A signed pilot feels like progress. It has a logo attached, a start date, and a shared channel, and it is the most reliable way we know for a young company to spend a year learning nothing.
The failure mode is structural rather than personal. A pilot is cheap for the buyer and expensive for you: they risk a small budget line and some calendar time, while you risk your roadmap, your engineers, and the eventual shape of your product. When the incentives are that asymmetric, the default outcome is an indefinite extension and a warm reference.
So we ask for the boring things before the interesting ones. Who signs if this works? Which number has to move, and who is accountable for it today? What happens on the date it ends? A buyer who cannot answer those is not evaluating a purchase — they are holding a free option, and the honest response is to decline it politely.
Real traction has a recognisable shape: someone with authority, a number they are measured on, and a date. Everything else is a very well-attended conversation.