while everyone is optimistic. The same conversation later happens with something at stake and a lawyer in the room.

Questions that sound rigorous and are not

The question	Why it produces nothing	Ask instead
Would you use this?	Measures politeness and costs the answerer nothing	What did you do the last time this came up?
How much would you pay?	Invites a guess presented as a fact	What did you spend on this last year, and on what?
Is the market big enough?	Four questions in one, answered as though it were one	Who can I reach, through what channel, at what cost?
Am I passionate enough?	Unfalsifiable, and no help on the hard days	Will I still be making these calls in month seven?
Is now the right time?	Timing is not knowable in advance	Is the first commitment small enough that timing does not decide it?
Do I have enough experience?	Too broad to act on	What am I actually missing: access to buyers, or the ability to deliver?

The pattern in the right-hand column is the same each time: swap a judgment for something observable. That the left-hand versions produce confident and useless answers is not a founder problem either; how heavily wording moves an answer is set out in the guidance on writing survey questions. Market validation does the same trick with a bigger question.

How to answer them

In writing, dated, in one place. Not because the document is valuable, but because written answers are much harder to revise quietly than remembered ones, and quiet revision is what turns a stopping condition into a permission slip.

Answer only the gate you are at. Half of these have no answer at the start, and that is not a failure. A blank next to "how will I reach them" is a task, not a verdict.

Then give one person outside the venture your gate three and gate four answers. Not a co-founder, who has your incentives. Somebody with nothing at stake, who will ask you about the number in four months.

Common questions

What if I cannot answer most of these?

Then you are early, which is the normal state. The list becomes a work queue: each blank is something you can go and find out, and almost all of it is cheap. None of it requires you to have built anything.

Should I answer them again later?

Answer gate one every time you enter a new segment, because the audience changed even if the idea did not. The money questions want a fixed review date, and monthly is enough. The rest are answered once per decision.

Who should I not ask for help with these?

Anyone whose approval you want. That includes most friends and family, who will answer the question they think you are really asking. Situations you will recognize shows how that support gets mistaken for evidence.

Is there a threshold that means I am ready?

No, and any tool offering one is scoring your own inputs back at you. Readiness is a set of arrangements: a loss ceiling written down, a stop rule someone is holding, and the irreversible commitments postponed. The tools worth using are the ones that keep those honest.