Competent executives make surprisingly bad technology purchases
Competent executives make surprisingly bad technology purchases, and it is not a judgment problem. It is an information problem that looks like a judgment problem.
An owner who has bought trucks, leased buildings and hired a CFO knows how to buy. They know what a fair price looks like, what a warranty is worth, and when a salesman is stretching. That knowledge came from decades of feedback: buy, use, see what happens, adjust.
Software gives no such feedback. The owner buys a system every seven years, cannot inspect it before purchase, cannot see inside it after, and gets the result eighteen months later mixed up with a dozen other changes. There is no way to learn the way they learned trucks.
Meanwhile the vendor sells this exact product every week, knows every objection, and knows precisely which promises cannot be checked.
Normal executive judgment relies on being able to independently evaluate at least part of what is being claimed. Remove that, and judgment becomes trust, and trust goes to whoever is most fluent in the room.
This is why the same executive who negotiates a lease down to the dollar signs a $500k implementation on a demo and a reference call. Not carelessness. There was nothing else to hold on to.
The fix is to borrow the feedback loop someone else has: a person who sees these decisions often enough to recognise the shape of a bad one before the money moves.