Fifteen questions that feel awkward now and prevent the disaster later. Have this before any equity is discussed.
15 min read · Level 1
Every one of these questions gets answered eventually. The only choice is whether that happens now, over two calm hours, or in eighteen months during a crisis with money on the table and lawyers copied in. Founders who skip it are not avoiding the conversation — they are deferring it to the worst possible moment and paying interest. If someone will not discuss equity and failure before you start, that is your answer.
A structured, deliberately uncomfortable conversation covering motivation, money, commitment, roles, decisions, failure and exit — before any equity is agreed.
Set aside two hours. Both people answer every question out loud.
Because every one of these questions will be answered eventually. The only choice is whether that happens now, calmly, or in eighteen months during a crisis with money on the table.
Founders who skip it are not avoiding the conversation. They are deferring it to the worst possible moment.
The questions, in five groups.
Motivation
Money and commitment
Roles and decisions
Ambition
Failure and exit
The last question is the one people most want to skip. It is the most important one on the list.
First-time founders often have a warm, general version of this — 'we're both really committed' — and mistake agreement in tone for agreement in substance.
Ask for specifics. 'I'm committed' is not an answer; 'I'm handing in notice on the 14th and I have eleven months of savings' is.
The second mistake: having the conversation and not writing it down. Memory diverges, particularly about equity and roles.
Two hours, not over drinks, not squeezed between other things. Say in advance that it will be uncomfortable and that that is deliberate.
Not a questionnaire. The hesitations and qualifications are much of the information.
Dates, numbers, names. 'Soon' and 'committed' are not answers.
Roles, decision rights, salary expectations, what happens if someone leaves. A shared document, same day.
If someone will not engage with the equity or failure questions now, that is your answer. It will not improve under pressure.
The conversation is the value; the document records it. Both are needed.
Before agreeing equity, and ideally before the trial project too.
Never skip it, including with a close friend or a former colleague. Especially then — familiarity is exactly what makes people assume alignment they have not checked.
"If you left, what should happen to your equity?" is consistently the hardest item on the list to raise and the most consequential to have settled. Agreeing it while everyone is optimistic is straightforward; agreeing it while someone is walking out is close to impossible.
Raise the departure question explicitly. Willingness to discuss it calmly is itself the most useful signal in the conversation.
Vague commitment reliably becomes absent commitment. The founders who avoid this ask for specifics instead: the notice date, the months of savings, the financial obligations. Warm general agreement and hard specifics feel similar in the room and behave completely differently a year later.
Convert every reassurance into a date or a number. If it cannot be converted, it was not a commitment.
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