interview-the-founder

---
name: interview-the-founder
description: Use when running a founder meeting or generating the questions you'd ask — the texture of the conversation, not a diligence checklist. Triggers: prepping for a pitch meeting, "what would a VC ask", reviewing a deck to reverse-engineer the live questions.
---
# Interview the founder — a conversation, not a checklist

The questions are the *what*; the *how* is the whole point. A topic checklist handed over flat is the
slop this discipline exists to avoid. Generate questions that sound like a person on a walk.

## The room
- **Open warm and human**, then get to it. You'd rather have a conversation than sit through slides — so
  you're not hearing the deck they gave thirty other investors. Be self-deprecating, disclose conflicts
  up front; the warmth is real and it's also how you get the real answers.
- **Empathize with the leap** — "nobody leaves a great job to do this" — which is itself a way of testing
  the pull.

## The dig
- When something matters, **push, and narrate that you're pushing**: "the long term makes sense, but I'm
  pushing you — short term, what's the wedge?"
- Keep going past the first answer. The **four-follow-up test** is the game: real secrets get *more*
  specific under pressure, fakes get vaguer (`test-earned-secrets`).
- **Triangulate demand sideways** — never "is there demand," always "what were they using before?" and
  "what's the last customer who said no, and why?" (`read-revealed-preferences`).

## Signature moves
- **Fast-forward time** to test latitude — "18 months, five years from now — what *is* this?"
- **Say the bar out loud** — "you need a unique insight, two of three: tech, market, or GTM."
- **Reach for an analogy** to find the truth (core editor vs. viewer; fundraising as dating; jazz tempo).
- **Separate acceptability risk from tech risk** on physical/bio/regulated bets.
- **Close by offering help and listening to the ask** — "where can we be helpful?" How self-aware and
  coachable the ask is tells you as much as the pitch.

## Anti-patterns
- Handing over a generic product/market/tech checklist and calling it a lens.
- Interrogating instead of conversing — the goal is to amplify, not to win.
- If you have to **drag** the good answer out of the founder, read that as a flag, not a detail.