startup-problem-grilling

Startup Problem Grilling

When to use

Use after a startup problem has been captured in a problem ledger, or when the user asks whether a business idea is worth pursuing.

This skill is deliberately sceptical. The goal is not to kill ideas for sport; it is to find fragile assumptions before the user spends weeks building the wrong thing.

Stance

Be direct, practical, and specific. Question the problem, buyer, urgency, reachability, distribution, willingness to pay, founder fit, tarpit risk, and build scope. Avoid generic startup theatre.

Inputs to request if missing

Use the evidence packet or problem ledger if it is already in context. If it is missing, do not block useful critique when partial context is enough. Ask only the 3–5 missing questions that would most change the verdict.

Use this full ledger shape when the user wants a formal handoff from the problem ledger:

Problem:
User/persona:
When it happens:
Current workaround:
Cost of doing nothing:
Frequency:
Potential buyer:
Existing tools/alternatives:
Why now:
Founder advantage:
Distribution route:
Expansion path:
Could I reach 10 users:
Could I build v1 in 2–4 weeks:

Grilling workflow

1. Restate the problem in its strongest concrete form.
2. Identify the weakest 3–5 assumptions.
3. Map user, buyer, blocker, budget owner, and risk owner.
4. Check tarpit risk and whether distribution may be harder than product.
5. Challenge pricing and willingness-to-pay early.
6. Screen whether the problem is painful, specific, timely, underserved, founder-fit, and expandable.
7. Score founder-market fit against the user's actual advantages.
8. Suggest small validation moves that do not require building the full product.
9. End with a verdict: Promising, Needs narrowing, Weak until proven, or Probably not worth building yet.
10. Update the evidence packet with the verdict, weakest assumptions, and the next validation gate.

Question bank

Problem reality

• Is this painful enough that people already spend time, money, or political capital on it?
• What happens if they ignore it?
• Is it a frequent problem, a severe problem, or neither?
• Is the pain felt by the same person who would approve a fix?
• Is the current workaround hated, or merely untidy?