The conversation to have before you commit

Fifteen questions that feel awkward now and prevent the disaster later. Have this before any equity is discussed.

What is it?

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.

Why does a founder care?

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.

Example

The questions, in five groups.

Motivation

  • Why do you want to do this specifically?
  • What would make this a success for you personally?
  • What would you do if this failed in two years?

    • Money and commitment

  • What salary do you need, and when?
  • How long can you go without one?
  • What are your financial obligations?
  • Are you leaving your job? When exactly?

    • Roles and decisions

  • Who decides when we disagree? On product? On hiring? On money?
  • What is each of us responsible for?
  • What happens if one of us is consistently not delivering?

    • Ambition

  • Would you sell for $8M in two years?
  • Do you want to raise venture money?
  • What does this look like in five years?

    • Failure and exit

  • What would make you want to leave?
  • If you left, what should happen to your equity?

    • The last question is the one people most want to skip. It is the most important one on the list.

    The common mistake

    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.

    How it works

    Step 1: Schedule it properly

    Two hours, not over drinks, not squeezed between other things. Say in advance that it will be uncomfortable and that that is deliberate.

    Step 2: Both answer every question aloud

    Not a questionnaire. The hesitations and qualifications are much of the information.

    Step 3: Push for specifics

    Dates, numbers, names. 'Soon' and 'committed' are not answers.

    Step 4: Write down what you agreed

    Roles, decision rights, salary expectations, what happens if someone leaves. A shared document, same day.

    Step 5: Notice avoidance

    If someone will not engage with the equity or failure questions now, that is your answer. It will not improve under pressure.

    Step 6: Turn it into a founders agreement

    The conversation is the value; the document records it. Both are needed.

    When to use this

    Before agreeing equity, and ideally before the trial project too.

    When not to use it

    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.

    Do this now

    Apply this to your own startup in My Full Journey (free account).