Pivot, Persevere, or Shut It Down?

The first 10 questions

This is where the conversation starts. Each answer shapes what gets asked next.

1. 01What did you launch, when, and to whom? What did you expect to happen by now — and what actually happened?
2. 02Walk me through the real numbers — signups, activation, retention, revenue, growth rate. Not the flattering cut: the honest one.
3. 03How long have you been at this, and what's left in the tank — money, runway, and personally?
4. 04What have you already tried to fix it — messaging, pricing, features, channels — and what did each attempt actually change?
5. 05What do your best users have in common — is there a segment where it genuinely works? What would the business look like if that segment were the whole market?
6. 06When users leave or never activate, do you know why? What do churned users and lost deals actually say — and have you asked them?
7. 07Is the problem the idea, the execution, or the distribution? What evidence separates those — and what would you need to learn to be sure?
8. 08Be honest: what result in the next 60–90 days would make you confident to persevere — and is that result plausible given the trend, or a hope?
9. 09If you pivot: pivot to what? Is there a specific insight from this attempt pointing somewhere, or would you be starting from zero with extra baggage?
10. 10What does another six months cost — money, opportunity, relationships, your own conviction? What would you do with that six months if this project didn't exist?

+ 4 more questions across discovery, validation, and the creative brief — each one adapting to what you've already said.

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