A signed pilot is the best news a young venture gets before its first sale. Someone with a budget and a calendar has agreed to try the thing on real work.

Then, somewhere between the handshake and the kickoff call, it starts getting counted as revenue that hasn’t arrived yet.

What it proves

Be exact about what was agreed. An organisation decided your idea was worth some of its people’s time, inside its own walls, for a few weeks. The agreement proves you reached someone who could say yes to something. It proves the problem is real enough for them to spend attention on. And it gives you the one thing a demo never can: the product meeting an ordinary working day.

None of that existed last month. All of it is worth having.

What it can’t prove

A pilot says nothing yet about whether they’ll pay. Committing people’s time and approving expenditure are different decisions. It says nothing about who signs the purchase order, and that’s rarely the person who signed the pilot. It says nothing about whether the people using it would miss it if it were to go away tomorrow.

In the corporates I worked in, a manager could say yes to trying something. Spending money on it went up the chain, and the higher it went, the more differently it was read.

A pilot is a loan of attention. A contract is a transfer of money.

The question to ask before day one

Before the kickoff, ask one question and get the answer in writing: if this works, what happens next, and who decides?

You want three things: a named buyer, a budget line and a date.

If they can answer, the pilot has a path to becoming a sale. If they can’t, you’re running a free trial for a department that likes trying things.

Then agree what success looks like before the first day, not after the last. A pilot judged afterwards drifts towards “it went well”, and “it went well” has never been turned into an invoice.

Celebrate the pilot for what it is: proof someone will give you their time. Then make them tell you what would make it worth their money.

Want more like this? Rick writes about the go/no-go decision, founder counterintuitions, and the business of building ventures worth building.

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