The question we hear most from leaders is “which AI tool should we buy?” It is the wrong first question. Tools are cheap and interchangeable. Readiness is expensive and specific. Here are the six questions we ask before recommending anything.
1. Is your project data in a state a machine can read?
If status lives in slide decks and risks live in people’s heads, an assistant has nothing to work with. Readiness starts with a project tool that is actually used, a risk register that is actually maintained and documents that are actually filed.
2. Is there a process worth automating?
AI amplifies the process it is given. A broken reporting process automated is a broken reporting process delivered faster. Fix the process first, or at least choose a process that is already sound.
3. Can your people brief?
The single biggest predictor of useful output is the quality of the brief. Teams who have been taught a method, such as BRIEF, get value in the first week. Teams left to “play with it” mostly conclude it does not work.
4. Who decides what the machine may and may not do?
If the answer is “nobody yet”, the real answer is “everybody, informally”. A short, clear policy with approved tools and worked examples is a prerequisite, not an afterthought.
5. Does leadership want the truth?
AI-assisted reporting makes delivery more visible. Some leadership teams discover they preferred the fog. Readiness includes a leadership team that wants to see what the data shows.
6. What is the first use case, and is it worth the trouble?
The first use case should be visible, measurable and boring. Status drafting, meeting actions, risk register hygiene. Save the ambitious ideas for after the organization has one unarguable win.
Score yourself in five minutes with our free AI Readiness Score. You get a report by dimension and a suggested first step.
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Choosing your first AI use case in a PMO
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