Before your next technology investment, ask someone who gains nothing
Before your next major technology investment, ask one person who does not make more money if you say yes.
Count the people who have been involved so far. The vendor's sales team. The implementation partner. The agency. The internal champion whose project it is. Perhaps a consultancy that helped with the strategy. Every one of them is paid, promoted, or proven right by a yes.
That is not corruption. It is how the market is built. Nobody sells "no."
But it means the owner has been receiving advice exclusively from one side of the transaction, and has been calling it due diligence.
The missing voice is cheap to add. A board member with operating experience. A peer owner who made the same decision three years ago and will tell you what they would not repeat. Someone whose fee is fixed and whose next engagement does not depend on this one proceeding.
Give that person the proposal, the alternatives, and an hour. Ask them one thing: if this were your money, would you sign, and what would you want to know first?
The answer might be yes. Often it is, and you proceed with better questions answered. Sometimes it is "not like this," and the version you sign a month later is smaller, cheaper, and yours.
Either way, for the first time in the process, somebody has read the decision from your side of the table.