How to use this list
Running 47 questions without turning a sales call into an interrogation.
Do not read all 47 down a call. You will sound like a procurement form and you will learn less, because the useful signal is in how someone thinks, not in whether they have a prepared answer.
Pick twelve
Choose two or three from each section that map to your actual risk. If you are non-technical, weight ownership and quality. If you have a hard deadline, weight price and process. If the provider is a team rather than a person, weight who does the work.
Ask the open ones first
Start with question 1 — "describe my product back to me in one sentence." It is the highest-signal question in the list and it takes ten seconds. Someone who repeats your feature list has not understood the product. Someone who tells you what it is for, and what they would cut, has.
Listen for the shape of the answer, not the content
- Specifics beat reassurance. "Yes, we handle that" is not an answer; "here is how we handled it on X" is.
- Volunteered downsides are the strongest possible signal. Anyone who tells you unprompted what could go wrong has done this before.
- Watch for the pivot to sales. A question about ownership answered with a paragraph about their process is a no.
- A slow, honest "I do not know, I would need to check" beats a fast confident wrong answer every time.
Get the answers in writing
For anything in the ownership and price sections, ask for the answer by email afterwards. It is a reasonable request, it takes them two minutes, and a provider who will not put an ownership answer in writing has told you what you needed to know.
