In a short founder conversation, which diligence questions earn the slot over the others?

## The constraint A founder slot is often short, and the diligence checklist — funding stage and runway, path to revenue, moat, key-person risk, equity context — is longer than the time available. Asking all of it produces a shallow pass: five half-answers, none followed up, and a founder who feels processed. The skill is choosing. ## Two filters, applied in order **Filter one: exclusivity.** Could anyone else in this loop answer it, or could a careful reading of the company's public material? If yes, it does not belong here. Process, tooling and team rhythm belong with the engineers. Stages, timelines and the pay band for the level belong with the recruiter. Anything published belongs to your preparation, and asking it burns credibility as well as time. **Filter two: decision weight.** If you imagine the two most likely answers, would you behave differently? Runway passes easily: fourteen months and a milestone leads somewhere different from seven months and an active raise. 'How big is the market?' fails — you will proceed regardless of the answer, so it is curiosity, not diligence. What typically survives both filters: | Question | Exclusive? | Changes the decision? | |---|---|---| | Months of runway against the next milestone | Yes | Yes | | Who pays today and who pays next | Mostly | Yes | | What slows a well-funded competitor down | Yes | Often | | Which people the product or customers depend on | Partly | Sometimes | | What fraction of the company a grant represents, in shape | Yes | Sometimes | A note on that last row: it is legitimate to ask a founder for the *context* around equity — roughly what share a grant represents and how they expect later financing to affect early employees — but keep it to shape. Plan mechanics differ between companies, and tax and legal treatment varies by country and by personal circumstance, so use the answer as background and get independent advice on your own documents rather than negotiating terms in this conversation. Detailed terms belong with whoever owns the offer. ## Sequencing beats listing Open with the question that is cheapest to ask and richest to answer: **'What keeps you up at night about this business?'** Founders answer it candidly more often than not, and the answer typically lands on one of your checklist rows — the sales cycle, a competitor, a person, the raise. That does two things: it tells you which of your items are already partly answered, and it earns you the right to go deeper on the one they raised rather than switching topics. Then spend the middle on the number: runway against the next milestone. Then keep the last slot **unallocated**, and use it on the strongest thread that opened. A pre-written third question is almost always worse than a live one. ## A worked example Suppose you have a short conversation with a co-founder at an early-stage company selling forecasting models to operations teams. You open with the risk question. They say the models are good but each new customer needs weeks of bespoke data plumbing, so growth is gated on delivery. Your prepared list said: runway, moat, hiring plan, key-person risk. The answer just reshaped it. Moat is partly answered — integration depth is the switching cost, and it is also the drag. So ask the number next: 'How many months does the current plan fund, and what does the next raise depend on?' Say they answer nineteen months, with the raise pinned to a retention milestone. Now your reserved slot has an obvious best use: *is the plumbing cost per customer coming down?* Because if it is not, nineteen months and a retention milestone are in tension, and that tension is the single most decision-relevant thing available to you. Three questions, one of them improvised, and you leave with a coherent picture instead of five fragments. ## The tradeoffs you are actually making - **Depth versus coverage.** Two answers you can reason with beat five you cannot. Coverage feels safer and teaches you less. - **Information versus relationship.** Every hard question spends a little goodwill. Runway is worth it; a fourth financial question usually is not. - **Now versus later.** Some questions are better at the offer stage, when candour rises. Ask now what you need in order to keep going; defer what you need in order to sign. - **What your silence says.** Asking nothing about the business is itself a signal to a founder — it reads as a candidate who has not understood what joining an early-stage company is. ## The failure to avoid The common one is not over-asking. It is treating the founder conversation as a warm culture chat, enjoying it, and walking out without ever asking how long the company is funded for. Whatever else you cut, do not cut the clock.