The questions a CEO should ask in the approval meeting
The CEO does not need to understand the technology. They need to know which questions expose a bad decision. These are the ones I would ask in the approval meeting.
What happens if we do nothing for a year? If nobody can price it, there is no business case yet.
Which number moves after go-live, and who is accountable for it moving? Not "efficiency." A number on a report someone already reads.
Who recommended this, and how are they paid if we say yes?
What did the estimate assume about us, and what happens to the price when an assumption is wrong?
What can we not undo once we sign? Data model, contract term, custom code we own or do not own, the vendor's access to our systems.
What is the smallest version of this that would tell us whether the big version is right?
Who owns this after launch? A name, not a department.
None of these require technical knowledge. Every one of them requires the person answering to have done work they may not have done. A good proposal survives all seven. A bad one usually breaks on the second or the fourth, and it breaks before any money has moved, which is the whole point.