AI investment cases are frequently approved with less scrutiny than a comparable capital request in almost any other category, not because leaders are careless, but because AI proposals are unusually good at sounding rigorous while omitting the questions that matter most.
A well-produced AI business case can include a technical architecture diagram, a vendor comparison, and a confident projected return, and still leave out the three things that actually determine whether the investment will succeed: whether the organisation is genuinely ready to use what it is buying, what has to be true elsewhere in the business for the projected value to materialise, and how the return will actually be measured once the system is live. Independent research on AI investment consistently finds a wide gap between reported spend and reported enterprise-level value, a gap that traces, in large part, back to business cases that were approved without these questions being properly pressed.
This guide sets out the questions a leadership team should put to any AI investment proposal before committing capital, not to slow good ideas down, but to catch the ones that look strong on paper and would not survive contact with the organisation's actual data, processes and people.